8 Picture-Perfect Main Streets In Vermont
There’s something quite romantic about the slower side of Vermont. Outside the bigger cities are small, delightful towns where a stroll down Main Street feels like walking inside a Hallmark movie. It’s where you can grab a cup of coffee and take a walk through an idyllic city park, or just window shop down streets that smell of fresh pastries. It’s where an afternoon may lead you to a hidden book shop, antique store, or your new favorite diner. So, let’s get ready to explore these picture-perfect main streets of Vermont.
Bristol
Nestled in the Green Mountains in eastern Vermont is Bristol, a small town with a big heart. Main Street is quintessentially New England, with post offices that look like small cottages, and white church steeples piercing the sky. In the heart of Bristol is the Bristol Town Green Playground, with playground equipment for the little ones, and long sidewalks with benches where you can slow down for a moment. It’s home to cozy bookstores like Recycled Reading of Vermont Books & Instruments, and friendly neighborhood taverns like South Mountain Tavern.
The perfect day in Bristol consists of exploring Main Street and then venturing slightly outside of town to Bartlett Falls. No matter what time of year you visit Bartlett Falls, the views are spectacular. It’s especially fun in the summer, when you can swing from rope swings into the New Haven River, or explore the cave behind the 15-foot waterfalls. It’s the perfect place to explore and take in the unique views of the Green Mountains in Bristol.
Stowe
North of Montpelier is Stowe, a small community hidden away in the Green Mountains of northern Vermont. Your map may call the central street in Stowe Vermont Route 100, but the locals just call it Main Street. It is a delightful walkable area, with cottage-like buildings scattered along brick sidewalks and inviting storefronts like Lake Champlain Chocolates. The Stowe Village Historic District (which occupies much of Main Street) highlights the Greek-Revival architecture of Stowe.
The best example of the architectural elegance of Stow is the Green Mountain Inn. It was built in 1833 and is still open for business! The rooms of the inn reflect the trends of the 1800s, while still offering modern amenities. And if you aren’t planning on staying the night (although you should!), you can grab a meal or a cocktail in their amazing dining room. One of the best ways to experience the true heart of Stowe is to swing by Shaw’s General Store. It has a little bit of everything, and the vibes feel like a throwback to simpler times.
Brattleboro
On the southern edge of Vermont near the New Hampshire border is where you’ll find the small city of Brattleboro. Settled along the Connecticut River, the streets of Brattleboro are narrow and winding, with the Black Mountains dominating the skyline in the distance. Main Street, aka the Brattleboro Downtown Historic District, is a mix of architectural styles from the 1800s and 1900s. Expect opulent brick facades, manicured sidewalks, and delightful restaurants, like the Echo Restaurant and Lounge or the Works Café.
Brattleboro is also known for its fantastic art and music scene. The Latchis Hotel and Theatre is a hidden treasure, blending its Art Deco design with modern amenities. It has cozy rooms, a 750-seat historical movie theater, a live entertainment center, and a pub. Another surprising discovery in Brattleboro is the Stone Church. It opened in 1875 as a Unitarian church, but today operates as a thriving arts and music venue. It kept its Gothic Revival style, but traded in its collection plates and Sunday masses for lively indie concerts and community events.
Manchester
In southern Vermont, not too far from the Green Mountain National Forest, is the sleepy town of Manchester. The community feels part idyllic mountain resort, part sleepy New England village. The buildings are brightly painted, with tall clock towers and church steeples in the shade of the Green Mountains. It’s where you can shop at cozy bookstores like the Northshire Bookstore, and then grab a bite to eat at a former library turned restaurant at The Silver Fork.
It’s easy to lose track of time exploring all of the wonderful shops and taking in the scenery of the Manchester Village Historic District. But if you wander just a little south of central Manchester, you’ll discover the stunning and historical grounds of Hildene, the Lincoln family home. It was built in 1905 by Abraham Lincoln’s only surviving son, and is a breathtaking estate with picturesque gardens surrounding a restored Georgian Revival mansion.
Waterbury
Waterbury is the type of town that is a foodies paradise. Nestled in northern Vermont, northwest of Montpelier, Waterbury is New England charm at its finest! There are so many tasty restaurants scattered on West Main Street that it’s hard to narrow it down to just one. For top-knotch fine dining, there’s Hen of the Wood, or if you’re into fun and funky stops, the Prohibition Pig is a local favorite. Or if you’re into seafood and late-night drinks, the Salt and Rind is a great option!
Waterbury’s biggest claim to fame isn’t its cocktails or fine dining, but its ice cream! As home to Ben and Jerry’s Ice Cream, you can visit the only factory that is open to the public. You can sample flavors, stock up on ice cream, or take a tour of the factory. The Ben and Jerry's Flavor Graveyard is a must-see, where you can take an outdoor tour of all the strange flavors that didn’t quite make the cut.
Vergennes
As Vermont’s oldest city (founded in 1788), there’s a lot to love about Vergennes. Not only does it pack a powerful historical punch in its restored buildings, but its location along the banks of Otter Creek creates breathtaking New England vistas. A walk along Main Street provides views of the creek at Settlers Park. For a better view of the city, Vergennes Falls Park (located off Canal Street) provides a one-of-a-kind view of how Vergennes' buildings sit right on the water.
Traveling down Main Street from Settlers Park, there are many things to discover. You can grab a bite to eat at 3 Squares Cafe before catching a live show at the historic Vergennes Opera House. The opera house is a great example of the classic architecture of Vergennes. Built in 1897, it’s a community landmark hosting rotating events and local performances throughout the year. Vergennes may be one of the smaller towns on this list, but its history and beautiful main street make it well worth the trip!
St. Albans City
The hidden gem of St. Albans City is in the northern part of Vermont, not too far from the Canadian border. With easy access to the Missisquoi Valley Rail Trail and Lake Champlain, it serves as an idyllic escape into the beautiful scenery of Vermont. But while outdoor adventure awaits in St. Albans City, the picture-perfect Main Street steals the spotlight.
The intersection of North and South Main Street captures the soul of St. Albans City. It is where you can relax at Taylor Park, a dedicated green space that feels like walking inside of Stars Hollow. With ornate bronze fountains, winding pathways that put the Greek Revival architecture of the town on full display. You can walk from the park to the Catalyst Coffee Bar for a cup of coffee, then north to the Eloquent Page to shop for used or out-of-print books.
Bennington
Tucked away in the southern corner of Vermont, near the New York border, is Bennington. A picturesque community that seamlessly blends its rich history with fun, modern vibes. The corner of Main Street and North Street is Bennington’s central hub, with unusual surprises like Lil' Britain (where you can dine on classic British comfort food) or the local favorite, Madison Brewing Company Pub and Restaurant.
While it’s easy to spend an entire afternoon strolling down Main Street, there’s also a historical side to Bennington. Its crown jewel, located to the west of town on the tail end of Main Street, is the Bennington Battle Monument. The monument commemorates the Battle of Bennington, a battle that turned the tide in America’s favor in the Revolutionary War. Standing over 300 feet tall, it’s the largest structure in the state of Vermont and is a must-see in the area. When you want to learn more about the monument, there’s a small visitor’s center and museum at the base of the monument.
Discover Vermont’s 8 Most Delightful Main Streets
There’s nothing cookie-cutter about these unique Vermont towns. While they deliver that unmistakable New England charm with white church steeples and vibrant fall foliage, there’s something unique about each of these little villages. Whether it’s the Art Deco vibes of Brattleboro or the mountain resort vibes of Manchester. And after a day of exploring, there’s always a park or stunning mountain trail just outside the city limits. So when you’re ready to get lost in the hidden pockets of Vermont, these charming towns are sure to win over your heart.
