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Dudleytown Historic District

Guilford Town, New Haven County, CT

The Dudleytown Historic District was listed on the National Register of Historic Places in 1991. Portions of the content on this web page were adapted from a copy of the original nomination document. []


The Dudleytown Historic District is located approximately a mile and a half northeast of the Guilford town center, straddling the East River. The spine of the Dudleytown Historic District is Clapboard Hill Road, which runs through the district for 1.4 miles. Houses front on the road in a rural setting, with fields behind them and extensive wetlands in the river valley. The houses were built as farmhouses by members of the Dudley family in the 18th and 19th centuries and are now well preserved as residential properties and conservation land. Many are still owned by Dudley descendants.

Periods covered by the contributing houses illustrate the usual range of rural vernacular building in Connecticut, being predominantly in the Post-Colonial and Greek Revival styles. Two houses are Colonial: 726 Clapboard Hill Road (Samuel Dudley House, c.1738), a one-story cottage originally one room deep with a gable roof, and 212 Clapboard Hill Road (Caleb Dudley III House, c.1764*), a two-story saltbox with lean-to apparently integral, typical of pre-Revolutionary work.

Six houses are Post-Colonial, i.e., built after the Colonial period but still basically Colonial in form. Three of these are the story-and-a-half, two-room deep type that became popular after the Revolution (330 Clapboard Hill Road, Abraham Dudley House, c.1788*; 480 Clapboard Hill Road, Amos Dudley House, 1803; 384 Clapboard Hill Road, Henry Dudley House, 1829). Of these, No. 384 is unusual for this period in that it is a half-house. The remaining three Post-Colonial houses are all two-storied with center chimney and roof ridge parallel to the road in the Colonial manner (764 Clapboard Hill Road, Asher Dudley House, c.1796*; 174 Clapboard Hill Road, John Griswold House, 1806; and 321 East River Road, Hooker Dudley House, 1831). No. 174 Clapboard Hill Road, however, betrays its date in the Federal period with a lowered roof pitch and a main cornice carved with a diamond pattern, and 321 Clapboard Hill Road does the same, albeit very belatedly, with its 4-bay facade and off-center door, a type that first appeared in Guilford around 1805.

There are seven houses of the standard Greek Revival type — temple-front, gable to street with 3-bay facade and off-center door — but with varying detail (167 Clapboard Hill Road, Horace Dudley House, 1836; 333 Clapboard Hill Road, George Dudley House, 1840; 359 Clapboard Hill Road, John Dudley Jr. House, 1840; 465 Clapboard Hill Road, William L. Dudley House, c.1841*; 205 Clapboard Hill Road, Henry Nelson Dudley House, c.1844; 761 Clapboard Hill Road, Horace Dudley Parmelee House, c.1845; 98 Duck Hole Road, Andrew Jackson Dudley House, c.1857). No.167 Clapboard Hill Road, the first of the group to be built, still recalls the Federal style with a half-moon window in the gable. No.359 Clapboard Hill Road is severely plain, 333 Clapboard Hill Road is somewhat less so, being embellished with a simple doorway of the popular Greek Revival type narrow sidelights and surround of Doric pilasters and full entablature. Nos. 205 and 465 Clapboard Hill Road carry this doorway design to a further degree of elaboration. No. 761 Clapboard Hill Road is the most elaborate house of the group, having corner pilasters, a flushboarded pediment, and a large frieze carried around the house. No. 90 Duck Hole Road, not built until the 1850s, is a plain farmhouse perpetuating a late version of Greek Revival form and otherwise without stylistic traits.

Building falls off after this date. There is one house of the 1870s (164 Tanner Marsh Road, H. Francis Dudley House, 1874) that mixes Colonial form with an Italianate cupola and a late Greek Revival door with stilted arch. There is another house in the 1880s (819 Clapboard Hill Road, Henry E. Parmelee House, 1884) not visible from the road, and one in the 1890s (295 Clapboard Hill Road, William A. Dudley House, 1897) mixing Greek Revival and Queen Anne elements. After this there is nothing until c.1912 (Walter Beckwith House), a Bungalow with shingled walls and cobblestone chimney; and then, the whole sequence is brought to a close with three Colonial Revival houses: H. Philip Dudley's (182 Tanner Marsh Road, 1936), and two built by non-Dudleys (15 Duck Hole Road, Frances Flick House, 1928, and 452 Duck Hole Road, Hester Ferris Adams House, 1941).

The Dudleytown Historic District takes its name from Caleb Dudley, who moved out from town to his father's outland sometime not long after 1699 and built a house on Clapboard Hill. Since then eight successive generations of Dudleys have built on the land surrounding the original house, and the Clapboard Hill Dudleys today are the main branch of Guilford's most prolific and enduring family.

Settled in Guilford's early agrarian period and farmed for over 250 years, much of the area today is still cleared and recalls its agricultural past. Two farms are in use for agriculture-related purposes. Many 19th-century barns and small farm buildings remain.

The southern end of the Dudleytown Historic District is on the height of the hill. From here the land slopes northeastward to the wide salt meadows of the river, today in part a plant and wildlife sanctuary of great beauty. Across the river, the road runs into woodland. Strictly speaking, the north end is no longer Dudleytown, for as residents may be quick to point out, "That's Parmelee Town." But Parmelees were married to Dudleys, so today the designation may pass.

Landscape is an important element in giving the Dudleytown Historic District its particular quality, notably the river scenery up and down the valley from the bridge. From East River Road the long undulating roll of fields as they drop down to the river's level is among Guilford's most evocative views of upland and salt meadow, together one of the coastal area's most characteristic historic landscape features.

Nine houses in the Dudleytown Historic District have been built in the last 50 years and are non-contributing. Two of these are set back from the road behind landscaping; most of the rest are not out of keeping with the character of the neighborhood. The group as a whole is well preserved, and the spacing of buildings and fields retains to a considerable extent the old rhythm of farmhouses and surrounding farms. Although most of the farms themselves are gone, fields are cut, many stone walls are intact, and the land is well cared for. Along the northern stretch, a row of old maples gives distinction to the roadside. The road itself, the ribbon that gives continuity to the group as a whole, is an important element of design, with a supple, elegant curve as it dips down to the river and up again, its swift movement stopped for one brief moment by the accent mark of the small, neat bridge. Everything here is well-scaled, both the natural and the man-made environment.

The Dudley Houses: Tabulation

From c.1700 to World War II, in the area presently designated as the Dudleytown Historic District, 22 houses were built by the descendants of Caleb Dudley. Of these, 19 remain today.

Of the 19 that remain today, 6 are still owned by descendants of Caleb Dudley (167, 295, 330, and 359 Clapboard Hill Road; 164 and 182 Tanner Marsh Road).

Since World War II, 5 more houses have been built in the Dudleytown Historic District by descendants of Caleb Dudley (527 and 651 Clapboard Hill Road; 142, 169 and 189 Tanner Marsh Road).

Total number of houses in the Dudleytown Historic District today is 32. Of these, 24 were built by Dudley descendants. Of the 24, 11 are still owned by Dudley descendants.



Criterion A (History). The Dudleytown Historic District is significant as: 1) an unusually complete illustration of a settlement pattern in early Colonial Connecticut and of the subsequent expansion and consolidation of family land holdings and their retention through hereditary chains; 2) a documentation of the growth of a farming community up to the middle of the 19th century, followed by the decline of farming and the eventual conversion of the land from agriculture to residential real estate and conservation; 3) an illustration of the shift in farm ownership from Yankee to immigrant that can be observed in other Connecticut towns around the turn of the 20th century and of the later immigration of middle class people from New York and Connecticut cities beginning in the 1920s.

Criterion C (Architecture). The Dudleytown Historic District is an illustration of: 1) farmhouse architecture from the mid-18th century to the end of the 19th century, showing in particular the plainness of the rural vernacular in comparison with town architecture of the same period and region, and the time lag in the acceptance of new styles; 2) the restoration and preservation movement that began after World War I in the period of the high Colonial Revival and that gave many Connecticut towns and rural areas the appearance they have today. Dudleytown provides examples of many of the most common practices of the movement; 3) the traditional discipline of the vernacular in placing simple buildings in a landscape in relation to one another and to the public highway, in such a way that they attain aesthetic value. The importance of landscape and the roadside as the context of architecture is made plain,

Historical Background

William Dudley, a planter of the original colony, came from England to Guilford in 1639. He was evidently a man of some substance, for in the list of planters in 1645, which it may be assumed was drawn up in order of precedence as was customary, his name is the eleventh, and he was allotted a sizable homelot in town in a desirable location near the West River. Where his outlands lay is not known, as land records were not kept until after the first division had been completed, but by the time of his death in 1683-84 he had acquired, whether by grant or purchase, a large number of scattered parcels, among which the inventory of his estate lists 11-1/2 acres of meadow and 21 acres of adjoining upland "at East River." This would appear to be the seed of the future Dudley enclave on Clapboard Hill.

William Dudley left all his land and "housings" to his son Joseph, and Joseph in turn left the homelot to his son, Joseph II, save only one corner, and divided his extensive and widely dispersed outlands among his many sons. To his second son, Caleb, he left "all my land at East River, both upland and meadow," plus "4 rods of land out of my home lot by the street." To his sons William and Benjamin he also left four rods of the homelot, and these three pieces, lying side by side and fronting on the street, together constituted the "corner" withheld from Joseph. They are one of the most interesting parts of the will in that they may be an indication that at this date (which is sometime before 1712, when Joseph died) the outlying country was not yet so settled that it could be assumed an heir would go straight off to live on it. They are evidently providing an option to continue living in town, going out to the fields by day (or seasonally, staying in a temporary shelter or maintaining servants to do so). At what exact date Caleb actually made the move is not known. Family tradition says 1699, which is the year of his marriage, but this is not documented. In any event, whether then or not long after, Caleb built a house on the river side of Clapboard Hill, near what is now the corner of Clapboard Hill and East River Roads. His father had apparently already started work on the land, or at any rate was using the salt meadows for grazing and the forest for lumbering, for the will speaks of a fence and a sawmill, but there is no mention of a habitation or structure of any sort.

Town records and Dudley wills and inventories give glimpses of the social and economic level of the family at this time. Caleb's father, Joseph I, had been a farmer and a cooper and had served at various times as representative to the General Court and as Town Clerk, both positions of importance. Caleb's brother, Joseph, was a farmer and a blacksmith and died possessed of such luxuries as a dozen books on a variety of subjects and two silver buckles. His brother Benjamin owned two bibles and twelve "small books." Brother Joshua was a farmer who owned a black coat, a beaver hat, a great coat, and a silk handkerchief. All told the picture seems to be that of a respectable and literate family, well-to-do but not on the social level of landowners who did not "work with their hands," this being the great divide between an ordinary citizen and a gentleman.

Caleb, like his father, was a farmer and a cooper. The house that he built is gone now (although it lasted until 1953), but it was probably a good house for its time. Its location could have been seen even then to be strategic. The soil was exceptionally fertile (so Guilford historian Bernard Steiner reports), and the great salt meadows of the river valley provided ready-made land for grazing and haying. Marshland today is taken for granted, but in the early years before the upland had been cleared, it was these meadows that probably constituted the principal asset of the property. The inventory of William Dudley's estate makes this plain: 11-1/2 acres of meadow are valued at t38, while 21 acres of upland are valued at only t20.

In addition to the meadows, there was the river itself, which bordered the property and which not only provided an abundant supply of marine life (fish for eating, salting, and fertilizer; shells for making lime) but access to Long Island Sound and the sea lanes to the outside world, a fact which the first colonists knew well would be of importance as soon as their farms could begin producing produce for export. And finally, in addition to all these advantages of Caleb Dudley's site, Clapboard Hill was the lowest point downstream at which by the end of the 17th century it had been possible to bridge the river. The first bridge, called Hewlett's Bridge then as it is now, was built not long before Caleb's house (Steiner gives two possible dates, 1692 and 1699), and it may have been a factor in Caleb's decision to move, for with the new bridge, the road outside his door became a link in the stage route between New York and Boston and must have facilitated access from town to his cooper's shop.

Caleb bequeathed the farm to his son Caleb II. From Caleb II it went to his son Nathaniel and from Nathaniel to his son John and from John to his son John Jr., who built a new house on the homelot and turned the old house into a farm building, which purpose it served for another century until it was finally demolished in 1953. Caleb's other three sons each acquired farms of their own, Samuel and Noah crossing the river and establishing a Dudley bridgehead on the far side with two adjoining farms having a long combined frontage on the road. Samuel's house is still standing (726 Clapboard Hill Road) but Noah's is gone. Thomas went still farther, up Podunk Road. His house, though much rebuilt, still stands at 531 Podunk, beyond the border of the Dudleytown Historic District.

In the next generation, Caleb II's son Nathaniel, as has been seen, acquired the home farm, and Amos, the youngest son, acquired his Uncle Noah's. Caleb II's other two sons, Caleb III and Abraham, repeated the performance of Samuel and Noah and, moving in the opposite direction (though at different times), again established two adjoining farms with a long combined frontage on the road. Both houses are extant (212 and 330 Clapboard Hill Road), and both, with their generous proportions, speak of the new level of amenity that begins to be observable in Connecticut, first in the years following the French and Indian Wars and then after the Revolution.

In addition to amenity, there is visibly an increasing density of development. By the time the Constitution of the United States is ratified, Caleb I, three of his four sons, and three of his grandsons have raised seven houses in the Clapboard Hill area. In the next generation come four more. No outsiders' houses are interspersed between the Dudleys, and it is probably about this time, or possibly in the next generation, that the name Dudleytown begins to be used. It is given official standing on the Irvine map of Guilford published in 1852, where it is written "Dudley's Town."

All this activity mirrors the general economic expansion of the new nation and, on Clapboard Hill, the major shift to a market economy, in which several factors are combined: the growth of New Haven, New York, and other towns and cities the length of the Atlantic coast, creating an expanding market; the growth of Guilford's shipping facilities and participation in the coasting trade; and the increased productivity of the farms themselves as more land is brought under cultivation. Sometime before the Revolution a road called simply "the lane," now East River Road, had been run down the west side of the river to a spot where a small node of wharves and sea captains' houses was beginning to develop. By 1810 a new bridge across the river had been built here, the lane had been extended to connect with a road running parallel to the shore, and this road in turn became part of the great United States mail route, the Boston Post Road. A shipyard was built, taverns were opened and also boarding houses for shipyard workers, and a new wharf was constructed. This settlement became the port for Clapboard Hill and up-river farmers, the river coming to be known in common parlance as "the farmers' highway." Many years later, in an interview in 1914 preserved in the Guilford Free Library, an old sea captain, Philo Blatchley, provided a glimpse of the interaction of port and farm: "I can remember," he reminisced, "when there was six vessels run from here... I have loaded my [whole] sloop from one farmer. I used to keep John Griswold posted[1], and after I got through going, John used to come and ask me what he had better do about selling. I always told him when I thought it would be a good time to sell."

Information about the crops produced is scant, for Guilford historians have been surprisingly uninterested in discussing agriculture, the town's main support for all its early life. But it is probably safe to assume that Clapboard Hill is similar in this respect to other parts of town of similar terrain where, in the first years, wheat and oats are staples and there are short-lived experiments with tobacco and flax. By Philo Blatchley's day, around the mid-century, Dudleytown is producing hay, beef (salted), potatoes, onions, and turnips — non-perishables not requiring refrigeration like oysters, which were also extensively shipped out of Guilford but not by Dudleytown farmers. Hay was an important commodity, probably reflecting the growing urban density of nearby cities such as New Haven and Middletown, with their increasing number of horses to feed and bed down, and here the full value of the tidal meadows of the river valley with their dense mat of grass (soartina patens) was realized. Self-supporting, self-renewing, needing no fertilizer, weeding, or plowing, the meadows were among the farmer's most valuable assets, as William Dudley had known back in 1683. In the 1960s Paul Dudley, last of the full-time Dudley farmers and owner of Hill Crest Farm, described haying in the old days in an interview with Joel Helander, which Helander has written up in volume II of Guilford Long Ago and which is digested here:

"Every summer it was customary for the Clapboard Hill farmers to mow their salt meadows. A team of horses or oxen pulled the mowing machine over the flats at low tide. Heavy wooden clogs, fastened to each hoof, prevented the animals from sinking in the muck. Yet still, you can guess, it would happen! A great deal of effort was required to free them. Fred Davis points out that "horses go where tractors don't. They have brains and will step over ditches and go around holes." Paul Dudley says that his father was one of the first farmers in the area to use a mowing machine harnessed to the horses; until then, the marshes were cut by hand with scythes.[2]

The Clapboard Hill farmers had a sluice or tidegate to use at haying time, down the river by Cooke's Point you can still see the piles of stones. It kept the water from rising in the flats at high tide, allowing time for the hay to be cut, dried, and pitched onto the hay wagons. The tidegate consisted of one large hewn timber with a gate at each end and a double gate in the middle which automatically closed when the tide came in and opened when it started out. Each fall the farmers worked together and helped remove the gates for the winter. The heavy timbers were stacked in the field at Cooke's Point. In the 1930s a storm tide swept them out and they were never rebuilt."

Today the stones can still be seen at Cooke's Point, and two splendid photographs in the Guilford Free Library show the tidegate in operation and Fred Davis with his team, pitching hay. (Davis owned meadow down-river of the Dudleys and a farm on the Post Road, now Sunrise Development.)

After the generation of Caleb I's grandsons, the lines branched out, and the establishment of new households speeded up. Land records and probate records have not been systematically published, and it is not possible to know precisely how land for new farms was acquired whether new increments are bought by fathers for sons or farms are subdivided for them or whether sons buy land for themselves but such information as is available suggests all three practices. For example, c.1845 Hooker Dudley of East River Road bought 62 acres on Duck Hole Road apparently for the purpose of conveying them to his son Andrew J. (90 Duck Hole Road) when he should get married, which he did in 1857; this land obviously was not part of Hooker's own farm. On the other hand, the deed of Abraham Dudley (330 Clapboard Hill Road) in 1828 conveys to Henry (384 Clapboard Hill Road) "84 rods near Hewlett Bridge being part of my homelot," and in 1844 Asher Dudley conveys 25 acres and his house to his grandson, Horace Dudley Parmelee (761 Clapboard Hill Road). In other cases (Thomas Dudley's, for example) it appears that the son may have bought the land for himself.

In general what stands out in early Dudley conveyances is the transmission of the homelot, undivided, through inheritance by a male heir for many generations (in one of the few cases where a homelot was divided — Amos Dudley's bequeathal of his homelot to his five children — four of the children immediately sold their shares to the fifth). Consciously or unconsciously, a long-term tribal strategy seems to be at work: to consolidate the Dudley holdings into an unbroken land mass on both banks of the river and both sides of the road, and then to hold onto it. By the time of the Revolution the general scheme is in place. In the prosperous years that follow, lines are extended, and at the two extreme ends, to the south and the north, forces are joined by marriage with the Griswolds and the Parmelees: Hannah, daughter of Caleb III, married John Griswold in 1790, and Maria, daughter of Asher, married Jonathan Parmelee in 1819.

An article by John J. Waters, "Family, Inheritance, and Migration in Colonial New England: the Evidence from Guilford, Connecticut," analyzes the process of land acquisition in stem families, emphasizing the role of inheritance by a chain of male heirs (usually eldest sons) in holding land together and expanding it with additional increments acquired for younger sons by purchase or the arrangement of advantageous marriages. In discussing continuity over the generations, Waters also emphasizes intra-family marriages and intra-family sales, for both of which the Dudleys provide examples. In 1796 Asher, son of Samuel, married Lucy, daughter of Abraham; and, illustrating a form of double intra-family marriage that Waters mentions particularly, in 1837 Horace married Hannah Amanda, daughter of Timothy, and in 1840 his brother John Jr. married Hannah Amanda's sister Sarah. Intra-family sales are evidenced by the purchase in 1822 by Joel, son of Abraham, of the Caleb III house (212 Clapboard Hill Road) after the death of Caleb's son; also by the purchase in 1869 of Amos's house (480 Clapboard Hill Road) by Eli, and again by Eli's later purchase of George's house (333 Clapboard Hill Road). Eli bought one more Dudley house, Henry's (384 Clapboard Hill Road), in 1904. Waters' article makes no mention of the Dudleys (it is focused entirely on East Guilford, which is now Madison), but the Dudleys provide an extraordinarily apt illustration of his thesis, both in family records and along the roads of Dudleytown today.

Waters' study goes only to the Revolution, but the process continues. The momentum builds up, reaching a peak in the antebellum period when eight new houses are built between 1831 and 1857. Building abruptly falls off around the time of the Civil War. Although Dudley farms continue to coast on a respectable economic level, growth stops.

Starting in the latter part of the century, signs of change occur which in various ways seem to reflect the mounting problems besetting New England agriculture as the fertile lands of the West draw off its manpower, as the development of the railroad brings the competing produce of western farms into eastern markets, and as the industrial cities of the east hold out prospects of easier and more remunerative work. Some of the ways in which these large events affected a small Connecticut community can be sensed from a study of Dudley family trees and chains of title. Five things stand out:

1. A decline in the number of sons staying on the land, and the termination of family lines with an unmarried daughter. In the early 1890s, four Dudley houses were owned and lived in by aging, single women: Kate and Harriet in the Henry Nelson Dudley house, Emily in the Caleb III house, Fanny in John Jr.'s house, and Mary Ann in Samuel's house.

2. The sale of farms out of the family. From the time when William Dudley, the planter, acquired the first lot on Clapboard Hill (sometime before 1650 seems a probable date), for over 200 years no Dudley land on the Hill was sold except to a Dudley nephew or cousin, but shortly before the Civil War sales began. In 1857 William L. Dudley sold out and went west to Wisconsin; in 1862 Henry died, and his only son sold the farm; and in 1870 Andrew J. Dudley sold out and moved to New Haven. In all three cases, the tenure of the new owners turned out to be unsettled. In the next 40 years, three owners successively owned Henry's property, and by 1919, nine had owned William L. Dudley's. Andrew J. Dudley's farm fared little better (as the last farm to have been established in Dudleytown, it may have been the least desirable). The first buyer, probably either a mortgage holder or speculator, immediately turned it over, the next held it for only eight years, the next for ten, and finally it was sold to a team of circus impresarios from San Francisco who used it seasonally as training quarters (one of their protege's acquired fame as the first to turn three somersaults over the back of an elephant, a feat which got him a job with Barnum and Bailey).

A pause of 25 years followed Andrew's move to New Haven, then another sale occurred in 1894 (Caleb III), another in 1911 (Hooker), and two in 1920 (H. Nelson Dudley and Samuel), two of which experienced the same troubled series of turnovers as the previous ones. Only Nelson Burr, a farmer from Killingworth who bought the Caleb III house and whose daughter and son-in-law later bought the H. Nelson Dudley House across the street, where his granddaughter still lives, is an exception, maintaining the traditional Dudleytown pattern of continuity through generations.

3. Use of houses for rental income. Among the complicated turnovers in the chains of title that can be observed in these years, many names of short-term out-of-town buyers can probably be taken as indicating the presence of real estate operators using the houses for speculation and interim rental income. In at least one case this is well documented, that of the William L. Dudley House, which seems to have been turned into a rural tenement for a while, and occasional oblique remarks by later owners of other houses suggest that at the time of acquisition there were signs of similar use and lack of maintenance. Among the Dudleys themselves, a fair amount of house-renting occurred: Eli Dudley, at different times, owned and rented out the Amos Dudley and Henry Dudley houses, William A. Dudley rented out the George Dudley House, and Henry E. Parmelee variously rented the Samuel Dudley House or used it for storage. The Horace Dudley Parmelee House may perhaps have been either rented or vacant during the 1920s. Horace C. Dudley (the second Horace Dudley) rented his own house and went to live in his father's house after his wife died.

Unfortunately there is little information about the tenants, but later chance remarks indicate the presence of a number of immigrants and imply that few (or perhaps even none) were serious or successful farmers but were employed part-time doing odd jobs in the neighborhood or working in town. At least one is known to have been employed in a Branford factory, an indication probably of the effect that the interurban trolley, which came through from New Haven to Saybrook in 1911, was having on rural life.

4. Immigrant buyers. In this period numerous ethnic organizations in New York and elsewhere were promoting the settlement of immigrants from rural Europe in Connecticut, where, as market value declined, farms were cheap. Dudleytown provides at least one full-fledged example of this movement, the William L. Dudley House; and two Dudley houses on the border of the district on Podunk Road (the Thomas Dudley and Samuel Cruttenden houses) add two more. Between them, the names of their buyers show a wide range of ethnic backgrounds: Gustav Heymann, David Cohen, Alexander Ulatowsky, Peter Stachac, Hugo Schulz, Louis Kessler, Arthur Rosch, Joseph Perrone, Isadore Lisensky, among others. Like the rental tenants, few of these people lasted long or seem to have been successful as farmers, and in many cases rapid-fire turnovers suggest mortgage foreclosures. Only one person stayed more than a few years, Theodore Tetzlaff, who bought Hooker Dudley's farm in 1911 and lived there until his death in 1969. The experience (recounted by Helander in Guilford Long Ago) of Theodore's brother, Herman, who bought a farm on Tanner Marsh Road adjoining the Dudleys, may have been more usual. "My father's farming endeavor," his son said many years later, "was a tragic failure."

From the point of view of the Yankee farmer, the whole situation was wryly summed up in a letter to the Shore Line Times in 1918, quoted by Linda Baxter, which was written by a former farmer from Guilford who had moved to Hartford: "The Yankee farmer, he said, 'was a trifle more than self-supporting; he educated his children after a fashion, paid his taxes, and at the end of this career had a decent funeral after which his children sold the place to someone whose name ended in "ti" or "owski" and beat it to the city.'"

5. City folk and the Depression. The 1920s brought a dramatic change, startling in its swiftness, which saw the replacement of the immigrant farmers by a new wave of immigration, this time consisting of people from the urban middle class. The real estate record is decisive. Until 1930, Dudley farms had gone out of the family on the average of fewer than one a decade. In the single decade of the 1930s, five went out of the family (333, 359, 384, 480 and 761 Clapboard Hill Road). All five were bought by city people for use as weekend and summer homes. At roughly the same time, re-sales of four more Dudley houses went to people of the same sort.

The Depression may have been a factor in triggering all this, causing Dudley farms to be given up, also causing the collapse of the ethnic settlements, and at the same time creating a psychological climate in which people who still had moderate means began to search for places in which to lead simple and inexpensive lives. Other factors, as Mary Hoadley Griswold astutely pointed out in 1928 in an article in the Shore Line Times about the new settlers on Clapboard Hill, were the automobile, the increasing paving of roads, and rural electrification. Finally the full impact of the Colonial Revival should probably also be included, with its creation of a romantic image of the New England village and rural landscape, tempting people out into the country to buy Colonial houses and American antiques.

The urbanites were at first mostly summer people. The Connecticut Turnpike had not yet been built, and until the 1960s Guilford was thought to be "far away." Dudleytown attracted an interesting group, mostly from the professions and the arts (the most eminent was Aldous Huxley, who spent one summer in the Samuel Dudley House), and with the great natural beauty of its landscape and its unspoiled houses, it also attracted another type of buyer who, in many parts of the state in this period, played a role in the development of modern rural Connecticut, namely, the long-term investor turned country gentleman, who could afford to buy up blocks of old farms on a large scale and hold them through more than one generation. Starting in the 1920s, two men of wealth, John Orcutt, a New York banker, and Franklin Parrel, a manufacturer from Ansonia (followed by his daughter and son-in-law, Estelle and George Goss), acquired hundreds of acres, the Gosses' land running up the East River valley, in and beyond the Dudleytown Historic District, and Orcutt's adjoining the district along Podunk Road and Murray Lane. Today the Goss holdings amount to some 500 acres, mostly still open. Orcutt's land is now filling up with development.

Taken all together, these developments suggest a picture of a community in a time of upheaval and transition from the old agrarian life to something new. Farming perceptibly changes in this period. Although one still hears of onions, potatoes, and turnips, dairying became more important, both in the form of two sizable commercial dairies (Hill Crest Farm and Maple Shade) and of small farmers selling to the dairies or in some cases peddling their milk along the road. Chicken farming also became important, while up at the north end of the road the Parmelees switched to lumbering, a business having been started by Henry E. Parmelee shortly after the Civil War. Timber was cut on the many Parmelee woodlots, and a sawmill was built on a stream emptying into the East River, approachable from Duck Hole Road.

At the other end of town, the Dudley men also were changing their way of life. More of them now had higher education experiences, more were going to work in New Haven or neighboring towns: William A. Dudley for example, with a job at Yale University, carried eggs into New Haven with him in the morning, in a suitcase. Others gave up farming altogether, or pursued it part-time, supplemented by other employment.

By World War II, with these far-reaching changes in the population and economy of Dudleytown — with country people working in the city, and city people living in the country the creation of a modern suburb had begun, and with the coming of the Connecticut Turnpike in 1958 and the shift of the urbanites from summer people to year-rounders, the conversion of the land from agriculture to residential real estate became virtually complete. Maple Shade Dairy was given up in 1951, and when, in 1967, Vernon Dudley put his herd up for auction and closed Hill Crest Farm, a large crowd of townspeople turned out to watch the sale, and many could be heard saying, "It's the end of an era."

Criterion C, Architecture

Dudleytown's houses, when seen in chronological order, provide a remarkably complete sample of the history of a rural building culture in a Connecticut farm community. The period of initial construction is roughly from the mid-18th century to the time of the Civil War, an era of agricultural growth and prosperity in Connecticut and much of New England, and while in a general way the Dudleytown houses reflect the successive fashions that are familiar from textbooks of architectural history, they also underline the conservatism of the country builder. New styles come slowly, and when they do, they tend to take the form of details, while traditional shapes and configurations hang on. For example, the Caleb III house of c.1764* (212 Clapboard Hill Road), insofar as its original form can now be judged, appears little different from houses that were being built in town from the 1730s or 1740s on; and in the Federal period, when the town is blooming with two-chimney, center-hall plans and subsequently with the innovative 4-bay plan with off-center door, Dudleytown clings to the old center chimney (for example, 174 and 764 Clapboard Hill Road). Even John Griswold, (174 Clapboard Hill Road), who went so far as to have an expensive frieze on his main cornice in the manner of Asher Benjamin, still held to the center chimney; and although Hooker Dudley (321 East River Road) in 1831 broke with tradition and adopted the 4-bay plan, it was about 25 years after it had first appeared in town.

A change comes in the antebellum period, briefly but vividly. The Greek Revival marks Dudleytown's moment of glory, and the Dudleys swiftly caught up with the new style. This is the only period for which the name of a builder-architect is recorded — George Bushnell, a Dudley cousin who had married Eunice, daughter of Nathaniel. He lived in Winthrop, 15 miles away, and he came to Dudleytown in 1836 to build the Horace Dudley House (167 Clapboard Hill Road). He walked from Winthrop, boarded during the week, and walked home on Saturdays in order to be back on time for church; he charged $190.00. Although the house he built still shows Federal influence, it has Dudleytown's first gable front and Doric doorway, that widespread earmark of the new style. Other houses have been attributed to Bushnell, although not all the attributions can be definitely pinned down; namely, the John Jr., H. Nelson Dudley, and possibly George Dudley houses (359, 205 and 333 Clapboard Hill Road). The Henry Nelson Dudley and George Dudley houses, as well as the William L. Dudley house (465 Clapboard Hill Road) and the Horace Dudley Parmelee House (761 Clapboard Hill Road) are all mature examples of the Greek Revival, comparable to work being done in town at the same time. Caleb III's old house also should be mentioned, for it too did its part in keeping the Hill up to the minute by following the current vogue in town for putting a Greek Revival doorway on a Colonial facade, this being one of Guilford's most characteristic features then and still today.

After this flowering, construction falls off, and styles become less pure. The H. Francis Dudley House of 1874, although impressive by its size and flamboyant cupola (which occasioned much comment on the Hill, as Mary Jane Dudley reports in a letter quoted in Helander's "Dossiers"), is an uninhibited mixture of stylistic traits (164 Tanner Marsh Road), and the William A. Dudley House of 1897 (295 Clapboard Hill Road) presents a front to the street that could be taken for a standard design of the late Greek Revival vernacular of 30 years before, with Queen Ann additions. Only the Beckwith Bungalow of c.1912, possibly from a mail order plan or builder's catalogue, and the Colonial Revival houses built after World War I (15 Duck Hole Road, 452 East River Road, 182 Tanner Marsh Road), at least 2 of them designed by professional architects, obviously reveal their dates.

Except for their doorways, Dudleytown houses tend to be plain, and this too, like their conservatism, is a common trait of rural building. Even in the heyday of the Greek Revival, such familiar sights on town streets as a flushboarded facade or an entry porch supported on a pair of Doric columns are absent on Clapboard Hill. In particular, one notes a contrast between the Hill and the maritime boom town down the river by the new bridge and shipyard, where two or three richly pilastered recessed doorways could be seen and where the owner of the shipyard had a frieze with triglyphs on his porch (58 East River Road and 32 Boston Post Road). By contrast, the Horace Dudley Pannelee house in Dudleytown (761 Clapboard Hill Road), while stylish and probably costly, with flushboarding in the pediment and robust pilasters on all four corners, preserves the scale and texture and compact outline of tradition and does not stand out from its neighbors. It underscores the fact that the architecture of Dudleytown is an architecture of community rather than of novelty and individual display.

The nearest approach to pretentiousness comes toward the end of the century with the Henry E. Parmelee House (819 Clapboard Hill Road). Built in 1884, the Parmelee house is the grand climax of the whole development on Clapboard Hill, but on analysis it is not so much that the house itself is grand as the way in which it is presented. It is set imposingly on a hill well back from the road, with a long lawn in front and a long driveway, while the farm buildings are segregated across the street. Although not elaborate, the whole layout speaks the language of one of Downing's "rural residences" rather than that of the farmhouses of Currier and Ives.

After the Parmelee house there is only one other new Dudley house until 1936 — a 50-year period of retrenchment and economic change on Clapboard Hill. Little is recorded about what happened to the houses during that time, but the fact that so few Queen Anne or Classical Revival porches were ever built and so few side wings were added suggests a community that was at a standstill. A few later reminiscences by the new urban arrivals indicate that some of the houses that had been used for rent or fast sales were in poor shape (Eleanor Little, for example, in "Old Scrogie" tells of fallen ceilings in the Samuel Dudley House), but for the most part everything seems, amazingly, to have stayed just the way it always had been.

Change came in the 1920s and 1930s with the high Colonial Revival and its emphasis on restoration, which by this time was becoming a widespread movement, popularized by an increasing number of exhibits of period rooms in museums and historical societies and by a flood of books, magazines, calendars, and other publications by such well-known photographers, writers, and architects as Wallace Nutting, Samuel Chamberlain, J. Frederick Kelly, and Elmer Keith, architectural editor of the Federal Writers' guide book for Connecticut. On the exterior, not much changed in Dudleytown, but most interiors were modernized (bathrooms, closets, electricity, kitchen appliances) and many at the same time were "restored," the style simultaneously moving forward to the 20th century and backward to the 18th and in either case away from the 19th.

Three of the new owners, Anne Conover (of the William L. Dudley House, 465 Clapboard Hill Road), Eleanor Little (of the Samuel Dudley House, 726 Clapboard Hill Road), and Georgia Newcomb (of the Amos Dudley House, 480 Clapboard Hill Road), have left accounts, either written or oral, of the changes they made, and they provide good examples of the taste and practices of the Colonial Revival. Fireplace openings that had been closed for stoves were opened full width, Victorian mantels were removed to show bare lintels, ceilings were removed to expose joists, casings were removed to expose corner posts and summer beams, paint was stripped, woodwork was sanded, old barns and sheds were torn down to provide floor boards and timbers for new additions. Corner cupboards and hardware were found in country antique shops. Paneling or wainscot was bought from dealers in salvaged materials (this type of acquisition, as described by Georgia Newcomb, involving treasure hunts around the state over a period of years), and if the real thing was not obtainable, skilled artisans ("local workmen trained in old fashioned methods") were employed to reproduce it. Examples of all these well-known practices appear in the three ladies' accounts, and they are supplemented by accounts of even more ambitious programs by John Orcutt in the Thomas Dudley House on Podunk Road on the border of the Dudleytown Historic District and, climactically, in George Goss's work on the Andrew Jackson Dudley Farm (90 Duck Hole Road), which he and his wife Estelle acquired from her father in 1927. Goss preserved the farm buildings at the entrance to the property, which he named Duck Holes Farm, installed a German caretaker-farmer in the house, and then chose a dramatic new site for the main residence on empty land some distance up the river at the head of the view down the valley. (The site is beyond the northern border of the present Dudleytown Historic District. To this site he moved an 18th century saltbox, the Ebenezer Scranton House from North Guilford. Architect for the restoration was J. Frederick Kelly, and no pains were spared to do the job well.

House Beautiful had an article about the Goss restoration in September 1939, which began by exclaiming, "Here is the real New England," and went on to say, "Many of us are buying deserted farms and rehabilitating them as dwellings. Here, in one house, is an ideal handbook to set up as a model of patience and taste." The author characterized the finished building with three perceptive adjectives which say much about the ideals of the Colonial Revival: "aristocratic, beautiful, and sensible."

To House Beautiful's account, Eleanor Little later added the further note that Goss bought two more houses, which were about to be flooded by a new reservoir in Branford, and demolished them for spare parts, some of which he gave to her for her own house (Samuel Dudley House, 726 Clapboard Hill Road); some also he gave to the Newcombs for the Amos Dudley House (480 Clapboard Hill Road).

This too — this grafting of tissue from one house to another was one of the familiar practices of the Colonial Revival and shows the reverse side of the restoration movement. By the 1920s it had become widespread enough in the declining farm areas of Connecticut to attract notice in local newspapers. The Shore Line Times in Guilford wrote in 1928:

"Herbert E. Jones and Sons of Guilford are in the midst of a contract to take down and store for Frank J. Foster, an architect of New York, a number of old houses and barns... Already the truck has taken one order of the old material to Great Neck, L.I....

Once upon a time these buildings would have been sent to the woodpile... Now the handicraft of the forefathers has value as something which will never again be produced so prodigally. Modern architecture sends out a call for aged frame timbers, flooring, fireplaces..."

In Dudleytown, the owner of the John Dudley Jr. House (359 Clapboard Hill Road), in whose back yard the derelict ancestral Dudley homestead (Caleb I, c.1700) still stood, provided a typical example of this practice, demolishing the building in 1953 and selling or giving its timbers and flooring to a man building a "Colonial" addition to his house in Guilford.

In addition to inspiring restorations, the Colonial Revival also brought a final spurt of new construction to Dudleytown — three new houses were built between 1928 and 1941. Two were for newcomers: Frances Flick on 15 Duck Hole Road (1928) and Hester Ferris Adams on 452 East River Road (1941). One Dudley, H. Philip, built a new house as well — next to his grandfather's on 182 Tanner Marsh Road (1936). All three are Colonial Revival in style, and architects' names are recorded for two of them, the first known work by professional architects in Dudleytown. Philip Dudley's house was designed by Charles Scranton Palmer of New Haven, and the Adams house by Robert H. Schutz of Hartford.

At the same time that these developments were taking place, the Dudleys who had remained on Clapboard Hill were making comparable changes affecting the architecture and landscape of Dudleytown, modernizing their houses, removing old farm buildings, and converting trampled barnyards to lawn (Helander describes the alteration of the Horace Dudley grounds in Volume I of Guilford Long Ago, on page 18). In 1932 the road was paved (according to Eleanor Little, done at the urging of John Orcutt in order to make his undeveloped Podunk land more accessible to people from town), and in 1948 Hewlett's Bridge was rebuilt with the present stone-faced arch and stone deck posts, the town having given considerable attention to the quality of design and material.

By World War II, which is the end of the period covered by this nomination, a new image had come to fruition on Clapboard Hill an image that is a fully-realized example of the aesthetic of the Colonial Revival. Houses were painted white (as they always had been, old timers assert), fences stood in front of many of them, and all but a few still retained their shutters. Unity of color, fence lines, and strongly patterned facades of dark-green-on-white linked the buildings together and established continuity along the road, giving the group as a whole an identity. The importance of landscape as the sustainer of architecture was and today still is made plain, for while the individual buildings are not unusual, the unfolding progression of simple, handsome houses, bound together by a country road and surrounding open fields and wetlands creates a sense of time and place that is outstanding.


  1. John Griswold's house is 174 Clapboard Hill Road, until 1988 still owned by a John Griswold.
  2. Paul Dudley's father was H. Francis Dudley. Born in 1846, he was actively involved in the farm from about 1860 on. Although Paul himself belongs to the 20th century, the things he describes had probably changed little from earlier times.

*Unverified; a reasonable estimate.


All the data given in this nomination about the owners, dates, and conveyances of Dudley houses is from Joel E. Helander's Guilford Long Ago and his "House-Dating Dossiers." Without his careful research and his generous help this nomination could not have been written.


Baxter, Linda Trowbridge. The Newcomers; A Study of Immigrants to Guilford, Connecticut, 1850-1930. Guilford, Connecticut privately printed, 1985.

Beers, J. H. & Co. Commemorative Biographical Record of New Haven County. n.p., 1902.

Blatchley, Philo. Interview by Charles Hubbard, 1914. Copy in Guilford Free Library.

"Duck Holes." New Haven Register, August 12, 1934. Article about George Goss house.

Dudley, Dean. History of the Dudley Family with Genealogical Tables, Pedigrees & c. Wakefield, Massachusetts: published by Dean Dudley, 1888.

Griswold, Mary Hoadley. Yester-Years of Guilford. Guilford, Connecticut, 1938.

Guilford Preservation Alliance. Survey of the Historic Architecture of Guilford, Connecticut, 1981-82. Produced under a grant from the Connecticut Historical Commission. Typescript, 3 volumes, in Guilford Free Library.

Helander, Joel E. Guilford Long Ago. 2 volumes. Guilford, Connecticut: privately printed, 1969 and 1970. Copies in Guilford Free Library.

________"House-Dating Dossiers." Typescript, 1970-. Copies in Guilford Free Library.

Little, Eleanor. "Old Scrogie Clapboard Hill Road Changes in Structure in the Original House." n.d. Typescript in Guilford Free Library. Article about Samuel Dudley house.

"New England Heritage." House Beautiful, September 1939: 24-29. Article about George Goss house at Duck Holes Farm.

Steiner, Bernard. History of Guilford and Madison, Connecticut, 1897, reissued 1975, Guilford Free Library, Guilford, Connecticut. This book is based on a manuscript written c.1840 by the author's grandfather.

Waters, John J. "Family, Migration, and Inheritance in Colonial New England: The Evidence from Guilford, Connecticut." William and Mary Quarterly. 3rd, series, 39 (January, 1982).


Conducted by Elizabeth Mills Brown, 1985-1986.

Anne Conover; H. Philip Dudley; Ralph Dudley; Eleanor Little; Georgia Newcomb.

Elizabeth Mills Brown and Christopher Wigren, architectural historians, and John F. A. Herzan, Connecticut Historical Commission, Dudleytown Historic District, Guilford, New Haven County, Connecticut, nomination document, 1991, National Park Service, National Register of Historic Places, Washington, D.C.

Nearby Neighborhoods

Street Names
Clapboard Hill Road • Duck Hole Road • East River Road