Windsor County Vermont

Fullerton Inn // 1921

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The Fullerton Inn, overlooking the Town Common in Chester, Vermont, is an imposing Colonial Revival style hotel that has been in operation through many iterations, and contributes to the strong commercial character of the Chester Village streetscape. The inn was first developed here following the arrival of the railroad to Chester, which brought new business and travellers to the formerly agrarian and light industrial community. The original 1862 inn building, known as the Ingraham House, was destroyed following a large fire in the village, and its replacement burned as well in January 1920. Within a year, the present building was built from the ashes in a style typical of the early 20th century, Colonial Revival. Dominated by the large slate-shingled gambrel roof and projecting front veranda, the building’s most iconic feature is said to be inside, a fireplace inside the lobby which contains 27 stone varieties from the area.

Frederick Fullerton House // 1861

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This distinctive Italianate Villa style house in the charming village of Chester, Vermont, was built in 1861 for wealthy merchant, Frederick Fullerton (1817-1869). Mr. Fullerton worked in his family’s mercantile business in Chester, and was involved with cotton manufacture in Springfield and with the Cavendish woolen mill managed by his older brother, Henry, who built an equally distinctive residence in Cavendish called “Glimmerstone“. Basically cubic with asymmetrical gabled corner pavilions, the Fullerton House is an excellent example of an Italianate Villa with bracketed cornice, two-over-two sash windows, a wrap-around porch, and second floor balcony with a bracket-supported hood with decorative valance and an oculus window above. The residence is said to have been designed by architect, William P. Wentworth, who designed the St. Luke’s Episcopal Church across Main Street a decade later.

Yosemite Engine House // 1879

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The Yosemite Engine House on Route 103 in Chester, Vermont, is a unique and iconic architectural landmark that has stood for almost 150 years. Chester’s second fire district was established in 1871, following a number of large fires in the village, prompting funding from businessmen and the town for a new engine house. Built in 1879, the Yosemite Engine house was built as a fire station for the village defined by its rectangular massing, first-floor engine hall, second-floor meeting hall, and twin bell and hose-drying towers that are capped by mansard roofs. The station originally housed horse-drawn and human-operated fire engines until the 1920s, when the doors were enlarged for the first engine-powered fire truck. The fire district, a separate taxing entity from the town since its creation, was dissolved in 1967, and its properties, including this iconic fire station, reverted to the town. It was eventually sold into private hands, and was operated for a short time as a museum by the local historical society before being reacquired by the town in 2018. The building is awaiting a full restoration.



Amos Heald House // 1803

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This large brick Federal period house in Chester, Vermont, was built in 1803 and is said to have been a stop on the Underground Railroad. The large residence was built for Amos Heald (1767-1849), who was born in Concord, Massachusetts, and when just a boy of nine years, Amos witnessed the Battle of Concord kicking off the American Revolution. In about 1777, his father, Daniel Heald, moved the family to Chester, Vermont, which was then named New Flemstead, to escape the conflict. Daniel Heald acquired land near the Williams River and built a large Federal style home. He later deeded his son, Amos, land on which he too would build a residence. Amos Heald lived in this brick home and served in many positions in town until his death. The estate was bequeathed to his son, Amos Heald Jr. (1804-1873), who also served in the town offices. Locals state that Amos would shelter escaped enslaved people from the south on their way north to Canada. After his death, his son Prescott took over the property and built a wood-frame addition off the rear stables and barns, which became the town clerk’s office during his tenure, as well as the office for his insurance business. Sometime in the 19th century, the house was renovated with the addition of porches, and later, the building became the Weathervane Inn.

Daniel Heald House // c.1785

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Daniel Heald (1739-1833), one of the earliest settlers in the town of New Flamstead (later renamed Chester) Vermont, established his farm on the west side of the upper Williams River. He moved to rural Vermont from Concord, Massachusetts, where he was one of the Patriot soldiers who at the Concord bridge, fought against the British troops while his wife and children who had fled from their home viewed the battle from a neighboring hill. He, with his family, emigrated to Vermont in about 1776 and eventually would serve as town clerk from 1779 to 1799 and as town representative from 1783 to 1797. Around 1785, he built this residence, oldest wood-frame house in North Chester, a two-story, central-chimney house with saltbox roof sloping to the rear. When his son, Amos Heald, was of age, some of the property was deeded to him, where he built a stately Federal style residence that stands across the street to this day. Both of the Heald houses tell the early history of Chester through well-preserved houses.

Chester Public Tomb and Hearse House // 1850

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Near the entrance to the Brookside Cemetery in the charming village of Chester, Vermont, these two very different looking buildings were constructed for one purpose, death. Before the proliferation of funeral homes and cremation, infrastructure for the dead was a necessary piece of the built environment for towns and cities all over the region. The wood-frame building seen here was built as a hearse house, which would shelter the horse-drawn hearse for the town. Prior to the advent to funeral homes, most wakes were held at the home of the deceased, after-which, the body would be transported by the horse-drawn hearse to the cemetery for burial. This was followed by a memorial service at the nearby church. If the ground was frozen or if the family did not yet have the funds to bury their family member, the body would be held in the public tomb until the burial. The Chester Public Tomb dates to 1850 and was built by local mason, Arvin Earle from stone  quarried near Gassetts, a hamlet in the north part of Chester that was shipped to Chester Depot by the newly completed railroad. While no longer in use, these two vernacular buildings hold a very important history of the town and have been lovingly preserved by local residents. 

Chester Congregational Church // 1828

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A significant landmark in Chester, Vermont, the Congregational Church of Chester is a sophisticated interpretation of ecclesiastical Federal architecture. Built in 1828, the soaring, five-stage clock-and-bell tower with bellcast cap and weathervane rises above a pedimented three-bay entrance pavilion with semi-elliptical fanlight, a common motif in the style. It is believed that local carpenters, Comfort Carpenter Dresser and his son, Charles Dresser, built the church, likely from planbooks for specific details. The church originally served as the Union Meeting House for Congregational, Methodist, and Universalist parishioners until around 1848, when other churches set off to build their own structures, after this, the Congregationalists remained here. Today, due to years of dwindling membership and a small population in the surrounding area, the church is “replanting” to reactivate membership and realign with community needs. Hopefully this significant church will be preserved in the future, possibly through preservation grants!

William Pollard House // 1899

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This high-style and ornamental house in Chester, Vermont, ranks among the state’s best examples of the Queen Anne style. The residence was constructed in 1899 for William Pollard (1854-1941), a local businessman who owned a shirtwaist manufactory in town with his brother, who lived next door. The painted-lady Victorian house features an asymmetrical plan highlighted by a three-story octagonal corner tower that is surrounded by a wrap-around porch with a delicate spindled frieze. The use of accent colors in the paint scheme further highlight the millwork details on the residence, which have all been preserved for well over a century. 

Chester Masonic Temple // 1907

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Built in 1907, this handsome building on Main Street in Chester, Vermont, has long been the home to the Olive Branch Lodge 64 of the Freemasons, an international fraternal organization. Colonial Revival in style, the building features corner pilasters that support a denticulated entablature along the eaves of the slate hip roof. A projecting portico over the front entrance is supported by classical Ionic columns. The 1920s marked a heyday for Freemasonry, especially in the United States. By 1930, over 12% of the adult male population of the United States were members of the fraternity. Following the Great Depression and WWII, membership sharply declined in fraternal organizations, like the Masonic Temple. A number of years ago, the Lodge here moved to a new building in a nearby town, and a local law firm purchased the building and spent 18 months renovating the building for use. Today, the historic character and even symbology remain on the building, while it houses a local business. 

Comfort C. Dresser House // 1799

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Built just before the turn of the 19th century, this handsome five-bay vernacular Federal period house is located on the charming Main Street of Chester, Vermont, and is one of the oldest extant houses in the village. The residence was built in 1799 by Comfort Carpenter Dresser (1777-1856), who with his family, moved from Bridgewater, Massachusetts, to the town of Chester, where he found work as a carpenter and housewright, a fitting profession due to his middle name. The family resided here for nearly 30 years until they moved to New Hampshire. The beautiful home, painted a bright white sometime in the 20th century, features a front door with sidelights, 12-over-12 sash windows, and a symmetrical facade, common for the style.