Woodstock Hill Historic District, Woodstock Town, Windham County, Woodstock CT, 06281

Woodstock Hill Historic District

Woodstock Town, Windham County, CT

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The Woodstock Hill Historic District was listed on the National Register of Historic Places in 1999. Portions of the content on this web page were adapted from a copy of the original nomination document. [‡]


The Woodstock Hill Historic District is a town-center village of more than 65 properties extending along Route 169 on a ridge in the south-central section of Woodstock, Connecticut. The settlement has a central north-south spine, formed by Plaine Hill Road and Route 169, from which a number of side streets extend at odd angles; these include Old Hall Road, Roxbury Road, Child Hill Road, Academy Road, and Hill Cemetery Road. The center of the Woodstock Hill Historic District is defined by a small level, open area known as the Woodstock Common, on the east side of Route 169 between the 1821 Congregational meetinghouse and the 1873 Woodstock Academy building. Immediately to the east of the Common is the Woodstock Hill Burial Ground, a small cemetery established in 1686, which contains numerous examples of 18th and 19th-century gravestone carvings. The Woodstock Hill Historic District includes a blend of residential, commercial, agricultural, religious, and public buildings in a wide range of architectural styles, including the vernacular Colonial architecture of the 18th century, the Federal and Greek Revival styles of the early 19th century, the Gothic Revival and Italianate styles of the Victorian era, and early 20th-century styles such as the Colonial Revival. The buildings are generally of frame construction, 1-1/2 or 2-1/2 stories high, with exteriors covered with clapboards, shingles, or siding; there are also a few constructed of brick or stone.

The Woodstock Hill Historic District's oldest buildings, such as the c.1782 Asa Bishop Tavern at 45/47 Academy Road, 1777 John Flynn House at 30 Child Hill Road, and the 1801 house at 486 Route 169 that served as Woodstock's first academy, have the broad-side-to-the-road orientation, symmetrical five-bay facade, and small-pane divided sash typical of colonial Connecticut's domestic architecture. The early 19th-century houses in the Woodstock Hill Historic District exhibit cornice and entry details associated with the Federal or Greek Revival style. The John Napping House at 512 Route 169 has the denticulated cornice, fanlight transom, and pedimented entry characteristic of the Federal style, while the bolder scale of the Greek Revival's Classical details, such as wide corner pilasters and deep cornice moldings, is evident in the Caleb Fenner House at 519 Route 169 and the Hill Church Parsonage, 539 Route 169. Several of the early 19th-century houses have hipped roofs.

Many of the Woodstock Hill Historic District's buildings from the Victorian period are Italianate inspired, with bracketed cornices, bay windows, arched window shapes, and elaborate porch detail, as in the Woodstock Academy classroom building (individually listed on the National Register of Historic Places). Another example of Victorian architecture in the district is the Gothic Revival style Roseland Cottage, 556 Route 169, a small house with steeply pitched gables, decorative vergeboards and finials, pointed-arch windows with diagonal-pane sash, and quatrefoil porch ornamentation. Because of its significance as an exceptional example of the style, it has been designated a National Historic Landmark.

A number of the residential properties have outbuildings that are counted as contributing resources. About two dozen sizeable barns dating from the middle to late 19th century can be found behind the houses.

There are two religious houses of worship within the Woodstock Hill Historic District. On the east side of Route 169, south of the Woodstock Common, is the First Congregational Church of Woodstock, an 1821 white-painted Federal style building with arched entries, a Palladian window, and multi-stage steeple. The second church stands at the northeast corner of Route 169 and Child Hill Road and was originally the Swedish Congregational Church (but now known as the Evangelical Covenant Church). The Victorian period church was built in 1891 to serve the growing Swedish community in Woodstock.

A few buildings now serve commercial purposes, such as the Georgian style, hipped-roof Matthew Bowen Homestead at 94 Plaine Hill Road, now known as the Inn at Woodstock; individually listed on the National Register of Historic Places). There is also an apple barn and orchard at 494 Route 169.

Near the northern boundary of the Woodstock Hill Historic District is the Senexet Grange No. 40, Woodstock Hill's social hall. The small stone building was constructed in 1930 as a gathering place for the agricultural community and remains in use for social events. The small brick Neo-classical style building at 523 Route 169, built in 1916 and known as Palmer Memorial Hall, has served several town functions. The rear of the building was the location for Woodstock's first volunteer fire department until 1958, when the building was renovated to accommodate town meetings. Currently, Palmer Memorial Hall serves as the home of the Woodstock Historical Society.

The Woodstock Hill Historic District's historic buildings are generally well-preserved, with appropriate siding material, sash, and brick or stone chimneys. Not many have been substantially altered, and few buildings are of modern construction.

The boundary of the Woodstock Hill Historic District embraces nearly the same properties as that of the Woodstock Hill local historic district.



The Woodstock Hill Historic District is significant for its historical associations with institutions and people important in the development of the area as a town center; for the architectural qualities of its buildings, many of which represent well-preserved examples of particular periods and styles of architecture; and for the landscape qualities of its common, a small ornamented park that was created by a local philanthropist in the spirit of the village improvement movement. Woodstock Hill was the location of the town's first Congregational church, burying ground, and common. Here were held the religious services, town meetings, and militia-company drills that formed the basis of community life in the 18th and early 19th centuries. Later, other institutions were established in the village on the hill, notably the town's academy, a public library, the Grange hall, and a building for town offices. The Woodstock Hill Historic District also includes numerous historic houses associated with prominent Woodstock families, such as that of Henry Bowen, who was responsible for such civic endeavors as the 1873 Woodstock Academy building and the transformation of part of the common into a small park-like village green. The Woodstock Hill Historic District's many well-preserved dwellings and barns from the 18th and 19th centuries, along with its churches, halls, cemetery, and the Common itself, all combine to make Woodstock Hill a unique village in the northeastern Connecticut countryside.

Historical Significance

The area embraced by the Woodstock Hill Historic District has been the focus of the religious, political, and social life of Woodstock from its earliest years. English settlement of the area that later became the Town of Woodstock began in 1686, when a group of 13 men from Roxbury, Massachusetts, were granted permission by the General Court of Massachusetts Bay Colony to purchase and settle the area then known as Wabbaquasett. These early settlers, known as the "Goers," located their families and farms along the Plaine Hill ridge and named the settlement New Roxbury after their native town. In 1690, the area was renamed and incorporated as the Town of Woodstock. It remained under Massachusetts jurisdiction until 1749, when it was annexed to the Connecticut Colony. At the time of settlement, the townspeople set aside a tract of common land for public purposes, such as the site for a Congregational meetinghouse and a burial ground. Construction of the first meetinghouse was completed in 1691; it was located on the southern end of the Woodstock Common adjacent to the cemetery. In 1719 a second meetinghouse replaced the first structure, which proved too small to accommodate religious services for the growing community. The present meetinghouse, the third, was erected in 1821 on the same site as the original church. In addition to its religious functions, the meetinghouse accommodated town meetings and public elections.

The Woodstock Hill Burying Ground is Woodstock's oldest cemetery. The cemetery includes fine examples of early gravestone carvings from local as well as prominent Newport and Boston carvers. Many of the earliest stones are attributed to John Holmes, Jr., son of one of the original settlers of Woodstock. The earliest marker, dating 1689, belongs to Lieutenant Edward Morris. Among others buried in Woodstock Hill Burying Ground are two members of the Bowen family: Henry Bowen, one of the 13 original settlers, and Henry C. Bowen, a significant benefactor of Woodstock during the mid-19th century.

During the 18th century, Woodstock, like most other Connecticut towns, was a farming community whose families engaged in generalized agriculture. Many of the district's historic houses are accompanied by barns and other agricultural outbuildings, recalling the area's origins as an agricultural community.

By the early 19th century, a few shops and places of entertainment were scattered around the town common. In 1782, Asa Bishop was granted a parcel of land north of the Woodstock Common where he built a tavern, selling out after only two years to William Bowen. Under the Bowen family the building served as a store, cooper's shop, and slaughterhouse, as well as a tavern. In 1801, the Norwich and Woodstock Turnpike, following the route of present-day Route 169, was incorporated, and in 1808, it was joined by the Woodstock and Somers Turnpike. With improvements to both roads, commercial activity at Woodstock Hill picked up, at least for a while. William Kinney Green, an early textile manufacturer, bought the John Bartholomew House in 1820 and operated a tavern there for 14 years. He also ran a small shop south of the Congregational Church.

Woodstock Hill was also the setting for educational institutions. In the early 19th century, many New England towns began to establish secondary schools to continue training beyond district school education. The Reverend Eliphalet Lyman, pastor of the Congregational Church, and attorney John McClellan were both instrumental in establishing an academy at Woodstock Hill. On February 4, 1802, the first Woodstock Academy, a 2-story wood-frame building with two classrooms, one for boys and the other for girls, was opened for session. The private school's early existence was continually plagued by financial constraints and a declining enrollment until 1843, when Henry C. Bowen, a wealthy native and summer resident of Woodstock, donated funds to reinvigorate the school. His contributions to the academy continued until his death. In 1872, the academy's Board of Trustees voted to build a new structure and commissioned Norwich architect Alexander S. Cutler to design the building. The original school was removed to its present site at 486 Route 169 and the following year, the new 3-story Italianate style academy building was dedicated. The school prospered and expanded well into the early 20th century; though still private, it now serves as Woodstock's public high school. Another educational building is the house at 31 Hill Cemetery Road, which once served as a school for girls in the second half of the 19th century.

From the earliest days of English settlement, the Bowen family has held a place of distinction in the Town of Woodstock. The Bowen name was established in Woodstock by Henry Bowen, one of the original "Goers" from Roxbury, Massachusetts, who founded the town. The family continued to be leading figures in political and social matters throughout the following years, residing in the district's most notable houses, such as the National Register listed Matthew Bowen Homestead at 94 Plaine Hill Road and the Colonial Revival style Arthur Sherburne Hardy House at 493 Route 169. Perhaps the most prominent member of the Bowen family was Henry Chandler Bowen (1813-1896), who was born and raised in Woodstock and later proved to be the town's greatest philanthropist. As a young man, he left his hometown to pursue a mercantile career in New York City and soon after founded and published The Independent, a Congregationalist and abolitionist newspaper. While remaining a resident of Brooklyn, New York, he returned to Woodstock in 1846 to build a summer home and named it Roseland Cottage. His return to Woodstock proved to be greatly beneficial to the town; he generously donated money to support expansion of Woodstock Academy and landscaping of the Woodstock Common. His greatest town project was creating the Roseland Park, a place for large community gatherings and activities, located east of Woodstock Hill. It was dedicated on July 4, 1876, in celebration of the nation's Centennial; Bowen set up a trust to manage the property for the benefit of Woodstock residents. Bowen continued to spend his summers at Roseland Cottage and charitably gave to the town until his death in 1896.

Other examples of philanthropy include the generosity of Minnie Palmer Dean, who constructed Palmer Memorial Hall in honor of her father and grandfather in 1916. It was presented to the town in 1925 at the time of her death. The building was the site of town offices and meetings until 1990, when a new town hall building was completed south of the district. In 1924, the family of Howard Webster Bracken ensured the continuance of his memory by donating funds for a library, named in his honor. It was intended to serve both as a public library and as a library for Woodstock Academy.

While neighboring towns prospered from growing industrial enterprises during the late 19th century, Woodstock's economy proved much less robust. Without the waterpower required to sustain large industries such as those in nearby Danielson and Putnam, and bypassed by the area's railroads, Woodstock was not able to export goods to outside markets nor bring in travelers. Except for a half-dozen small and relatively short-lived textile and twine mills, the town failed to develop either industrially or commercially. Instead, the Woodstock Hill area continued to rely on agriculture, including orchard and dairy production, well into the 20th century. The Senexet Grange No. 40, 628 Route 169, was constructed in 1930 by the Woodstock Creamery Association to provide a place for social functions for the town's farmers.

Woodstock's predominantly English heritage was added to in the late 19th century by an influx of Swedish immigrants, the earliest of whom were brought to the United States by the Bowen family to work as farm laborers. Eventually, many of the Swedish families paid off their obligations to the Bowens and were able to purchase their own farms in the area. In the 1870s, the immigrant communities of Woodstock and nearby towns began holding Swedish-language church services in private homes. By 1890, the congregation had become too large for these arrangements, and the town offered it an old shop at the north end of the Woodstock common land for religious services. By the following year, enough money was donated and borrowed to build a church for the Swedish congregation, added to over the years and now known as the Evangelical Covenant Church.

Architectural Significance

Woodstock Hill Historic District has architectural significance because its buildings include many well-preserved examples of particular architectural styles and periods, from the vernacular architecture of rural colonial New England, simple in form and plainly detailed, to the highly embellished Colonial Revival style of the early 20th-century.

The Woodstock Hill Historic District's Colonial style dwellings exhibit the typical features of 18th-century New England domestic architecture: clapboarded exteriors, symmetrical five-bay facades with center entries, and small-pane divided sash. A greater number of buildings display the defining characteristics of the Federal style, such as slender corner pilasters, fanlights, and denticulated cornices. Among these, the First Congregational Church is an outstanding example; its Palladian window, narrow cornices embellished with dentils, and semi-circular fanlights above the entranceways and on the front gable epitomize the delicately scaled interpretation of Classical and Renaissance motifs that was at the heart of the style. The meetinghouse was the work of John Truesdell, one of a family of architect-builders responsible for numerous elegant houses and public buildings in Woodstock, Killingly, and Rockville, Connecticut. The Federal style is also embodied in the narrow lines of dentils on the cornice and pedimented front entry of the John Napping House, 512 Route 169 (built in 1806 and enlarged c.1820). These buildings illustrate the use of Classical details that was the core of the style. The greater formality of architecture in this period is reflected in the turn towards center-hall, hipped-roof house forms, abundantly evident in the dwellings of Woodstock Hill.

The heavier proportions that characterized the classical elements of the Greek Revival style are clearly evident in the district in the John Bartholomew House at 540 Route 169 and the Caleb Fenner House, 519 Route 169, which exhibit deep cornices, pilaster-and-lintel entries, and wide corner pilasters.

The Woodstock Hill Historic District includes several notable examples from the Victorian period. Henry C. Bowen's Roseland Cottage is a nationally known example of the Gothic Revival style. Designed by the English-born architect Joseph Collins Wells, it features Gothic Revival details such as steeply pitched gables with elaborate vergeboards, pinnacles, stained glass, pointed-arch windows with diagonal sash, and intricate porch trim. The Italianate style is illustrated by the 1873 Woodstock Academy building's hipped roof, bell tower, and wide overhanging eaves supported by large brackets.

The Woodstock Hill Historic District also has some notable examples of early 20th-century revival styles. The elaborate Georgian precedents favored by the Colonial Revival movement are evident in the Arthur Sherburne Hardy House's Palladian window, small oval lights, colonnaded porch and entry, and balustrades along its hipped roof. Medievalisms such as a stone and stucco exterior and buttresses revive Tudor architecture in the Bracken Library, while the Palmer Memorial Hall at 523 Route 169 embodies the Neoclassical style in its blocky dentils and large arched windows.

Landscape Architecture Significance

New England town commons in the 18th century were not particularly well-defined as separate landscape entities: they received little attention and many times were not articulated from highway right-of-ways, school yards, church grounds, and other public space. It was generally not until the middle of the 19th century that the village green emerged as a park-like focal point of the town center, often as a result of a village-improvement society or other philanthropic effort.

Woodstock's small common is an example of this development. Henry C. Bowen provided funds for its improvement in 1853, at which time oak, maple, and beech trees were planted around the periphery. Bowen also contributed to its ongoing maintenance as a park, and helped establish it as a ceremonial center by financing elaborate Fourth of July events there. The ceremonial and memorial aspects of the Common were furthered by the siting of two boulders as war monuments at the Common's southern end. Today, the Common continues to function as a visual focal point for the village and as an enhancement to the setting of important buildings such as the Academy, Bracken Library, and the two churches.


Bayles, Richard M. History of Windham County, Connecticut. New York: W.W. Preston and Company, 1889.

Bowen, Clarence W. The History of Woodstock, Connecticut. Norwood, Massachusetts: Plimpton Press, 1976.

Kelly, J. Frederick. Early Connecticut Meetinghouses, Vol. II. New York: Columbia University Press, 1948.

Larned, Ellen. History of Windham County, Connecticut. 2 vols. Worcester: priv. pr., 1874, 1880.

Lincoln, Allen B. A Modern History of Windham County, Connecticut. 2 vols. Chicago: S.J. Clarke, 1920.

Slater, James A. The Colonial Burying Grounds of Eastern Connecticut and the Men Who Made Them. Hamden, CT: Archon Books, 1987.

Woodstock Hill Historic District Report. Woodstock: Woodstock Historic District Commission.

Woodstock Tercentenary Committee. Heritage and Horizons — Woodstock Remembers 300 Years. Woodstock, 1896.

Maps and Views:

Barber, John W. Connecticut Historical Collections. New Haven: Durrie & Peck, 1838.

Gray, O.W. Atlas of Windham and Tolland Counties. Hartford: C.G. Keeney, 1869.

‡ Bruce Clouette and Hoang Tinh, Historic Resource Consultants, and John Herzan, Connecticut Historical Commission, Woodstock Hill Historic District, Woodstock, Windham County, CT, nomination document, 1997, National Park Service, National Register of Historic Places, Washington, D.C.

Street Names
Academy Road • Cemetery Road • Child Hill Road • Old Hall Road • Plaine Hill Road • Route 169 • Roxbury Road

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