Nestled in the hills of Vermont lie some hidden gems: centuries-old towns with quaint Main Streets and rolling green hills. From Stowe to Burlington, towns within the Green Mountain State are doing their part to keep their historical charm alive by offering unique artisan shops and historic sites for visitors to explore.
Each of these small towns provide an abundance of culture and adventure at every turn! Explore nine of the cutest small towns in Vermont worthy of any traveler's itinerary so that you can plan your perfect trip through The Green Mountain State.
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Stowe

The historic village center is one of the most photographed spots in Vermont; it features classic architecture with brick storefronts housing local shops and restaurants alongside century-old churches and homes. You'll also find some great art galleries around town, like the Helen Day Art Center and Northwood Gallery where they showcase local artists. When it comes to dining, Stowe has something for everyone. From cozy diners offering home-cooked comfort food to fine restaurants serving up delicious dinners, there's a place here to please every palate.
Woodstock

The downtown area features many quaint stores, restaurants, and galleries. If you're interested in shopping local goods, try checking out the Woodstock Farmers Market or one of the many antique shops located around town. The main street alone has a variety of cafés and bistros with delicious food options that are sure to please all taste buds. Other popular attractions include the Quechee Gorge and Billings Farm & Museum. Woodstock is truly an idyllic destination for those looking to get away from it all and explore the great outdoors in beautiful Vermont.
Village of Manchester

Start your visit with a stroll down the quaint streets of downtown Manchester, lined with an array of independent shops, cafes, and art galleries. Explore the many specialty stores offering local artisan products perfect for souvenirs or gifts. For foodies, there are plenty of restaurants ranging from cozy pubs to high-end eateries serving up delicious regional dishes. For outdoor activities, Manchester has something for everyone! Pack a picnic and head out to one of the nearby lakeside beaches or hiking trails. A popular spot is Hildene Historic House, a beautiful estate offering trails through the grounds and gardens.
Quechee

For those looking to get outdoors, Quechee is a great place to explore. Take a hike through Quechee State Park or visit nearby Ascutney Mountain for incredible views of the surrounding valley. If you're feeling adventurous, there are plenty of activities such as mountain biking, horseback riding, skiing, and snowshoeing available in the area.
Grafton

The town is home to dozens of historic buildings. These gorgeous structures are filled with stories about Vermont's past and can be explored at leisure by anyone visiting Grafton. For those looking for an educational experience, the Grafton Historical Society operates a museum where you can learn all about the town's past. The community of Grafton is also renowned for its festivals and throughout the year, visitors can enjoy live music craft shows, parades, and much more. In addition to these festivals, there are also numerous farmers' markets that bring locally produced goods to Grafton from surrounding areas.
Brattleboro

Commercial stores and restaurants in the New England town of Brattleboro, Vermont, via jenlo8 / Shutterstock.com For outdoor enthusiasts, there are plenty of activities to choose from, such as skiing on nearby Mount Snow or going kayaking on the Connecticut River, which runs through town. Local parks like Living Memorial Park are great places to take a walk or go for a bike ride and there are numerous hiking trails nearby too! Don't forget to check out the First Congregational Church, a National Historic Landmark built in the 1800s. Despite being one of Vermont's larger small towns, Brattleboro still has that cozy feel and appeal that makes it stand out from the rest. With its charming atmosphere and great variety of attractions, it's no wonder why Brattleboro is one of the cutest small towns in Vermont.
Shelburne

The downtown area is home to quaint cafes and restaurants as well as unique boutiques and specialty shops selling local produce and handmade crafts. If you're feeling daring, try renting a bike to explore the nearby countryside or take part in some fun events like a wine tastings or art gallery openings. The Shelburne Museum is a must-see with its eclectic mix of art, history, and architecture.
Killington

Take a stroll through downtown Killington for all your shopping needs or visit one of the many local art galleries to explore pieces from local artists. Enjoy a bite to eat at any number of restaurants serving up delicious food for breakfast, lunch, and dinner; some with stunning views of the mountains. For those who want to explore more, visit Pico Mountain. It offers some of the most spectacular views in all of New England. Kayaking and fishing on nearby rivers is also popular during spring and summer months. Horseback riding is another great way to experience Killington's natural beauty.
Burlington

Visit Church Street Marketplace for boutique shops and art galleries. A summer concert series is offered in Battery Park at Waterfront Park during the warmer months. There are also plenty of opportunities to enjoy nature. The University of Vermont is located in Burlington, so there are lots of student-friendly bars and restaurants as well as cultural activities such as art exhibits, concerts, and theater productions all year round. Make sure to explore nearby artsy neighborhoods like Hill Section for charming views, historic architecture, and unique shops.
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