72 Hours on Vermont’s Route 30
Arts, Eats, and Scenic Views
Road tripping through the Southern portion of Vermont’s idyllic Route 30 reveals a landscape shaped by both tradition and imagination. Stretching from the arts-infused riverside town of Brattleboro up through the Green Mountain foothills to Dorset, this winding rural road runs through a region where creativity and community go hand in hand.
Small-town galleries showcase experimental work alongside traditional crafts, historic cinemas glow with marquee charm, and family-run cafes double as hubs for progressive food culture — all set against the backdrop of rolling hills and forested valleys.
More than a scenic drive, Route 30 stitches together some of Vermont‘s most inviting destinations, and three days will leave you feeling utterly charmed.
DAY ONE
Brattleboro
Kickstart your Route 30 road trip in hilly, historic Brattleboro, an arts-forward town with an undeniably scenic setting. Map out a self-guided art walk by touring the town’s many galleries and institutions. Start at the Brattleboro Museum & Art Center, set in the town’s repurposed train station and featuring rotating shows by local and international artists. On Main Street, Gallery in the Woods and Vermont Artisan Designs display a mix of fine art and handcrafted works across a variety of media. Be sure that Fire Arts Vermont makes it onto your itinerary, too. Watch as glass artists work on the fiery craft of glassblowing in the gallery and studio space two miles from downtown Brattleboro.
An early adopter of the farm-to-table movement, Brattleboro’s culinary roots run deep. Grab picnic supplies at the Brattleboro Food Co-op on Main Street or relax in its cafe over a locavore lunch. By the bridge, Superfresh! Organic Café serves vegan raw dishes like superfood-spiked juices, a beet-based chocolate cake, and nutrition-packed salads and bowls. Nearby, Vegan A.F. is set in a carriage-like room and also has outdoor seating where you can enjoy creative, vegan twists on classic dishes.
Explore Vermont’s Route 30
The southern portion of Vermont’s route 30 connects Brattleboro and Dorset, inviting exploration. A road trip along the route’s southern portion with Mirna Valerio, aka @themirnavator, reveals postcard-worthy landscapes and downtowns bustling with art and innovation.
For those looking beyond plant-based plates, Brattleboro’s dining scene widens into a mix of cozy institutions and elevated kitchens. From the comfort of a Worcester-style dining car, TJ Buckley’s Uptown Dining serves fish and meat dishes with the freshest of veggies. The New England House is a go-to any time of day, with equally hearty breakfast, lunch, and dinner options. The oyster bar at Peter Havens Restaurant is a highlight of its seafood-centered menu, while Kipling’s Tavern serves comfort food in a pub setting. At Cai’s Dim Sum, the art of small plates intersects with actual art: delectable dim sum pairs with multimedia displays in the restaurant’s CX Silver Gallery.
Finish your day in Brattleboro with a movie on Main Street at the onsite theater at the Latchis Hotel, an Art Deco hotel dating to the 1930s. For another unique stay, book Naulakha, designed by author Rudyard Kipling in the rural hamlet of Dummerston, about a 15-minute drive from downtown Brattleboro. Kipling wrote The Jungle Books here, and today the National Historic Landmark’s house and carriage house can be rented as vacation homes, with interiors preserved much as the Kiplings left them. The house stands beside the historic Scott Farm Orchard, home to heirloom apples and Stone Wall Park, where you can experience the traditional craft of dry stone walling.
DAY TWO
Newfane and Townshend
From Brattleboro, Route 30 snakes its way north past bucolic scenes and historic covered bridges. Three notables are the Dummerston Covered Bridge, one of Vermont’s longest; the stately Scott Covered Bridge in Townshend; and the charming Jamaica Island Covered Bridge, which is tucked along the West River.
As you’re driving these winding roads, veer west to explore Stratton’s art galleries. The Stratton Vendors Village is held on summer weekends in the Village Courtyard of the Stratton Mountain Resort, a premier Vermont ski and snowboard destination that delivers four-season recreation. It features work from local crafters and artists, along with some tasty baked goods and other edible treats. For a bite elsewhere, pick up some maple products and smoked meats at Lawrence’s Country Store in Townshend, or settle in for a meal. Two standout choices are Honeypie in Jamaica — home of loaded burgers, sausages, sandwiches, and shakes — and Fat Crow Restaurant in Newfane, whose menu ranges from small plates like steak tips and steamed mussels to entrees like an 18-ounce ribeye. Both support local farms and serve local foods.
In the foothills of the Green Mountain National Forest, hikers of all levels will find plenty of trails to explore. Townshend State Park, set beneath Bald Mountain and not far from the historic Scott Covered Bridge, presents wooded paths that climb to rewarding viewpoints, along with shady campsites for overnight stays. A short drive north, Jamaica State Park spreads along the West River, where a flat riverside rail trail makes for an easy walk or bike ride; more challenging routes lead up into the surrounding hills. The park is also known for Hamilton Falls, a dramatic 125-foot cascade tucked deep in the forest, and provides peaceful camping options for those looking to linger in the scenery.
For brick-and-mortar lodgings, The Newfane Inn, set in its namesake hamlet, and the elegant Windham Hill Inn in nearby Townshend both offer individually styled guest rooms and exceptional dining. Each inn highlights seasonal local produce, with dinners that showcase Vermont flavors and breakfasts that make for a memorable start to the day.
Day three
Manchester and Dorset
Farther northwest on Route 30 meanders through a region delightfully dubbed The Shires. Here, the Taconic (to the west) and Green (to the east) mountains meet, all overlooked by the highest peak of the Taconic range, Mount Equinox.
Manchester is a hub of culture and commerce. It’s a town of two parts: Manchester Village and Manchester Center. The latter is a bustling retail area known for its designer outlet stores. Woven between those stores are art galleries and artisan craft shops like the Vermont Bowl Mill, featuring exquisitely turned wooden bowls and vases, and Epoch Artisans Gallery, where local artists show off their stunning work. At Manchester Hot Glass, visitors can learn glassblowing and make their own glass art to take home.
And no trip to Manchester is complete without browsing the family-owned Northshire Bookstore, which hosts local events and serves as a community gathering place in addition to selling new, used, and rare books.
Earth Sky Time Community Farm near Manchester Center blends music with rural scenery in its summer-long concert series, serving drinks and farm-fresh baked goods alongside the performances. Situated on 100 acres, the Southern Vermont Arts Center brings art into nature, with a permanent indoor-outdoor collection and rotating exhibits across its galleries and sculpture garden.
In Manchester Village, tour Hildene, the Gilded Age estate of President Abraham Lincoln’s son Robert, set on more than 400 acres of grounds and open to visitors year-round. Nearby, the Wilburton Inn — a 1902 mansion turned resort cocooned in mountain greenery — houses the Museum of the Creative Process, with large-scale sculptures scattered across its sloping lawns. Back in the heart of Manchester Village, the museum’s gallery displays additional works, including a collection by New York figurative expressionist painter Henry Gorski.
On Main Street, the Equinox Golf Resort & Spa holds court. Though greatly expanded in the subsequent centuries, the property’s roots date to 1769 when it stood as the modest Marsh Tavern. Today’s terraced Marsh Tavern is a great stop for lunch or dinner, or you can try Equinox’s intimate Chop House. In Manchester Center, Mother Myrick’s homemade pies and signature buttercrunch have been tempting passersby since 1977. Depot 62, a Middle Eastern restaurant set in a furniture store, and Thai Basil add international dining options.
Continuing northwest along Route 30 to Dorset, there’s more local flavor at the Dorset Union Store. Founded in 1816, it’s one of Vermont’s oldest country stores and still fuels locals with pies, sandwiches, and soups. Slightly “younger,” the H.N. Williams Store, a nostalgic-feeling general store dating to 1840, has everything from toys and hardware to a deli counter and cafe. Nearby, Dorset Bakery tempts with fresh, flaky pastries, as well as full breakfast and lunch menus if you’d like to stick around for a full meal.
Settle into one of Dorset’s many inns, such as The Dorset Inn, which dates to 1796, or Barrows House Inn & Restaurant, a compound of eight buildings on six acres. Accommodations range from suites with whirlpool baths and fireplaces to multi-room cottages.
Wherever you stay, eat, and play, Route 30 invites you to come for the arts, crafts, food, and views — and promises to leave you with memories shaped by Vermont’s rich character.