On the Road Again

The ultimate guide to your New England summer road trip.

Written by Stacey Marcus

There’s never been a better time to pack up the station wagon, hit the road less traveled and explore your backyard. “Shake off the quarantine and homeschooling and rediscover your own New England,” says Chris Jennings, the executive director of Discover New England. “From beach walks and rooms with seaside views to mountains and outdoor adventures, our region can make you feel safe, relaxed and welcome.” With that in mind, we cherry-picked six special spots for you to create a gallery of sweet summertime memories with your squad.

Rhode Island

A summer stay in South Country promises unforgettable memories and plenty of Instagrammable moments. The area is chock-full of summer fun, with twenty public beaches, whale watching cruises, lighthouses and historical sites. Watch Hill is an ideal destination to set up base. Stay at Ocean House, one of only thirteen properties in the world to earn Forbes’ five-star award in three categories (hotel, restaurant, spa). Set high on the bluffs, the resort offers an array of family friendly activities including culinary classes, movies in the screening room and croquet. The property boasts stunning guest rooms, signature suites and cottages with full kitchens and laundries.

Take a stroll downtown and on the way stop at Ella’s Fine Food & Drink, an upscale dining destination run by James Beard nominee Jeanie Roland, and where Taylor Swift and Lorde once took a cooking class. Enjoy a ride on the Flying Horse Carousel, the nation’s oldest continuing operating whirligig. Be sure to go stargazing at Frosty Drew Observatory in Charlestown covered by the darkest stretch of night sky between Boston and New York City. The Fantastic Umbrella Factory is brimming with gardens, a bamboo forest, shops with gems from area artisans and even a petting zoo. Pick flowers and berries from local farms like Clark Farms in Matunuck and Farmer’s Daughter in Wakefield. Take a day trip to Narragansett and enjoy dinner (capped with mudslides) at the Coast Guard House. Travel to Westerly to enjoy a bite at the Cooked Goose and grab a coffee or glass of wine at the Savoy Bookshop and Café.


Looking to meander in meadows, fish in lakes or ride on a wooden roller coaster? Take a trip to southwestern Connecticut and stay in Washington, a spot so charming that it served as inspiration for Gilmore Girls’ fictional town of Stars Hollow. Washington is also the home of the freshly reimagined Mayflower Inn & Spa, Auberge Resorts Collection. Its three thousand acres of woodlands offer families a lavish country escape to enjoy fly-fishing, archery, tennis and croquet along with a heavenly spa experience.

Be sure to visit White Memorial Conservation Center in Litchfield and explore the four-thousand-acre nature center and wildlife sanctuary where you can hike, horseback ride, camp and birdwatch. A trip to nearby Hidden Valley Preserve unveils seven hundred acres of meadows and forests and seventeen miles of trails while a visit to the Institute for American Indian Studies gives families an opportunity to time travel back ten thousand years and discover Native American history.

Pop by G.W. Tavern, an 1850s colonial home with river views that gives a nod to our first president, for some American favorites or enjoy a tasty brick-oven pizza at The Owl in Preston. Lake Waramaug State Park in Kent is the perfect place to pack a picnic lunch and spend the day swimming, enjoying cartop boating and fishing. Enjoy some old-fashioned amusement park joy in Quassy Amusement Park in Middlebury where you can ride on a wooden roller coaster. Cap off a summer day with a farm fresh ice cream cone at Arethusa Farm Dairy in Bantum.


Sparkling along the coast of Cape Cod, Brewster is a picturesque destination for your family to experience the balm of a beach break. This summer, Ocean Edge Resort & Golf Club brings back a lineup of private experiences for families to enjoy, including private oyster bed tours in the Brewster flats, individual archery lessons, private beach fires during sunset, individual picnic baskets and private and beach yoga.

Nearby activities include bike riding on the twenty-five-and-a-half-mile Cape Cod Rail Trail, a trip to the Cape Cod Museum of Natural History and sun-filled days at the forty-mile stretch of Cape Cod Natural Seashore that includes six beaches, eleven hiking trails and five cycling trails. Whale watching is a must-see when on the Cape as are the Art’s Dune Tours in Provincetown where you can see one-hundred-foot sand dunes, wildlife, indigenous flora and nineteen dune shacks.

Stand in line at Cobie’s for a lobster roll, enjoy seafood classics in a charming cottage at the Brewster Fish House or stop by Café Alfresco for light bites. Take a trip to the Corner Store for a breakfast burrito or Laura and Tony’s Kitchen in Eastham to savor great slow food made from scratch. When it comes to shopping, gems can be discovered at Sydenstricker Glass and the Handcraft House. Goose Hummock Shop is the go-to place for all things hunting, fishing and marine and water sports. Last but not least, be sure to put Taylor-Bray Farm in Yarmouth Port and Chatham Fish Pier on your must-do list.


Summer in Vermont is one of New England’s best-kept secrets. Stowe is an ideal spot boasting fewer crowds, fresh mountain air and an array of spaces to explore outdoor activities. A luxury resort and spa designed around open spaces, Topnotch Resort is tucked into 120 acres of woodland at the base of Vermont’s highest peak, Mount Mansfield. The resort offers outdoor activities including hiking, fishing, mountain biking or playing tennis on one of six outdoor tennis courts.

Ribbons of mountain roads remind visitors of the green scene’s healing power. Take a drive up the Auto Road and see the view from the top of Mount Mansfield. Enjoy a bike ride at Trapp Family Lodge and end at the property’s Kaffeehaus. Another great bike ride is the flat five-mile paved path on the Stowe Recreation Path, where you can see quintessential New England scenes and pass by local shops and eateries along the way. A stop at Creemee Silo at Tres Amigos restaurant is a treat for the kids while parents can enjoy cider to go from Stowe Cider.

Enjoy hibachi and outdoor patio dining at Sushi Yoshi. Further up Mountain Road is a cluster of shops and restaurants, including those at the Red Barn Shops, where you will discover Yellow Turtle, an adorable children’s store. Sundays are the best day to visit the area, as the Stowe Farmers Market is in the field next to the Red Barn Shops. Don’t leave Stowe before you take a dip in a swimming hole or enjoy a family hike at Moss Glen Falls or Stowe Pinnacle.


In 1884 people seeking a quiet coastal respite would visit The Claremont on Mount Desert Island for a classic summer retreat. Fast-forward over 135 years and this New England grande dame reopened this May after an extensive renovation. The reimagined hotel boasts gorgeous accommodations and bespoke experiences including boat cruises, fishing, cruiser bikes, golf cart rentals and nature hikes.

While in the area, explore the butterfly garden at Charlotte Rhoades Park or meet artist-in-residence Steven Valleau at Wendell Gilley Museum and learn about the master plumber-turned-master-carver’s more than ten thousand sculptures of wild birds. Bite into an authentic Maine lobster roll (or lobster tacos or lobster grilled cheese) on the rustic pier at Beal’s Lobster or take a sailing lesson at Mansell Boat Rentals. Keep the lobster theme going and take a lobster cruise with Acadia Lobster Cruise on a vintage 1966 wooden boat.

Families who enjoy hiking should check out the Beech Mountain Loop and Beech Mountain Valley Trail. Climbable within two hours of the Beech Hill Road parking lot, Beech Mountain Loop is a less-crowded alternative to Cadillac Mountain. If you’re seeking a slightly longer hike, choose the Beech Mountain Valley Trail. Go mountain biking or book a sea kayaking tour on the quiet side of Acadia National Park, one of the East Coast’s most popular destinations, or take a ferry to the Cranberry Isles.

New Hampshire

New Hampshire’s White Mountains offer the perfect escape where you will discover fewer people and more mountain air. When the Mount Washington Hotel opened in 1902, vacationers would visit to escape maladies like yellow fever and cholera. Now the Omni Mount Washington Resort, the hotel provides an array of accommodations ranging from boutique rooms to luxury suites spanning three thousand square feet, and recently added sixty-nine new rooms in its Presidential Wing. With eighteen dining venues, a new gondola to view the majestic scenery and a plethora of outdoor activities like golf, mountain biking, carriage rides and hiking, you need not leave the property but there is plenty to explore in the area.

On the western slope of Crawford Notch is Arethusa Falls, the highest waterfall in New Hampshire. Natural wonders including waterfalls and sweeping vistas abound in Flume Gorge in Franconia Notch State Park. If your family fancies antiquing, they will adore the quaint towns of Sugar Hill, Bethlehem and Littleton.

Enjoy bountiful breakfasts at gems like Munroe’s Family Restaurant in Twin Mountain or Grandma’s Kitchen in Whitefield. Bethlehem is a nice day trip where you can kayak or pop by WREN (Women’s Rural Entrepreneurial Network) to enjoy the works of more than three hundred local artisans. Rek-lis Brewing Company is a fun stop for lunch or dine at Rosa Flamingo’s for dinner. You’ll love returning to the Mount Washington Resort to hang out on the back deck and delight in the spectacular views.

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