8 Unforgettable Small Towns to Visit in Vermont

Vermont is Green Mountain country and aptly dubbed the Green Mountain State. It is the second least populated state in the US, so residents and visitors can truly immerse themselves in the stunning natural beauty of the surrounding landscape. Vermont is also famous for Ben & Jerry’s, and it’s common to see families strolling through the quaint city streets, enjoying a cone, and gaping at the impressive greenery (or fall foliage), depending on the season. For an unforgettable Vermont trip, there is no better place to start exploring than the gorgeous small towns that make up the state.

Manchester 

Manchester is one of the trendiest places in this spectacular state. The white church steeples tower above the small-town streets that turn into a snowy wonderland in winter. Manchester is also one of the only places in the US where visitors will find an agricultural center with an on-site Nubian goat herd and 24 designer outlets, including Giorgio Armani, Ann Taylor, J. Crew, Ralph Lauren, and more. Besides this, Manchester is home to the magnificent Lye Brook Falls and The Equinox Preservation Trust with its serene pond. The Hildene Estate, once home to the Lincoln family, is worth a day trip, while the Benson Hole is the perfect place to cool off on a hot day. For those who want to get their biking on, the Marble Rail Trail tracks through the forest, past fields where horses roam, and clear water streams.  

Stowe 

Stowe is the place to go for a musical adventure or, at least, a historical adventure. It is where visitors flock to see the Trapp Family Lodge, the former home of the famous van Trapp family. The lodge looks like it was plucked from Austria and plonked onto the Vermont landscape. Here, visitors can ski, dine, and stay over for a night or two to really take in the atmosphere.  

This unforgettable small town is famous for the Stowe Mountain Resort, where people can enjoy an alpine village setup with hiking, mountain biking, snowboarding, skiing, and zip-lining. Moreover, Stowe offers the splendor of nature with the Stowe Recreation Path, Moss Glen Falls, and Smugglers Notch State Park. There is also the Sterling Gorge Falls in the Green Mountains, which are a must-visit, and several historic bridges perfect for those must-have selfies.  

Woodstock 

Woodstock may sound like a place for non-stop music festivals, but this small town is actually famed for offering visitors the chance to experience a working dairy farm. Billings Farm & Museum gets people up close with farm animals and shows them the best of farm life. The on-site museum is a fantastic way to spend an hour or two learning about Vermont’s rural heritage. Further afield, the Marsh-Billings-Rockefeller National Park provides a fascinating insight into American history, while the Ottauquechee River beckons those with picnic baskets and cameras in hand. Often referred to as the prettiest small town in America because of its backdrop of hills, forests, and scenic landscapes, Woodstock is also home to heritage farms that highlight agricultural traditions and promote local products.  

Waitsfield 

Waitsfield is an unforgettable small town with a big skiing community. Here, the Mad River Valley offers skiing and snowboarding in winter, as well as hiking and biking when the weather turns warm. And not too far away, the Mad River Glen in Fayston is one of the best skiing resorts in Vermont, if not the US. The roads around Waitsfield are as gorgeous as the town itself, with Vermont Route 100 being one of the most popular road trip routes. Moreover, the town has a booming arts and culture scene with the Mad River Glass Gallery and the Big Picture Theater & Café. Waitsfield is known for its unique combination of scenic splendor and welcoming locals. Those who visit can’t help but vow to return.  

Bennington 

Bennington is one of the most historically important small towns in Vermont. It houses the imposing Bennington Battle Monument. The monument commemorates the Battle of Bennington during the American Revolutionary War. Downtown Bennington also highlights the history of the town and sports well-preserved architecture. Furthermore, the Bennington Museum houses incredible historical artifacts from the days of Vermont past. Bennington is also where the home of famous poet Robert Frost still stands. He wrote many of his poems within the walls of the Shaftsbury house.   For those who love walking, Lake Shaftsbury State Park offers stunning views of its lake from the walking path. It is also a magnificent setting for a picnic or late afternoon swim. The White Rocks/Bald Mountain trail is a great hike, while Lake Paran is great for kayaking.  

Brattleboro 

Brattleboro, another unforgettable town in the great state of Vermont, is known as the home of Tasha Tudor. Fans can visit the Tasha Tudor Museum to learn about the life and times (and works) of this beloved American author and illustrator. The town loves expressing itself in the form of art and culture and has started a monthly Gallery Walk for locals and visitors to explore different art venues. There is also the Vermont Maple Museum, where visitors can experience the production of Vermont’s delicious maple syrup first-hand. Outside of the town limits lies Retreat Trails. which offers hiking and ample opportunities to take photos of the tranquil nature setting.  

Grafton 

Picturesque Vermont extends to the lovely village of Grafton, a charming place that holds the popular Grafton Trails and Outdoor Center. Stretching over 2,000 acres of land, the center is one of the best places in Vermont to explore nature trails and go cross-country skiing. Likewise, Grafton Ponds Outdoor Center is heaven for outdoor enthusiasts. It offers breathtaking mountain views and is a great area for skiing. 

Grafton also indulges in Vermont’s maple syrup history, and Plummer’s Sugar House allows visitors to sample maple products and see the sugaring process in action. For those who want to know more about this unforgettable little town, there is the Grafton Historical Society, which displays several exhibits and collections highlighting what life was like in Grafton many years ago. 

Rutland

When someone mentions Rutland, most people immediately picture the Paramount Theatre. The theatre is famous for live shows and concerts and is an unforgettable stop in this pretty town. Rutland is also chockful of historic sites and has nearly 75 national registry landmarks and museums. This makes it a dream destination for those who love delving into the history of small towns. Rutland caters to nature lovers, too, with Deer Leap Trail not too far away near Killington, a marvelous hiking trail, and Green Mountain National Forest, where people can hike, camp, and watch wildlife pass by. For the skiers, Pico Mountain offers days of skiing and snowboarding fun.  

Vermont is the ideal destination for those who love mountainous landscapes and skiing. The small towns here offer an unmissable chance to escape the doldrums of ordinary life and enjoy the finer but also simpler things, even if it’s just for a short time.