1. Where to Stay
Retreat to the bed-and-breakfast on eleven-acre Spirit Hill Farm (from $179), where windows overlook llama pastures, breakfast eggs come from the coop, and the smell of roasting granola wafts through the house. Each of the four wood-timbered suites is distinctive: There’s a private deck in the Garden Suite and the airy Sunrise Suite, opened last year, has its own sitting room.
Spot ruby-throated hummingbirds and purple finches in the riverside gardens behind Forty Putney Road (from $159), which abuts the 3.5-acre Hogle Wildlife Sanctuary. A few blocks from the center of town, the manor-style inn features six rooms outfitted with leather furniture, hot tubs, and fireplaces, and serves a complimentary two-course breakfast featuring local Mocha Joe’s coffee and True North Granola.
Sleep in a former tavern at the Whetstone Inn, part of the cluster of buildings that make up the tiny colonial town of Marlboro, just outside of Brattleboro. Antiques and locally produced crafts decorate eleven spacious rooms (doubles from $70), which are stocked with books rather than televisions, and the forested grounds include a pond for summertime swims.
2. Where to Eat
Reserve in advance for dinner at 20-seat TJ Buckley’s, housed in a vintage Worcester diner and run by chef Michael Fuller, a local pioneer in seasonal cooking since he opened the restaurant 29 years ago. The small menu changes daily based on market availability, but recent ingredient-driven dishes included a smoke trout tartlet ($10) and stuffed rabbit loin ($40) cooked in the open kitchen.
Watch the sunset from one of two large decks over the Connecticut River at newly opened Whetstone Station. The menu of creative takes on pub food—a chicken pretzel sandwich ($9), beer-braised short ribs ($21)—is complemented by more than a dozen craft beers on tap; in the fall, they’ll be rolling out their first brews made in-house.
Drive across the state line to Bernardston, M.A., to the Farm Table, inside a beautifully restored colonial house that’s more than 200 years old. Go for dinner, when the elegant space is illuminated by candles, and choose from garden-fresh items like asparagus-and-mushroom risotto ($20) and pizza topped with pesto and housemade lamb sausage ($14).
3. What to Do
Buy tickets in advance for the venerable Marlboro Music Festival’s weekend concerts (July 14 to August 12), held on the Marlboro College campus just outside of Brattleboro. Started in 1951, the annual camplike program brings together world-class instrumentalists from different backgrounds to reinterpret chamber works. Each week’s program is announced only a few days in advance, depending on which groups are deemed ready to perform, but all the concerts are uniformly impressive.
Time your trip to coincide with the first Friday of the month for the bustling Gallery Walk, when over 30 downtown spots keep their doors open into evening hours to host readings, live music, and artist receptions. Be sure to stop by Vermont Artisan Designs to pick up local crafts like Alan Stirt’s wooden bowls, and the more international Gallery in the Woods, which showcases surrealist work.
Check out the smart, eclectic variety of exhibits at the Brattleboro Museum and Art Center ($8 for adults), whose mission is to present shows that challenge the status quo. Housed in a former train station built in 1915, the museum hosts regular lectures and film screenings; current exhibits include John Gerding’s woodstack sculptures (through October 21) and an interactive area where visitors can create and exhibit their own collages (through March 2, 2013).
4. Insider’s Tip
Whetstone Ledges Farm operates a summer stand hidden a mile down a dirt road from Route 9, where you can pick up unique goods like dandelion marmalade and sparkling rhubarb chutney, not to mention wood-fired Vermont maple syrup ($5 for a half-pint) that’s cheaper than you’ll find elsewhere. Go on a Sunday morning, when locals arrive between 9 and 10 a.m. for coffee, freshly baked berry scones, and a game on the ping-pong table.
5. Oddball Day
Hop on a cycle to explore the lush countryside surrounding Brattleboro. Pick up your ride at Brattleboro Bicycle Shop, where you can rent a hybrid, helmet, and lock for $25 a day (book in advance—there are only ten available). Then go west about fifteen minutes to the Brattleboro Farmers’ Market (9 a.m. to 2 p.m., every Saturday through October 27), a leafy gathering spot with more than 50 food and craft vendors, picnic tables, and live music. Fill up on a honey custard bun ($2.75) from Wild Flour Vermont Bakery or a variety of steamed bites from Dim Sum Tea House before picking out supplies for lunch, like a wedge of Vermont Shepherd’s Invierno, a cheese made with a blend of sheep and cow milk ($20 per pound). Once you’ve finished shopping, head back downtown on scenic Route 30, which runs along the West River and has a wide shoulder to accommodate bikers. Keep an eye out for groups of cars parked along the side of the road, often a sign there’s a swimming hole nearby. You’ll find a quiet one if you turn down Stickney Brook Road, about six miles from downtown, where Old Jelly Mill Falls offers a series of shallow pools and large slabs of rock that work well as picnic tables. Afterward, head another six miles up Route 30 to explore colonial Newfane, a picturesque town where a columned courthouse, high-steepled church, and clapboard houses sit around a village green. Stop by Dutton Berry Farm (open 7 a.m. to 7 p.m. during summer) to pick your own blueberries, raspberries, and blackberries. Pedal back to Brattleboro, return your bike, and grab a booth at the Chelsea Royal Diner, which dates to 1938, for Saturday’s blue-plate special of chicken-fried steak with country gravy ($10.50) followed by a banana split with homemade ice cream ($4.50). Finish off the day with a pint ($5) at McNeill’s Pub, which exclusively serves the sixteen craft brews produced at McNeill’s Brewery in town.
The Brattleboro Chamber of Commerce is the most comprehensive tool for reading up on everything the town has to offer.
Find local events and the winners of “Best of Brattleboro” awards at Brattleboro Reformer.
The Windham Regional Commission offers detailed biking maps of southeastern Vermont.
Research other regional attractions and plan side trips at Vermont’s official tourism site.