11 Vermont Towns With Unforgettable Main Streets
Despite being one of the smallest states, Vermont has a big personality steeped in New England charm, agricultural heritage, and natural allure. From the shores of Lake Champlain to the foothills of the Green Mountains, the state is rich in small-town communities, each with its flavor of charm. Tourists explore their downtown hubs to get a clear picture of local character as history, culture, and commerce collide in a busy corridor.
If you are visiting Vermont for the first time, there is no better place to start discovering than the downtown cores. These promise rare historical landmarks, adorable cultural attractions, delicious farm-to-table cuisine, and inviting social gatherings, culminating in a wholesome experience. Here are Vermont towns with unforgettable Main Streets, from Burlington to Woodstock.
Woodstock
This tiny village along the Ottauquechee River is known for its rich history, covered bridges, and vintage homes. Strolling down Main Street, newcomers can explore the local art scene at Collective. This cooperative-owned gallery displays an extensive selection of handcrafts, including fabrics and jewelry. Further along the street, Red Wagon Toy Co. invites visiting families to have a fun shopping experience, from a display of clothing, toys, footwear, and more.
The Woodstock Town Hall Theatre is where the community gathers to connect with performance art. It is housed in a neoclassical concert hall and hosts a mix of film, music, and theater events throughout the year.
Bennington
Bennington is a charming New England town in southwest Vermont, known for its blend of history, culture, and the arts. Founded in the mid-18th century, the town's rich past is well-documented at the Bennington Museum. This venue displays a dynamic collection of art and history exhibits, including the most extensive collection of paintings by Grandma Moses. The Madison Brewing Company Pub & Restaurant welcomes newcomers to taste the region's craft beers in a relaxed, family-owned establishment.
Elsewhere, the "Old First" Congregational Church is a notable landmark in the historic downtown district. Built in 1805, it is Vermont's first Protestant church and holds a significant place in Bennington's history.
Brattleboro
Set on the picturesque confluence of the Connecticut River and West River, this Windham County municipality houses a lively arts community and a storied literary heritage. Several galleries line the main thoroughfare, serving as a go-to for art connoisseurs in Battleboro. You can walk into the Gallery in the Woods to inspect a world-class collection of fine art, folk art, jewelry, and other art forms sourced from the region and worldwide. The Stone Church hosts engaging live music events in a repurposed Victorian Gothic church with terrific acoustics and rustic decor.
Meanwhile, silver screen enthusiasts constantly congregate at the Latchis Theatre. This antique art deco building screens first-run movies on its four screens. The facility also stages special events and live performances.
Rutland
This hidden gem, about 35 miles from the New Hampshire state line, boasts a vibrant downtown district with many attractions. Highlights include the Chaffee Art Center, a gorgeous Queen Anne mansion completed in 1895. The building preserves regional heritage while promoting the arts through workshops, classes, and exhibitions. It also hosts two annual Art in the Park Festivals, which attract thousands of attendees. Guests can enjoy family-friendly entertainment at Rutland Bowlerama, home to dozens of bowling lanes, an arcade space, a restaurant, and other amenities.
Alternatively, they can visit Stonehedge Indoor Golf to enjoy diverse fun activities in a one-of-a-kind establishment. It features indoor golf simulators, a corn hole, pool tables, a virtual shooting range simulator, and much more.
Burlington
Burlington earns its spot among Vermont towns with unforgettable Main Streets because of its unmatched downtown district. This bustling community on the eastern shore of Lake Champlain welcomes tourists to discover its vibrant hub, centred around Church Street Marketplace. This pedestrian-friendly corridor has a high concentration of restaurants, galleries, boutiques, shops, and more, making it a popular social hub. The area stands out for its historic architecture and regularly hosts popular festivals. Highlights for performance art lovers include the Vermont Comedy Club.
The venue is a staple for improv, stand-up, and sketch comedy performances that draw enthusiasts from all over. Meanwhile, the Flynn showcases alternative performance art, featuring dance, readings, and musical shows in a 1930 facility.
Montpelier
Despite being the state capital, Montpelier has a charming small-town flair. With a population under 10,000 and a pedestrian-friendly town square hosting well-preserved historical structures, there is no shortage of highlights along the main thoroughfare, and the Savoy Theater is among the most prominent. Housed in a historic venue, the Savoy showcases the latest films and serves patrons delicious popcorn and wine. Additionally, the Lost Nation Theater is known for hosting engaging live performances in a welcoming atmosphere, including plays, musicals, and concerts.
The corridor also hosts several galleries, but Artisans Hand Craft Gallery is arguably the most impressive. Over 100 artists showcase their works at this quaint studio, culminating in a broad selection of art forms, from jewelry and glass to pottery and prints.
Waterbury
Waterbury is a lovely town in central Vermont with a walker- and bike-friendly downtown area. Its social hub revolves around the Waterbury Village Historic District, home to an eclectic blend of restaurants, boutique shops, antiques stores, and eateries. The Village Market of Waterbury provides natives and foreigners with all their grocery needs. This lively market sells everything from baked goods, farm produce, fresh meats, and other products, resulting in a popular gathering spot.
When you need something for your stomach, consider popping into Prohibition Pig for delicious smoked meats. Later, you can stop by Big Tree Brewing Company to down the food with tasty, locally produced beers. The cozy venue has an upbeat atmosphere, and receptive patrons are always ready to converse.
Winooski
This easygoing borough is home to the Community College of Vermont and is known for its infectious youthful energy and vibrant bar and restaurant scene. Walking down Main Street, you will come across several entertainment joints, with beer lovers gathering inside Four Quarters Brewing to enjoy great-tasting beers crafted from local ingredients. Foodies will relish sampling Winooski's captivating flavors, including the internationally inspired dishes at Tiny Thai Restaurant. This romantic location serves authentic Thai cuisine, such as chicken pad Thai and drunken noodles.
Meanwhile, those who explore the local nightlife can find delightful after-hours hangouts like Mule Bar. It has comfortable outdoor seating and offers a broad selection of alcoholic offerings. Alternatively, check out The Monkey House, known for its fantastic cocktails and soothing live music.
Newport
Newport's charm lies in its waterfront downtown district, which allows you to explore local attractions at a snail's pace while enjoying storybook water views. Some of the main stops along Main Street include the MAC Center for the Arts, a hub for crafters, artists, authors, and live performers. Additionally, Tavern on the Hill is where guests enjoy a hearty meal whenever they feel ravenous. The quaint diner serves delicious American fare alongside beers and cocktails.
Finally, those who simply want a chill outdoor spot to unplug can bask in the serene atmosphere of Pomerleau Park. It presents picnic spaces overlooking the lake and a scenic boardwalk with unmatched water panoramas.
Shelburne
Situated on the scenic shores of Lake Champlain, just seven miles from Burlington, Shelburne is known for a mix of attractions, including a heritage dating back to the 1700s. You can discover exciting stops along Main Street, such as Fiddlehead Brewing Company. This is tailored for those craving a tasty selection of locally crafted draft beers. But if you prefer an alternative alcoholic offering, you can head to Shelburne Vineyard. The establishments produce sweet-tasting Vermont wines and ciders, from classic to modern varieties.
If you visit with kids, you can take them to the Vermont Teddy Bear Factory to snuggle with life-size stuffed bears. Alternatively, they will enjoy sorting through cute gift items at The Country Christmas Loft, such as lighting, furnishing, linens, and homeware accessories.
Brandon
Nicknamed " the art and soul of Vermont," Brandon is a charismatic village in Rutland County with a bustling arts community. Its downtown region is jam-packed with galleries and restaurants. The Brandon Artists Guild showcases works by at least 30 regional artists. At the same time, 22 Park Eatery welcomes guests to try out local delicacies in a family-friendly spot in the heart of downtown. After a sumptuous meal, Ripton Mountain Distillery lets you down the food with crisp spirits.
Meanwhile, history lovers will enjoy visiting the Historic Sanderson Covered Bridge, a picturesque landmark from the 19th century. The structure straddles Otter Creek and offers a glimpse of old-world engineering and craftsmanship.
The Green Mountain State has a rich supply of small towns throughout its territory, demonstrating authentic New England charm and rich rural heritage. Whether visiting for the first time or returning for unfinished business, the downtown areas are the best place to begin exploring. From the vibrant watering holes and trendy restaurants in Winooski to the gorgeous old-world architecture in Montpellier, the Vermont towns with unforgettable Main Streets are a terrific reflection of the state's diversity.
