Five reasons to stop in Brattleboro

If you’re driving south on Interstate 91, Brattleboro is the last large town you pass on the way out of Vermont and the first one on the way back. With Marlboro College, the School for International Training nearby and the five colleges in the Northampton-Amherst area of Massachusetts to the south, Brattleboro invites a blend of back-to-the-landers, students, young professionals, artists and adventure seekers. No wonder Brattleboro is home to a thriving arts scene, a growing number of local restaurants and shops and a culture that’s entirely its own. Southeastern Vermont’s largest city is a great starting point for a weekend playing in the Connecticut River, the neighboring mountains on both sides of the river, or four ski resorts within easy driving distance.

  1. Hike to a View

For an easy hike within walking distance of downtown, head across the river to New Hampshire for a hike up the looming Mount Wantastiquet. Park behind the old Wal-Mart directly across the river and hike two miles up wide four-wheeler trail. At an elevation of 1,368 feet, the summit and nearby Miner’s Ledge offers stunning western views of the foliage of the Connecticut River Valley and looks down on downtown Brattleboro. You’ll be up and down in about three hours, in time for dinner and a movie at the classic Latchis Movie Theater.

For an extended hike, continue on the trail to nearby Indian Pond and the 488-acre Madame Sherri Forest. The forest near Chesterfield, N.H., was the site of former resident Madame Antoinette Sherri’s massive estate, where her raucous parties gained local notoriety. On October 18, 1962, the house was destroyed by fire and the ruins have sat empty since. The foundation, chimneys and a grand stone staircase are still standing, making it an intriguing and certainly spooky discovery during a foliage hike.

Other easy hikes include the Retreat trails, a network of 11 miles spreading all over town, used by everyone from local dog walkers to the high school cross country running team. Nearby Long Trail hikes include Southern Vermont’s tallest peak, 3,936-foot Stratton Mountain. The Long Trail leads 3.8 miles to the summit, which offers sweeping views from a fire tower. Extend your hike by continuing 3.2 miles to Stratton Pond and camp at the shelter or a primitive campsite on the northern shore. Return to your car in the morning by way of the 3.7-mile long Stratton Pond Trail.

  1. Ride with the West Hill Shop

Cyclists looking to push the pedals ought to drive the 15 minutes north to Putney for a visit to the legendary West Hill Shop, located just off the I91. In addition to rentals and full bike and ski fitting, the shop holds group rides every Tuesday evening with the Putney Bike Club through the towns of Putney, Dummerston, Saxton River, Chester and Westminster followed by a BBQ back at the shop. Women’s rides are Wednesday evenings and longer gravel-grinding tours are on the second Sunday of every month, running from April until it starts to snow. Look for the red and gold jerseys and do your best to keep up.

For a scenic and easy mountain bike ride, head to the West River Trail, 16 miles of former railroad line open year-round to hikers, bikers and cross-country skiers. The southern portion runs 3.5 miles from the Marina trailhead near downtown and follows the West River north. For a slightly longer trip, leave your bike at the end of the trail and hike about a mile to the summit of Black Mountain for lunch.

For gear shopping, Sam’s Outdoor Outfitters has stood at its 74 Main St. Brattleboro location since 1932 when it started as an Army Navy surplus store. Today, the store has clothing and equipment for hiking, camping, hunting, fishing, running and more. Plus, the popcorn is always free. Burrows Specialized Sports and the Brattleboro Bicycle Shop both offer bike repairs, maps and friendly service.


  1. Stay at a Classic B&B

For camping close to town, reserve a campsite at Fort Dummer State Park. Located on 217 acres, the park has 50 tent sites and ten lean-tos with views of Mount Wantastiquet and local farms. It’s an easy downhill bike ride into town for supplies. If you’re a cat person, check into The One Cat, a cozy bed and breakfast close to downtown owned and operated by Pat Sheehan and Conrad Feinson. The Brighton and New England rooms make for an exclusive getaway with a delicious breakfast and two very friendly cats ($132 – $165 per night). The Crosby House, also close to downtown, offers three rooms and two suites, maintained in the same genteel style it had when it opened in 1868 ($160 – $195 per night).

  1. Paddle the Connecticut

For paddling trips of a day or longer on the Connecticut River, consult the Connecticut River Paddlers’ Trail, a network of primitive campsites and access points that stretch from the river’s headwaters all the way south to Long Island Sound. For a full day’s paddle, launch north of Brattleboro in Bellows Falls (25 miles) or Putney (16.7 miles) and follow the river south, finishing at the Retreat Meadows. A full list of access points and maps is available at

If gentler paddling is what you seek, head to the Retreat Meadows, located within driving distance of downtown. Rent canoes from the Vermont Canoe Touring Center and paddle around to bird watch or cast a line for bass. You’ll have views of the Brattleboro Retreat, the historic Harris Hill Ski Jump and the Retreat Tower, constructed by patients in 1887. After an afternoon on the water, head to the Marina right on the water for seafood and other American fare or the Top Of The Hill Grill for hickory smoked brisket ribs, pulled pork and more.

  1. Savor the Local Brews

Start your day with coffee and scones from Mocha Joes. This subterranean café on Main Street is a Brattleboro institution and a great spot to read the paper, people-watch, or just grab your coffee and go. For picnic fixings, swing by the Brattleboro Food Co-op or the Brattleboro Farmer’s Market (held every Saturday morning) for all your natural and organic needs. After a full day outside, Brattleboro’s downtown offers plenty of food and drink options. For a burger and a beer before or after a movie at the Latchis next door, the Flat Street Pub is an easy pick for pub fare. The Whetstone Station has great view of the river, a full menu of American cuisine and a long beer list that includes their own experimental house-brewed beers. At Fireworks, try a brick oven pizza with pulled pork, broccoli rabe, Kalamata olives, sweet red pepper and onion, gorgonzola and mozzarella and a signature cocktail like the Payback, jalapeno infused gold tequila with muddled kiwi, agave nectar, triple sec and fresh lime.

In recent years, Brattleboro has jumped into the brewing and distilling scene with a few notable successes. North of downtown, Saxtons River Distillery distills Sapling maple liqueur, bourbon, rye and Perc Coffee Liqueur. Downtown, step into the cozy, wood-paneled tasting room of the Hermit Thrush Brewery on High Street for a tasting of some imaginative Belgian-inspired ales brewed by Christophe Gagné and Avery Schwenk. Leave with cans or a growler of the signature Brattlebeer, a sour ale blended with cider for a slightly tart flavor with fruit and malt undertones, or the Brooks Brown, a rear-round favorite with a deep nutty and roasted malt flavor named for the iconic Brooks Building located just across the street.

Photo courtesy of Strolling of the Heifers.

Evan Johnson

Evan Johnson is the staff writer for Vermont Sports Magazine. The native Vermonter enjoys steep and deep skiing and wandering all over the state by Subaru. Find him on Twitter at @evanisathome.

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