Comfort C. Dresser House // 1799

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. 

Simonsville Schoolhouse // 1856

One-room schoolhouses like this example in the Simonsville area of Andover, Vermont, have been commonplace throughout rural portions of New England where children of most ages would share the classroom and be taught everything from basic spelling to math. The Simonsville schoolhouse was built in 1856 and is a typical example of a vernacular one-room schoolhouse in rural New England, with no frills or ornament, just a house of learning. The Simonsville Schoolhouse was converted to a residence sometime in the latter half of the 20th century and has been renovated, keeping the basic form and interior floorboards from the 1850s. The school-turned-home is currently (2025) listed for sale.

Green Mountain Hall // c.1860

This simple Greek Revival style country church in Whitingham, Vermont is similar in form to the Methodist Church (last post) with a gable front double entry, large full pediment, corner pilasters, and centered two-tiered steeple. Also like the Community Church nextdoor, this was built circa 1860 as a church, but for the Universalist Unitarians in town. In 1892, the church was transferred to the Green Mountain Club, giving it the informal name “Green Mountain Hall,” and in 1905 the Town of Whitingham took it over. The building was used for dances, meetings, social gatherings, and other events until the Whitingham Historical Society took it over in a lease in 1971 to develop into a museum. The well-preserved vernacular building with its c.1920 front porch is a great representation of Vermont architecture, reuse for new uses and update. No waste, and a whole lot of charm!

Abraham Chase House // c.1860

One of the cutest old houses in Whitingham Village in Vermont is the Abraham F. Chase House, just a stone’s throw from the country store and post office. Abraham Chase was a dealer in dry goods, groceries, boots, shoes, and hardware in this village, possibly from half of this building. The vernacular one-story clapboarded frame house has some Gothic details like the rear steep double gable wall dormer. I am actually a huge fan of the green doors and newer stone porch wall, they really make this cottage pop!

Belding Homestead // c.1820

David Belding (1785-1860) was born in Swanzey, NH and at 25 years old, moved to Moretown, Vermont in 1810, marrying an eighteen-year-old Florinda Freeman a year later. The couple built a farmhouse on the outskirts of town near a brook. David worked as a farmer and would later officiate as a justice of the peace, the town lister, selectman, and represented the town in the State Legislature for two terms. From his enhanced wealth, David appears to have expanded his farmhouse in the 1820s or 30s with this vernacular Federal and Greek Revival style residence. The Belding Homestead would remain in the family for decades and eventually became the Belding House Bed & Breakfast.

Moretown Town Hall // 1835

The township of Moretown, Vermont was chartered on June 7, 1763 by Governor Benning Wentworth of New Hampshire. The original charter contained approximately 23,040 acres of land to be divided into about 65 shares of proprietors. Active settlement did not occur until after the Revolutionary War with early buildings constructed on the Winooski River (the northern boundary of the town) and subsequent development along the Mad River (which cuts through the middle of town). Saw and grist mills were built and the town developed as a rural farming and industrial community on the rivers. The Moretown Town Hall was erected in 1835 in the Greek Revival style. It has a pedimented portico with Doric columns that support a large pedimented gable peak in imitation of a Greek temple. Like most buildings in the Mad River Valley, the building is unapologetically Vernacular which means it relies on local materials, local builders, and not on architect-designed finishes. This is an aspect of Vermont architecture that makes the state so charming.

Coolidge Cheese Factory // 1890

Does it get more Vermont than a cheese factory?! The Coolidge Cheese Factory in Plymouth Notch, Vermont was built in 1890 by Col. John Coolidge (President Calvin Coolidge‘s father), James S. Brown, and two other local farmers so that they would have a convenient market processing milk produced by their farms into cheese. The vernacular building was a short walk from the original Coolidge home and is evocative of many such buildings in rural Vermont. The cheese factory continued to operate until the 1930’s. The factory was renovated in the early 1970s in honor of President Coolidge’s 100th birthday and now produces cheese according to the original formula. The cheese would make a great Christmas gift!

Laura Wade House // 1935

This charming cottage in Dorset is one of four houses in the village which were moved here by Charles Wade in the 1920s and ‘30s. Wade was born in Dorset and saw declining population with the marble industry failing. He sought to re-invigorate the town by advertising its natural beauty and brought in homes and buildings from nearby to fill the “missing teeth” (including the building that presently houses the Dorset Historical Society). Assembled from parts of various Enfield, Massachusetts buildings moved to Dorset this 1½-story, wood-framed, clapboard house stands on a marble ashlar foundation and is said to have been built by Wade for his daughter, Laura Wade.