5 Ideas for Weekend Road Trips in New England

Although the states that make up New England loom large in American history and culture, the region is surprisingly compact, with a total land area that’s dwarfed by Missouri. But despite its size, this region is packed with variety: remote mountain peaks, bustling cities, endless beaches, and idyllic farming valleys. This is great news for travelers because New England’s most compelling locales can be explored on easy weekend road trips. These are some of my favorites:

lighthouse on the coast of Cape Cod
Brant Point Lighthouse in Cape Cod. Photo © Alwoodphoto/Dreamstime.com.

Beach Escape

Cape Cod, Massachusetts

Kick off the weekend with a day on Coast Guard Beach in Cape Cod National Seashore, where you can find classic lighthouses, coastal dunes, and some of New England’s best whale watching. When afternoon rolls around, pack a hamper and head to the nearest baseball park—the Cape Cod Baseball League is the perfect place to see future baseball stars up close (and for free).

On your second day, rent a bike for a leisurely ride down the Cape Cod Rail Trail, with a stop for a fresh-from-the-sea lunch at Cap’t Cass Rock Harbor Seafood.

New Art and Old Books

Providence, Rhode Island

The capital of Rhode Island is a treasure trove of culture, with the Rhode Island School of Design Museum at the heart of the action. Explore the enormous collection of modern and historic art over two easy-going days—taking advantage of free admission on Sundays—then break up your visit with forays into the city.

Browse the stacks at the Providence Athenaeum, a favorite haunt of H.P. Lovecraft, try a sloppy “murder burger” at the historic Haven Brothers Diner, or sample locavore cuisine at the refined Nick’s on Broadway.

a cascade of waterfalls over big rocks
Cool off at Warren Falls. Photo © Jen Rose Smith.

Swimming Holes and River Floats

Mad River Valley, Vermont

Hidden between two mountain ridges, the Mad River Valley is Vermont at its most picturesque, with rivers that meander past red barns and historic villages. Wait until New England is sweltering, then spend a weekend cooling off in the river.

Start with a long, slow float down the Mad River with an inner tube from Clearwater Sports in Waitsfield, bouncing over little rapids and ripples on your way from the Great Eddy Covered Bridge to one of many downstream take-outs. You can drop a car for the trip upriver, but most locals just hitch a ride back to their departure point.

Visit one of the valley’s many farm-to-table restaurants for dinner, then make a morning pilgrimage to Warren Falls, among Vermont’s most beloved swimming holes, featuring a series of green pools and jumping spots.

Music in the Mountains

The Berkshires, Massachusetts

A base in Norman Rockwell’s beloved Stockbridge is ideal for exploring the Berkshire’s thriving music scene—and musical history. The first stop is The Guthrie Center, a church-turned-musical haven founded by Arlo Guthrie, where visitors can join the energetic Saturday Hootenanny, an old fashioned jam session that’s open to all.

On your second day in the Berkshires, make your way to Tanglewood, where the Boston Symphony Orchestra spends each summer playing to a lawn full of picnickers. The open-air concert venue is famous for raising the picnic to a fine art—stop by the Elm Street Market and the Stockbridge Wine Cellar for supplies.

train chugging through fall color in New Hampshire
Enjoy the view from the Mount Washington Cog Railway. Photo © sakakawea7/iStock.

Appalachian Adventure

White Mountains, New Hampshire

The White Mountains are New England at its most rugged, and a network of Appalachian Mountain Club huts mean hikers can spend the night up high (with no camping gear required).

Save your legs by hopping the Mount Washington Cog Railway to the summit, then visit the Mount Washington Observatory to learn about the Whites’ wild weather. It’s all downhill to Lakes of the Clouds, a spectacular mountain hut with hot meals and perfect sunset views. In the morning, you can hike to the base, or ride “The Cog” back down the mountain.

Ready for a Longer Vacation?

Link these weekends up for one perfect New England road trip. Start by getting your feet wet on Cape Cod’s Coast Guard Beach, then head to Providence for some art and culture. The next stop is in the heart of the Berkshires, where you can soak up the tunes before soaking in Vermont’s best swimming holes. By the time you get to New Hampshire you’ll be ready for a hike, with sunset on the flanks of Mount Washington as a grand finale for the 10-day adventure.

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