Brick buildings housing shops lining a bustling street at sunset in Woodstock, Vermont, USA.

These Historic Towns in Vermont Are Worth Exploring

Also known as the “Green Mountain state” for its unique topography and vast expanses of forests. Vermont was founded on March 4th, 1791, with 233 years of history and counting. It is no wonder that each of these small towns possesses such an extensive history. Explore the unique charm and rich histories of Vermont's captivating towns. From the quaint capital of Montpelier, where the Vermont State House narrates the state's story, to the historical treasures of Bennington, like the Bennington Battle Monument, each town offers a fascinating journey into the past through a variety of historical, natural, and scenic landmarks.

Montpelier

Montpelier, Vermont, USA town skyline during autumn.

Montpelier, Vermont, USA town skyline during autumn.

Begin your day in Montpelier by strolling through the historic downtown whilst exploring local shops and having breakfast at a cozy café like La Brioche. After, take a guided tour of the Vermont State House, which invites you to explore the history of the state and local area. Next, venture to the Vermont History Center Museum to continue your journey into Vermont's past. For lunch, savor farm-to-table cuisine at the Three Penny Taproom, which serves up some of the finest meals made from local produce. Dedicate your afternoon to exploring the Rock of Ages Granite Quarry, where a guided tour takes you to an overlook of the largest operating granite quarry in the world. Before retiring for the night, attend a performance or event at the Lost Nation Theater for a cultural touch in this vibrant Vermont capital.

Bennington

Horizontal view of Vermont's first Protestant church, the "Old First" Congregational Church, located in Old Bennington, VT, USA. Built in 1805 by Lavius Fillmore, it stands as a historic landmark.

The "Old First" Congregational Church, Bennington, VT, USA. Editorial credit: Brian Logan Photography / Shutterstock.com

This historic town in the southern portion of Vermont is an excellent place to visit if you’re looking for a rich history. Start your day in Bennington with a visit to the Bennington Museum, which houses a variety of artifacts and art that represent the town's heritage. Next, Explore the iconic Old First Church that was founded in 1805, and for an eerie experience, explore its historic cemetery. Don't miss the Bennington Battle Monument commemorating the pivotal Battle of Bennington during the American Revolution; this historic site was once a battlefield that played a significant part in shaping the country’s future.

In the afternoon, venture to the Robert Frost Stone House Museum and learn about the renowned poet's connection to the region, drawing inspiration from the scenic beauty that immerses the town and inspired the poet’s literary works. Conclude your historical journey with a scenic drive to the Bennington Center for the Arts, which is known for showcasing diverse exhibitions that provide valuable insights into this historic town's culture.

St. Johnsbury

 Historic buildings on Railroad Street in downtown St. Johnsbury, VT, USA.
Historic buildings on Railroad Street in downtown St. Johnsbury, VT, USA. Editorial credit: Wangkun Jia / Shutterstock.com

Surrounded by the scenic beauty of Vermont, St. Johnsbury has long been a place that is home to a unique past that can’t be replicated anywhere else. When visiting “St. Jay,” as locals refer to it, a stop at the Fairbanks Museum and Planetarium is essential. Established in 1889, the museum houses an extensive collection of natural history specimens, artifacts, and a vintage planetarium. For an outdoor historical experience, march to the St. Johnsbury History and Heritage Center, where exhibits and walking tours showcase the town's industrial and cultural history. Take a journey out to one of the best hiking trails in the state; Lamoille Valley Rail Trail is a 4-season trail that runs near the town, so be sure to get out and enjoy the great outdoors that Vermont is known for. After a busy day of exploring this town’s historic landmarks, refuel for the next by enjoying a nice meal at the Kingdom Taproom or Salt Bistro, which offers some of Vermont’s finest cuisine.

Burke

Aerial view of East Burke, Vermont, showcasing the town and surrounding mountains in vibrant fall colors on a sunny day.

Aerial view of East Burke, Vermont.

This town is a perfect destination to escape the hectic routines of everyday life, whether it’s skiing in the winter or hiking in the summer. Burke is an ideal spot, regardless of the season. The town is prominently known for hosting one of the best ski kills in all of Vermont; Burke Mountain has some of the freshest powder on the East Coast and has long been attracting skiers and snowboarders. During the summer months, explore the scenic Kingdom trails that intertwine through the heart of the local forests and offer some beautiful views of Vermont; visit during fall to see the jaw-dropping blend of natural beauty as the leaves change color. A prominent historic landmark within the town is the Darling State Historic District, which covers 2’000 acres on the outskirts of the town. For a whole new experience, book a visit to D-N-D Stables Guided Trail Rides, which allow you to enjoy the beauty Vermont has to offer from horseback.

Middlebury

Middlebury Falls, a scenic waterfall located in Middlebury, Vermont.

Middlebury Falls is a scenic waterfall located in Middlebury, Vermont.

Settled at the base of the towering Green Mountain, Middlebury offers an abundance of historical attractions that capture the essence of the town's heritage. Start your exploration at the Henry Sheldon Museum, which showcases artifacts and exhibits dating back to the town's founding in 1761. After wandering through the Middlebury Village, where well-preserved 19th-century brick has been turned into a variety of cafes, visit Costello’s market to enjoy some freshly brewed coffees. Continue your historical journey at Middlebury Falls, which is a scenic area with historic mills, bridges, and Otter Creek Falls; the area helps provide a glimpse into the town's industrial past. Get some fresh air and take a walk along the shores of Lake Dunmore; enjoy the natural scenery as this fresh body of water gives way to the looming tower of green mountains in the background. Explore the local music scene while you enjoy a fresh beverage and listen to some live music when you visit The Town Hall Theatre.

Poultney

The Original Vermont Store in Poultney, Vermont.

The Original Vermont Store in Poultney, Vermont. By Dougtone - Flickr, CC BY-SA 2.0, Wikimedia Commons

There are plenty of historical attractions that offer a captivating glimpse into Poultney's past. The exploration can begin at the Poultney Historical Society and Museum, where exhibits and artifacts chronicle the town's history, including its early settlement and development. Witness years of evolution in one afternoon by visiting the Pember Museum of Natural History, which is located a short drive away from Poultney. Also, the nearby Indian Cross Farmstead is where archaeological sites of early European and Native American settlements can be explored.

An unexpected landmark can be explored with a visit to the historic childhood home of the influential editor and presidential candidate, Horace Greeley. Also, dive into the region's mining past by exploring the Vermont Stone Trail; the trail guide features 95 sites along the trail, including the historic district of Poultney.

Plymouth Notch

Plymouth Cheese Corporation at the President Calvin Coolidge State Historic Site in Plymouth Notch, Vermont, USA.

Plymouth Cheese Corporation in Plymouth Notch, Vermont, USA. Editorial credit: Actium / Shutterstock.com

This town’s history is almost as unique as its name, and a visit to Plymouth Notch isn’t complete without a tour of the Calvin Coolidge State Historic Site. Visitors can explore the birthplace and childhood home of the 30th President of the United States, Calvin Coolidge. The site includes the family home, church, and schoolhouse, which offer a vivid portrayal of rural life in the early 20th century. It is also the place where Coolidge took the presidential oath in 1923. Also, don’t miss the Plymouth Cheese Factory, where you can witness traditional cheese-making practices and taste artisanal cheese in the heart of Vermont. To explore the town’s agricultural history, plan a visit to the Wilder Horse Barn, which is an authentic reconstruction of the original 1875 structure. This barn is now home to a vast collection of agricultural equipment from the early 20th century. When visiting this historic town, don’t forget to take a moment and breathe in the fresh air while enjoying the natural beauty of this leafy state.

Woodstock

Early autumn foliage scene featuring houses nestled among the mountains in Woodstock, Vermont.

Early autumn foliage scene featuring houses nestled among the mountains in Woodstock, Vermont.

Woodstock does not lag behind other historic towns with its unique blend of historical, cultural, and outdoor activities. Begin your exploration by visiting the Billings Farm & Museum to experience rural Vermont life and learn about the town’s agricultural history. Stroll through the Marsh-Billings-Rockefeller National Historical Park, which features a variety of nature trails and a beautifully maintained estate. To get up close and personal with nature's raw beauty, be sure to witness the Quechee Gorge, which is often referred to as the "Grand Canyon of the East" and offers some of the most breathtaking views in Vermont.

For some outdoor adventure, take a scenic hike up Mount Tom & The Pogue, which is the most popular hike in the area and leaves you looking across the vast expanse of Vermont’s forests by standing at an elevation of 650 feet. For a more leisurely trail experience, visit Mount Peg, which still provides the perfect combination of challenge and reward.

Discover Vermont's Legacy Through Its Historic Towns

Vermont's small towns offer an array of history, culture, and natural beauty. From the unique past of St. Johnsbury to the outdoor allure of Burke, each town contributes to the state's identity. Vermont's 233 years of history unfold through guided tours, museums, outdoor trails, and iconic landmarks. As you explore these towns, you'll discover a deep connection to the past, making each visit a journey through time within the "Green Mountain State."

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