ST. JOHNSBURY, VT, USA - JUL.11, 2014: Historic Buildings on Railroad Street in downtown St. Johnsbury, Vermont VT, USA.

9 Oldest Founded Towns To Visit In Vermont

Admitted to the Union in 1791, the beautiful and historic State of Vermont forms a key part of the famed New England region of America. And with stunning natural surroundings, fascinating historic intrigue, and loads of old world charm, the “Green Mountain State” is indeed a place of wondrous discovery. And as one of the nation’s oldest States, many of its towns offer an insightful glimpse into the early years of America and the growth of the region. So come explore these old and historic Vermont towns and see why the State and New England are indeed amongst the most special in the country.

Montpelier

Montpelier, Vermont, skyline view
Montpelier, Vermont, skyline view

Vermont’s capital city, Montpelier was settled in 1787 and remains one of the State’s most fascinating and attractive historic places. The smallest state capital in the nation (with only some 8,000 residents), visitors will still discover plenty of charm and intrigue in Montpelier where numerous historic landmarks can be found. These include the Vermont History Museum (dating to 1838), the Vermont State House (1833), and the stunning 194 acre Hubbard Park (1899). Here miles of hiking and skiing trails can be enjoyed, while an abundance of picnic sites and fireplace pits make the park a great place to visit in summer or winter. And with Montpelier’s vicinity to the Winooski River, calming afternoons along the waterfront are always a popular outing.

Bennington

Vermont's first Protestant church, the "Old First" Congregational Church. It was built in 1805 by Lavius Fillmore, via Brian Logan Photography / Shutterstock.com
Vermont's first Protestant church, the "Old First" Congregational Church. It was built in 1805 by Lavius Fillmore, via Brian Logan Photography / Shutterstock.com

One of two seats of the same named county, the town of Bennington traces its colonial history back to the year 1749. Today the home of just over 15,000 residents, this historic town was a key battleground during the American War of Independence (1775-1783). Commemorate the 1777 Battle of Bennington with a visit to the Bennington Battle Monument, a 306 foot tall obelisk completed in 1889 and the tallest structure in the State. In addition history lovers can also appreciate such landmarks like the Park McCullough Historic House (a Victorian style mansion built in 1864), the Old First Church (1804) and the Henry House (1769). And for a unique eating experience do not forget the charming Blue Benn Diner. Built in the 1940s it continues to serve America’s favorite and classic breakfast and hamburger favorites in a most special old school atmosphere.

St. Johnsbury

Historic Buildings on Railroad Street in downtown St. Johnsbury, Vermont VT, USA, via Wangkun Jia / Shutterstock.com
Historic Buildings on Railroad Street in downtown St. Johnsbury, Vermont VT, USA, via Wangkun Jia / Shutterstock.com

Seat of Caledonia County, St. Johnsbury can trace its history to the 1780s, and today just over 7,300 people call the town home. Located along the Passumpsic River (a tributary of the Connecticut River), St. Johnsbury is indeed a charming community where quaint natural surroundings and fascinating history come together. Visit a number of landmarks listed on the National Register of Historic Places including Railroad Street Historic District, the Franklin Fairbanks House, and the St. Johnsbury Atheneum (1871), a library and art gallery. Meanwhile an afternoon at the Fairbanks Museum and Planetarium is a great excursion for the whole family. Here in a fun and informative environment, one can learn about natural history, the wonders of space, and the historic growth of Vermont in the early United States.

Burke

Vermont Ski Area Resort in Burke VT at Sunset
Vermont Ski Area Resort in Burke VT at Sunset

Named after the 18th century English philosopher Edmund Burke, the picturesque town of Burke was founded back in 1782. Today the home to a modest population of just under 1,700 inhabitants, this charming locale lies near Burke Mountain, reaching an impressive 3,270 feet high. Popular as both a summer and winter retreat, visitors to the Mountain and town can enjoy a wonderful assortment of hiking trails and challenging skiing slopes. In the summer spend time at the nearby Lakes Crystal and Willoughby, while the stunning peaks of Mount Hor and Pisgah create a splendid framing. Meanwhile several landmarks on the National Register of Historic Places can be found in Burke including the Union Meeting House (1826), which transports visitors back to the foundational years of young America.

Woodstock

Traditional American brick buildings with shops along a busy street at sunset. Woodstock, VT, USA.
Traditional American brick buildings with shops along a busy street at sunset. Woodstock, VT, USA.

The seat of Windsor County, the historic and charming town of Woodstock was first charted back in 1761. With its strong ties to the colonial past of America, Woodstock, and its population of just over 3,000 inhabitants remains a must visit place for any lover of American history. Discover such landmarks like the Marsh Billings Mansion (1805), the Lincoln Covered Bridge (1877), and the First Congregational Church (1890) shed fascinating light on the daily life of the 18th and 19th century colonial United States. Meanwhile at the Marsh Billings Rockefeller National Historical Park, great views of dramatic rocky cliffs in addition to the historic ambience make for quite an excursion. And during the October Harvest Weekend, guests can even partake in harvesting practices popular during the 1800s.

Manchester

Morning scene of a snowy field with a silo in the distance and view of the Taconic Mountains in the background from Manchester, Vermont.
Morning scene of a snowy field with a silo in the distance and view of the Taconic Mountains in the background from Manchester, Vermont.

Manchester was first settled in the 1760s and serves as one of two seats of Bennington County (alongside the previously discussed Bennington). Home to a population of just under 4,500 residents, this scenic town is a great place to discover Vermont’s colonial past and guests can visit such landmarks like the Bennington County Courthouse (1822), the Lincoln Family Home, and the Manchester Village Historic District and its assortment of 19th century edifices. In addition at the nearby Green Mountain National Forest, wonderful opportunities for cycling, hiking, and even watching wildlife in a natural habitat make for a splendid afternoon outing for the whole family.

Warren

Crowd of skiers and lodge, Sugarbush Ski Area, via Rob Crandall / Shutterstock.com
Crowd of skiers and lodge, Sugarbush Ski Area, via Rob Crandall / Shutterstock.com

Established in the 1780s, the town of Warren is located within the Green Mountains and the Mad River Valley. A great place to enjoy the outdoors, visitors and residents alike can partake in numerous activities throughout the winter and summer seasons in a most scenic ambience. A popular ski resort destination, Warren is the home to the Sugarbush Resort, where more than 53 miles of skiing trails and some 16 ski lifts make for an adventure filled day. In the summertime, spend time at the stunning Warren Falls or trek along the famous hiking route, the Long Trail. And of course near the Mad River, calming strolls and beautiful panoramas make for a most relaxing, charming, and memorable sojourn for visitors of any age.

Stowe

Aerial view of Stowe Vermont and the Green Mountains with autumn colors.
Aerial view of Stowe Vermont and the Green Mountains with autumn colors.

The town of Stowe was established in the 1760s, some 30 years before Vermont entered the Union in 1791 and today maintains a modest population of just over 5,000 inhabitants. Nicknamed the “Ski Capital of the East”, Stowe is located within the picturesque Green Mountains and near Mount Mansfield (Vermont’s highest peak). Visitors can enjoy the slopes at the Stowe Mountain Resort (founded in the 1930s) during the height of winter, while the lush greenery of the Stowe Recreation Trail never disappoints for summer tourists. And do not forget the always fascinating Ski and Snowboard Museum, and the beloved Trapp Family Lodge that offers an assortment of athletic sport activities throughout the year.

Windsor

Aerial view of Stowe Vermont and the Green Mountains with autumn colors
Aerial view of Stowe Vermont and the Green Mountains with autumn colors

Known as the “Birthplace of Vermont”, the town of Windsor was founded in the 1760s and it was the location where the Constitution of Vermont was drafted in 1777. Today the home of nearly 3,600 residents, Windsor remains a charming and fascinating place where visitors can discover America’s past in a friendly small town atmosphere. Visit such landmarks like the Cornish-Windsor Covered Bridge (1866), the Old Constitution House (1777), and the beautiful Paradise Park. In addition the annual Autumn Street Festival is a great way to keep the whole family entertained. Here street magicians, live music, and an assortment of tasty food vendors all make this a truly fun and unforgettable day in Vermont.

Also known as the “Green Mountain State”, the historic Vermont is indeed a place of great natural beauty and fascinating American history. And with a colonial history dating to the early 18th century, visitors will never be short on old historic towns to discover, each with their own unique charm and intrigue. From the ski resort of Stowe to the town of Bennington, famed during the American Revolution, these and other historic Vermont towns are great ways to get acquainted with the burgeoning years of the United States. And with beautiful natural surroundings, even when not learning something about history, guests can always take in the sights. So wait no longer and come see why these oldest Vermont towns are truly treasures for the present.

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