As the leaves turn into vivid shades of yellow, orange and red, there’s no better time for a New England road trip. We traveled from Connecticut up to Maine, discovering breakpoints for memorable outdoor dining, ridge views of bright deciduous trees, quaint shops and boutiques and picturesque hotels for respite in along the way.
Whether you follow our four-state itinerary or break it down for a smaller-scale trip, these destinations deliver endless charm and bountiful foliage. Hop in the car and start exploring New England during its prime season.
Point yourself toward Washington, which sits in the heart of Litchfield County is and just a two-hour drive from New York City. There, the recently renovated Mayflower Inn and Spa, Auberge Resorts Collection immerses you in nature. The inn is tucked inside nearly 60 acres of woods and landscaped gardens reminiscent of an English countryside retreat.
Stroll through the Shakespeare Garden and American Poets Maze, which pays homage to U.S. poets by inscribing their words on plaques that are scattered throughout. Maybe a paddle around the lake with a canoe picnic lunch is more your style. You also can choose active pursuits, like archery with an instructor, cooking and mixology classes or pedaling the hills with a borrowed hotel bicycle. Or Zen out with a private meditative session in the yoga space or nearby forests, or a treatment in the light-filled spa.
While you’ll be tempted to unwind in the Mayflower Suite’s warm, elegant living room with dark wood and leather accents, head to the enclosed porch, where you can settle into a rocking wicker chair with a cocktail and take in the cool evening air. When you need to warm up, return inside and nestle into a plush sofa in front of the fireplace or slip into the feather-topped bed.
When it’s time to hit the road, Litchfield County has plenty to see. Hike up Steep Rock Preserve for outstanding vistas of the Clamshell section of the Shepaug River Valley and roam through a 235-foot hand-built curved tunnel in Steep Rock Ridge. Afterward, refuel at Community Table, a Litchfield Hills fixture that serves local, seasonal food (like seared Atlantic halibut with squash chowder, Litchfield bourbon and chive oil) in a lively and chic setting. Visit the larder and buy a couple of bottles of the house vinaigrette for your at-home salads. On your way out, swing by the town of Washington Depot and run into Five Janes to pick up playful earrings or an animal-patterned swaddling blanket.
Cruise down Interstate 95 and it won’t be long before you have to pull off the road and meander down to The Vanderbilt, Auberge Resorts Collection. Built in 1909 by scion Alfred Gwynne Vanderbilt and restored to celebrate the Gilded Age glamour of the era, the red-brick mansion is well positioned so that you can take in Narragansett Bay and all of the art, entertainment, shopping and dining pleasures of Newport.
Upon check-in, you may be directed to sit near the wood-burning fireplace in the lobby, where you can peruse many books on art and culture, or maybe the timing will be right for a sunset cocktail on The Vanderbilt’s rooftop bar. Or wait until your Admiral One Bedroom Suite is ready and sip a sundowner from the sitting area — some of these uniquely decorated accommodations also have partial water vistas.
When you crave fresh air, ask the concierge to arrange a seal-watching excursion or a Newport mansion tour, including a peek inside the renowned Breakers, one of the grandest among the area’s Gilded Age summer homes. For a meal outside of the hotel, Locanda is a nearby favorite for handmade pasta, and it offers indoor and outdoor dining. Get the shaved Brussels sprouts salad with pistachios and pecorino, and the whipped ricotta ravioli with eggplant and torn basil — it’s the ultimate comfort food. Before making your way back to The Vanderbilt, grab a cone at Frosty Freez, Aquidneck’s go-to soft-serve spot.
After relaxing coastal time in Rhode Island, head to the city for a night or two. The architecture and design of Four Seasons’ new Boston skyscraper, One Dalton Street, are impressive, but we stayed in the original for a dose of nature in the city. Four Seasons Hotel Boston puts you steps away from the Public Garden and the Boston Common.
Request a Garden View Executive Suite for a bit more space and prime vistas. The modern, updated accommodation comes in soothing blues, grays and golds, and the oversized bay windows afford a bird’s-eye look into the trees and green spaces.
Regardless of temperature or season, make sure you pack your suit because you will want to swim in the eighth-floor indoor pool and whirlpool overlooking the Public Garden and Beacon Hill.
Dry off and pop over to nearby Eataly to scoop up pasta, sauces, olive oil and other artisanal Italian ingredients, then retreat to the new patio for a mulled cider spiked with Flor de Caña rum and Averna Amaro among hay bales and pumpkins.
In the morning, visit Flour Bakery and Cafe for a quick meal that you can bring into the Public Garden. We love the breakfast egg sandwich with arugula, fresh tomato and dijonnaise, but get an order of the housemade Oreos, too.
After a taste of city life, begin your drive north toward Salem for some history, witch lore and cobblestone street strolling. If time permits, check out the Peabody Essex Museum, where you can tour Yin Yu Tang, a reassembled 16-bedroom family home dating back to the Qing Dynasty. Also peek at Anila Quayyam Agha’s “All the Flowers Are for Me,” a brilliant sculptural chamber of light and shadow that prompts reflection on all the common threads that are woven into our lives.
On the other side of Salem, turn off from the main thoroughfare to find a less-beaten path through Marblehead. Uncover hidden public walkways that residents made 300 years ago from their homes to the sea, which was the source of their livelihood, and learn about the locals with a walk through Revolutionary War-era cemeteries.
A stop at The Muffin Shop is a must for Joe Froggers, molasses-rum cookies that will keep you energized for hours. Then duck into The Spotted Hound, a beloved lifestyle boutique selling new and vintage goods. Ask for help from the owners and they may direct you toward a polished copper saucier for making a nutmeg-laden bechamel, locally made candles scented with seasonal notes or a soft, lambswool tartan blanket to throw over your knees when resting on a bench outside to take in the sea air.
Continue onto Beverly, where you can grab some baked treats at Frank market, where owner/operator Frank McClelland (formerly chef of Boston’s famed L’Espalier) makes local ingredients the star of the show. Next, hop on Route 127 and go to Beverly Farms through Manchester-by-the-Sea and veer off to the town of Essex for a meal along the salt marshes at CK Pearl, where the service is fluid, the menu is diverse and the river traffic will keep you entertained and wishing you could jump aboard. Warm up with the “chowda,” which arrives with a few fried clams and crispy pork belly on top and brimming with sea flavor. And don’t bypass the elevated cocktails, like the Dotty O’Shea, made of Jameson, coffee and whipped cream, or the Corpse Reviver No. 2 with gin, Lillet Blanc, triple sec, lemon and anise. Cap it off by window shopping at Essex’s unique antique and specialty boutiques.
Kennebunk and Kennebunkport, Maine
For the final stretch, venture to the bucolic White Barn Inn, Auberge Resorts Collection in Kennebunk. Check into the 27-room property recently renovated by Jenny Wolf Interiors, put on your sneakers and prepare for a customized apple orchard excursion, arranged by the concierge team. Or opt for a class in chocolate making or wine-and-cheese pairing.
Afterward, treasure the time in one of five stand-alone cottages with coastal touches and a homey ambiance. Our favorite is the secluded Friendship Cottage with a stone hearth and wood-burning fireplace. Take a glass of wine out onto your riverfront patio, where you can linger and listen to the sounds of nature.
Freshen up for dinner with a soak in the large, infinity-edged tub — though you won’t want to get out. But dinner calls and you can’t miss a chance to dine at the brand-new Little Barn. On the balcony among the leafy trees, savor warm goat Brie with rhubarb jam and pickled blueberries or the herb-roasted chicken with mustard greens. If you are lucky, the daily specials will include the truffled caviar lobster roll, a perfect combination of truffled earthiness and brine from the sea.
The next morning, you’ll find a complimentary basket of steaming coffee and housemade pastries waiting at your door. Finish your breakfast and then bike to town. Explore galleries specializing in locally made crafts and art as well as boutiques like Minka, which sells sustainably made hand balm and body butters that will help combat winter dryness.
For a real biking adventure, pick up an order of fried seafood at The Clam Shack, a staple since 1968, and bring it along for a picnic on the bridge over the Kennebunk River or at nearby Rachel Carson National Wildlife Refuge, which has views of the salt marshes and estuaries. Add a pit stop at Snug Harbor Farm, a remarkable place where you can chat with farm animals, wander through the gardens and learn about agronomy from founder Tony Elliott or his expert staff.
Then return to the inn for the grand finale: a Five-Star dinner at the stunning The White Barn Inn Restaurant. Order the chef’s lobster menu for a six-course Maine culinary experience and you will not be disappointed. The rack of lamb, accompanied by a fresh lobster bordelaise, will be a delicious lasting memory of your New England road trip.
