This Vermont Town Has The Most Walkable Downtown

When it comes to walkable downtowns in Vermont, there is no place quite like Middlebury. Combining the compact selection of shops, eateries, and attractions in a handful of city blocks is one thing, but merging that with the beating pulse of an active college campus creates a dynamic that visitors cannot find elsewhere in the state. Like many New England communities, Middlebury has a history worth exploring and appreciating, making it a pleasant addition to the region's natural attractions. Many find the town on their sightseeing of Lake Champlain and the Green Mountains, but end up staying longer to explore downtown Middlebury on foot, as it was meant to be.

A Walkable Layout

Running the length of Main Street and Merchants Row, the downtown business area loops around, folding in Court and Seymour Streets while circling the Village Green. A footpath crosses Otter Creek via a bridge, linking Mill Street back into town near the rushing falls. Walkers can actually see the Otter Creek waterfall from several different vantage points. Middlebury College sits on the edge of the walkable downtown, so the campus’s art galleries, live productions, and community events are a short trek away.

Standing just steps from Middlebury’s central district, the Swift House Inn is a standout choice for locally owned accommodation downtown. Built in 1814, it eventually became the home of Vermont governor John W. Stewart. Spread across three old structures on four acres of landscaped greenery, twenty guest rooms offer comfort enhanced by features such as in-room fireplaces and bathtubs. Just outside the front door, a path leads to the Trail Around Middlebury, which connects a guest to Middlebury College in a short 15-minute walk. Jessica's at Swift House Inn has earned Wine Spectator’s Best of Award of Excellence - shared by only two other Vermont dining spots.

Dining Downtown in Middlebury

On the corner where Main Street meets the Cross Street Bridge, Two Brothers Tavern has been serving guests since 2002. Located right in the heart of Middlebury’s walkable downtown area, it has been successful by not having to be too extra. The whole vibe of this restaurant is comfort foods and hearty portions, so diners can expect everything from burgers and sandwiches to salads and changing daily specials. Be advised that the location is not open on Wednesdays.

When visitors explore closer to the river, they can find the Marble Works, a repurposed factory building that now houses multiple stores and eateries. Inside, you can find one of the most popular places for a quick bite in Middlebury, even recommended by the folks at the Swift House. The American Flatbread is known for its handmade wood-fired oven, which turns out flatbreads made mostly from nearby farms. They add information about which ingredients were sourced locally to their daily menu. This popular eatery is only open Wednesday through Saturday, 4:30 to 9, so plan accordingly.

Shopping Downtown

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Opened in 1949, the Vermont Book Shop has been a prominent downtown fixture for decades. One of New England’s oldest independent bookstores, it has changed little in its look or operations over the years. The interior of the shop was modernized as needed, yet it still created a welcoming and charming atmosphere that inspired readers to take time with the staff to find their next favorite read. The store helps bring authors to the city, even when they host their events through Middlebury College, which the Vermont Book Shop supports by offering on-site selection of faculty and alumni-authored works.

Souvenirs are such a critical part of traveling for many that locations like Sweet Cecily at 42 Main Street are a gem to find. The team here calls themselves a ‘modern country gift shop,’ and that could be a good way to describe the eclectic assortment of Vermont-made products, crafts, and décor. While the products can change regularly, this gift shop is sure to have one-of-a-kind items, from handmade soaps to locally made pine tree mugs, all perfect for memorializing a trip to the Green Mountains.

Nearby Towns Worth Exploring

Vergennes sits about fifteen miles up Route 22 from Middlebury - this place earned its title as Vermont’s first chartered city back in 1788. On Main Street, you can find the Vergennes Opera House, built in 1897, which keeps entertainment close for guests and locals through theater, music, and local gatherings. The town also has a compact shopping and dining area, similar to Middlebury, with popular retail locations such as Diddle & Zen for home goods, beauty products, and bouquets.

Head east for roughly twelve miles and reach Bristol, which offers appeal through two attractions worth planning a visit around. Not far from the downtown portion, drive just two miles along Lincoln Road to find Bartlett Falls, sometimes locally called Bristol Falls. This natural attraction drops fourteen feet into cool pools below, and the deep pools here become a coveted swimming destination in the warmer months. The other attraction here is the community's quaint, simple layout, brought to life by popular eateries like the locally owned and operated Bobcat Café. The menu is not vast, showing that doing a few things excellently beats doing many things just okay; standouts here include flavorful choices like the Chicken Tinga Enchiladas or the Pear & Gorgonzola Salad.

Headed north roughly 35 miles, Burlington is another location in the state with a quaint community center, Church Street Marketplace. This destination is a stretch of four blocks, exclusively designed for walking, filled instead with small stores, eateries, cafés, and performers who appear throughout the year. From that central hub, it's possible to walk directly onto the Burlington Waterfront Trail, which follows the edge of Lake Champlain for 7.6 miles. Located right on the shore, the ECHO Leahy Center brings together aquatic displays, scientific exploration, and hands-on learning focused on the lake's natural systems and the nearby landscapes.

Middlebury proves its claim to being Vermont’s most walkable downtown when someone takes the time to set out on foot and explore the compact collection of city blocks. Spread tightly around the Village Green and Otter Creek, the town’s best restaurants and shops are no more than four blocks apart. Instead of treating sidewalks as an afterthought, the layout prioritizes them, shaping movement around walking rather than driving. Lodging fits seamlessly into this pattern, as the Swift House Inn places visitors right in the flow, with direct access to a trail that leads to the lively downtown. Best of all, Middlebury is conveniently located to explore nearby historic and cultural centers in Vermont, like Burlington and Bristol.