7 Towns in Vermont With Rich History
What says New England like Vermont? The state conjures picture-perfect scenes of the celebrated American northeast, from the Green Mountains and fire-colored fall leaves to stone-built houses and idyllic small-town life. Earning statehood in 1791, Vermont has evolved from industries like textiles and stone quarrying to its current status as a major tourism destination. The state's motto for travelers — "Vermont, Naturally" — fits well, given its rivers, mountain views, and even a section of the Appalachian Trail. For history and beauty in one place, head to Vermont's small towns like these.
Dorset
Tucked into Vermont's southwest corner, not far from the New York state line, Dorset, with 2,200 citizens, could stand in for postcard New England. Its natural sites run long, including Dorset Peak, Emerald Lake State Park, Bromley Mountain, and the Dorset Hollow hiking zone. History, Dorset hosted a number of meetings that accelerated Vermont's path to statehood. The town, a former quarry site, supplied marble for the New York Public Library and other noted buildings. The town also claims fame for something very different: it is the birthplace of William Griffith Wilson, also known as Bill W., founder of Alcoholics Anonymous, the worldwide support network.
Winooski
Winooski, population 8,300, sits north of the Winooski River in northwest Vermont. The town hosts the Mill Museum as well as the Winooski Historical Society, which remembers the town's past as a wool-processing center and textile manufacturer. These days, Winooski offers performing arts and other cultures in abundance. Saint Michael's Playhouse puts on dramatic performances of all kinds. Architectural gems include St. Francis Xavier Church, with its trademark double spires made of copper, as well as the locally famous stained-glass windows at the Methodist Episcopal Church of Winooski. For fresh air, head to Memorial Park for riverside paths. Skaters of all ages may prefer the Landry Park Skateboard Park.
Essex Junction
Essex Junction, slightly larger at 10,900 residents, sits to the south of the Winooski River, just east of Winooski. The town separated from the town of Essex in 2021 for tax reasons, making Essex Junction a newly formed place to explore. The town is a well-known hub of state industry, with IBM and other high-tech manufacturing long a part of local economic life. Travelers should visit Essex Junction in September during the Champlain Valley Fair. Running for more than a century, the ten-day series of 4H-style events honors Vermont's diverse agriculture. Past iterations have drawn up to 300,000 attendees, partly to see major music stars perform. Past acts have included pop giant Justin Bieber and pop-country hero Darius Rucker, sometimes referred to as "Hootie" from nineties rock band Hootie and the Blowfish.
Woodstock
Woodstock, which is distinct from the town and 1969 cultural moment in upstate New York, is home to 3,000 souls. This southeastern town attracts plenty of history and architecture buffs. The Woodstock Village Historic District offers standouts like the Lincoln Covered Bridge, built in 1877, and the First Congregational Church, from 1890. Other noted buildings include the Norman Williams Public Library, which was finished in 1884. The town made history more recently through its "Wireless Woodstock" plan, which blankets the district with free internet. For greenery, head to Woodstock Town Forest, which is south of town. The Marsh Billings Rockefeller National Historical Park gives spectacular views of the area — and it is the only part of the US National Park system in Vermont aside from the Appalachian Trail.
Manchester
Manchester, population 4,500, sits in southwest Vermont and takes its eastern limit from the Batten Kill River. The town is known best for Hildene, the estate of Abraham Lincoln's son Robert, which boasts a very large Georgian Revival mansion completed in 1905. Though very small, the town boasts three separate historic districts: Bonnet Street, Main Street, and a neighborhood known as The Depot. In a reflection of Vermont's vacationland traditions, the American Museum of Fly Fishing opened in 1968, shows old rods, tackle, and gear of all sorts. Manchester also is the headquarters of the fishing and clothing brand Orvis, much-loved among older Americans. Other outdoorsy types will want to hike Mount Equinox or in the nearby Green Mountain National Forest.
Grafton
In the midst of the Green Mountains, Grafton, with a mere 600 residents, lies in Vermont's southeast. The former wool-raising and textile mill town, sited here for its position by the Connecticut River, now focuses on vacationers and other tourists. Grafton also runs a world-famous cross-country skiing center, ideal for champions-in-training and amateurs alike, which in warm weather turns its trails into a mountain-biking zone. The center's kid-centered summer bike camp brings in youngsters from New England and beyond. For foodies and fans of high-end cheeses, Grafton offers some of the best artisanal cheese in the country, as the Grafton Village Cheese Company will attest. For a town so small, Grafton keeps very busy.
Chester
Chester, population 3,000, sits to Grafton's north on the picturesque Williams River. A tributary of the Connecticut, the Williams provides beautiful scenes for fishing, swimming, and relaxing in warm seasons. Chester Town Forest, with two separate zones north and south of town, offers even more fresh air. Chester has not one but two historic districts, both listed on the National Register of Historic Places. The Stone Village preserves granite houses from past centuries, while Chester Village shows beautiful buildings from antiquated building styles, including Victorian, Federal, and Colonial Revival. The town puts on its Fall Festival every September, as well as a Winter Carnival each February.
Vermont's Finest Scenes Hide In Its History-rich Towns
Vermont's smaller, historic towns attract tourists of every taste and type. The state balances the always-new with the ever-older — like in Essex Junction, which offers free internet and tech innovation as well as the enduring traditions of its agricultural fair. Winooski, Woodstock, and Manchester all boast stately architecture and historic homes. Mountain towns like Grafton only confirm the best stereotypes of Vermont as a picture-perfect New England state. For a small state with even smaller towns, Vermont's natural and cultural gems make for a big, beautiful visit.
