Brattleboro, VT

BEST WEEKEND TO GO: June 5-7

DISTANCE: 201 mi – about 3 hours 34 mins (up to 4 hours 10 mins in traffic)

WHY GO: Southeastern Vermont’s Brattleboro may not have much in common with Pamplona, Spain, but in 2001 the towns became sisters of a sort when New Yorker–turned-Vermonter Orly Munzing pulled off Brattleboro’s first Strolling of the Heifers (strollingoftheheifers.com), a ladylike riff on the testosterone-charged Running of the Bulls that she dreamed up to promote and save local farms. Arrive by 5:30pm Friday and you can enjoy the tastes and smells of the Great Vermont Grilled Cheese Cook-Off at the River Garden (153 Main St, 802-257-4886), a glass-enclosed downtown public space where amateurs and pro chefs vie for the Golden Spatula with creations made from Vermont cheeses and breads. Get downtown by 9am on Saturday to secure a good spot from which to watch the lovingly adorned heifers and their 4-H club-kid companions, as well as the Clydesdales, sheep, water buffalo, parade floats, locals and pooper-scoopers that follow them. (Dogs are strictly verboten.) The parade (10–11am) ends at the Brattleboro Common, where a Miss VerMOOnt contest judges the bovine gals in such categories as best dressed and best personality, and a celebrity milking contest features surprise guests and udders. On the nearby Brattleboro Retreat grounds, the fun breaks loose at the Dairy Fest & Marketplace, with a fiddlers’ tent, a petting zoo, craft tables, a kids’ entertainment station, live music, trapeze artists and, of course, a Vermont cheese pavilion. And you can always head back to the River Garden, where free Ben & Jerry’s ice cream is scooped all day. A contra dance at the Stone Church downtown (Grove at Main Street; 7–10pm, $6) awaits anyone with restless legs syndrome

WHY STAY: Don’t leave Sunday before you partake of the Royal Farmers’ Feast at West Brattleboro’s classic Chelsea Royal Diner (487 Marlboro Rd, 802-254-8399; $7.50); Organic Valley provides most of the fresh breakfast ingredients, and all proceeds go to Strolling of the Heifers’ educational fund. Pick up a map here of local farms that are open to visitors all day with hayrides and barn tours. You could also head up to Dummerston (20 minutes away) to have a peek at Naulakha (707 Kipling Rd, Dummerston, VT; 802-254-6868), the mansion Rudyard Kipling lived in for four years with his American wife, and in which he wrote The Jungle Book. (It’s available for weekly rentals year-round, but not open to visitors.)

WHAT TO EAT: Head to the Riverview Café (36 Bridge St, 802-254-9841; lunch $8–$15; dinner $15–$30) for an alfresco lunch or dinner of locally sourced foods—like cider-bourbon chicken, or butternut squash and spinach over basmati rice—overlooking the Connecticut River. The tiny cash-and-check-only TJ Buckley (132 Elliot St, 802-257-4922; entrées $40), housed in an ancient diner and featuring an open kitchen, has a verbal (and ever-changing) menu offering a choice of four entrées, two of which are seafood-based, with a focus on foods sourced within a 15-mile radius.

WHERE TO STAY: The Latchis Hotel (50 Main St; 802-254-6300, latchis.com; double $80–$160 per night), housed in an Art Deco landmark, is the most centrally located option. Several miles into the countryside is the Meadowlark B&B (13 Gibson Rd at Orchard St; 802-257-4582, meadowlarkinnvt.com; $160–$240 per night). Perched on top of a hill in the middle of nowhere, this place really feels like an escape. A less expensive alternative is the Super 8 Motel (1043 Putney Rd, 802-254-8889; double $90-$95 per night).

GET THERE: Renting a car and shooting up I-91 is your best bet: It’s faster by far than bus or train, and you’ll want a car while you’re there.

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