52 Best Weekend Trips and Getaways from Boston

Outdoor Adventures

weekend trips getaways boston massachusetts new england


1. Peak’s Island, Maine

Two hours by car

Different Strokes | If the idea of wearing a tank top seems profoundly depressing, skip the sports club in favor of an upper-body workout that’ll replace the reflection in the gym mirror with a view of Maine’s wild and rocky coast. And thankfully, there’s little exertion in getting there. Drive up Friday night; stay at Portland’s Regency Hotel (two hours from Boston); then catch the nearby ferry at 9:15 a.m. to Peaks Island, where the affable staff of Maine Island Kayak Company will escort you to a kayaker’s paradise. After an introductory paddling course, a primer on the vagaries of ocean weather, and some disclaimers, you’re ready to slide into a single-person sea kayak and head for open water. You’ll first need to get your heading: Peaks Island, just off Portland’s coast in Casco Bay, is one of the area’s dozens of small islands, many of which are public. Some feature Civil War–era forts, sea birds, and coastal flora and fauna. Expeditions are led by registered Maine guides—in other words, experienced outdoorspeople who know their way around a compass and can handle almost anything Mother Nature tosses their way. Although the company does offer half-day excursions (sans meals, $65 per person), we recommend a full-day jaunt ($115 per person), which allows plenty of time to practice maneuvering. Meanwhile, if you’ve already got kayaking chops and want to spend as much time near the water as possible, opt instead for the two-night camping trip.

Maine Island Kayak Company, Kayak Beach, Peaks Island, Maine, 207-766-2373, maineislandkayak.com. Stay: Portland Regency Hotel, 20 Milk St., Portland, Maine, 207-774-4200, theregency.com.

2. Stowe, Vermont

Three hours, 45 minutes by car

It’s All Downhill | Singing, dancing, precious urchins mugging for the camera…and yet, you don’t see much mountain biking in The Sound of Music. But the state-of-the-art trails at Stowe’s Trapp Family Lodge (owned and operated by the movie’s same family) make the hills come alive—with the grunts and groans of cyclists testing their mettle on more than 25 miles’ worth of track.

700 Trapp Hill Rd., Stowe, Vermont, 800-826-7000, trappfamily.com.

3. Lake Champlain, Vermont

Three hours, 45 minutes by car

Peak Experiences | You’ve seen fall foliage from the car, the hiking trail, and the boat—now how about from the sky? Parafly Paragliding offers classes in the Lake Champlain valley; on a cloudless day, you’ll get 360-degree views of the fiery sugar maples stretching clear to the northern border.

116 Waybury Rd., Colchester, Vermont, 802-879-3507, paraflypg.com. Stay: Willard Street Inn, 349 S. Willard St., Burlington, Vermont, 802-651-8710, willardstreetinn.com.

4. Craftsbury Common, Vermont

Four hours by car

Cause A Row | The Craftsbury Outdoor Center almost kisses Canada, but it’s still close enough for a two-day escape. The rustic resort sits on a long, narrow lake surrounded by farmland, and is the perfect place to explore the rarefied world of sculling. Craftsbury offers intensive, all-inclusive weekend programs for every level, some of which come with yoga classes. Bonus: It also rolls out running camps, and has arguably the finest cross-country skiing trails in New England.

535 Lost Nation Rd., Craftsbury Common, Vermont, 802-586-7767, craftsbury.com

5. Charlemont, Massachusetts

Two hours, 45 minutes by car

See the Forest for the Trees | Zipline tours got their start in Central America in the 1970s, but it’s only been in recent years that they’ve hit New England in a big way. Most are in the northernmost part of the region, though two Charlemont-based companies are competing to be the go-to source in Massachusetts. Zoar Outdoor Canopy Tours emphasizes the educational aspect, with guides who describe the local foliage and fauna. Meanwhile, Berkshire East goes for the thrill, with two 2,000-plus-foot ziplines that plunge downhill at 50 miles per hour.

Zoar Outdoor Canopy Tours, 800-532-7483, zoaroutdoor.com; Berkshire East, 413-225-2425, berkshireeast.com. Stay: Warfield House Inn, 200 Warfield Rd., Charlemont, 888-339-8439, warfieldhouseinn.com.

6. Block Island, Rhode Island

One hour, 45 minutes by car to ferry

Natural Selection | Afternoon sun glistening on the clay bluffs, seagrass waving on a stretch of reclaimed farmland—nearly half of Block Island is designated as conservation land, and the other half is so picturesque that it might as well be. With 10 compact square miles of land area, you can bike anywhere in under 20 minutes, so it’s easy to spend all weekend on two wheels.

Stay: Hygeia House, 582 Beach Avenue, Block Island, Rhode Island, 401-856-9920, thehygeiahouse.com. See Block Island Ferry schedule at blockislandferry.com.

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