Where To Spend Labor Day Weekend In New England

Photo Credit: Ocean HouseLabor Day marks the final flourish of summer, a long weekend tailor-made for indulgent escapes. Across New England, luxury resorts and inns are celebrating the season’s last hurrah with champagne clambakes, farm-to-sea dinners, sunset yoga sessions, restorative spa rituals, and more. Here’s where to savor the best of late summer in fine dining, wellness experiences, and waterside adventures.

Ocean House – Watch Hill, RI

This Forbes Five-Star icon in Watch Hill celebrates Labor Day with its signature Lobster Boil & BBQ on the Beach, a grand New England buffet held on a private white-sand shore. Guests kick back by the surf at sunset, enjoying heaping raw bar towers, grilled classics, fresh Rhode Island lobster and summer sides, all to the soundtrack of live music under the dusky sky. Culinary enthusiasts can dive even deeper at the resort’s Center for Wine & Culinary Arts, where daily wine tastings and cooking classes invite hands-on gourmand fun. And for those with a sweet tooth, evenings bring a whimsical twist: the hotel’s Below Deck After Dark dessert lounge serves up boozy milkshakes, espresso martinis and decadent treats alongside house-made ice cream – a playful late-night indulgence under the stars. Wellness seekers find sanctuary at the Ocean & Harvest Spa, the only Five-Star spa in Rhode Island, where ocean-inspired body rituals (seaweed wraps, marine mud masks), yoga on the beach, and hydrotherapy in a saltwater pool replenish body and soul. From its waterfront croquet lawn to the secret champagne garden, Ocean House exudes Gilded Age glamour and modern coastal comfort in equal measure.

1 Bluff Avenue, Watch Hill, RI 02891

Photo Credit: The Wauwinet

The Wauwinet – Nantucket, MA

Tucked between Nantucket Bay and the Atlantic, this adults-only Relais & Châteaux retreat is pure tranquility at the far edge of the island. Its acclaimed restaurant, TOPPER’S, embodies farm-to-sea luxury: try oysters on the half-shell harvested just 300 yards offshore, paired with a selection from the restaurant’s 2,200-label wine cellar, one of New England’s most celebrated. Come sunset, guests can cruise aboard the vintage Wauwinet Lady boat for cocktails on the water as the sky turns pink, then return to shore for a stroll on the inn’s private stretch of beach. Days here invite gentle outdoor pleasures where you can grab a complimentary kayak for a paddle along calm bay coves or a bike for exploring Nantucket’s winding lanes. With only 32 rooms and cottages, The Wauwinet feels like a secret, surrounded by lapping waves and wildflowers – an elegant hideaway where every element reflects Nantucket’s coastal splendor.

120 Wauwinet Road, Nantucket, MA 02584

Photo Credit: Chatham Bars Inn

Chatham Bars Inn – Cape Cod, MA

Cape Cod’s iconic seaside resort makes for an unforgettable Labor Day escape. The signature experience is the private oceanfront clambake—lobsters steamed over seaweed in a beachside pit, revealed by a chef at sunset, and served family-style at candlelit tables in the sand. By day, unwind in Japanese-inspired Zen garden cabanas with alfresco treatments like the Aroma Journey or Blissful CBD Massage, the Epicutis Body Treatment with cooling botanicals, or the SkinCeuticals Cabana Facial to restore a summer glow.

Photo Credit: Chatham Bars Inn

Evenings shine at STARS, where sweeping Atlantic views and a Norman Rockwell painting set the stage for refined coastal dining. The menu ranges from American Wagyu with truffle and Sauce Diane to Atlantic Halibut with lobster dumplings, Herb-Crusted Lamb Rack, and Szechuan Tofu with sesame crunch. Guests can also opt for the chef’s multi-course tasting menu, paired with selections from the restaurant’s award-winning wine list, recognized by Wine Spectator in 2024. For adventure, the inn’s fleet of boats offers whale and seal-watching cruises, harbor sails, and fishing trips to Nantucket or Martha’s Vineyard. Equal parts luxury, tradition, and seaside charm, Chatham Bars Inn captures the essence of Cape Cod at summer’s end.

297 Shore Road, Chatham, MA 02633

Photo Credit: Harbor View Hotel

Harbor View Hotel – Martha’s Vineyard, MA

Martha’s Vineyard’s grand dame sits at the entrance of Edgartown Harbor, overlooking the iconic lighthouse and sweeping Atlantic views. At this historic retreat (fresh off a top-to-bottom renovation), guests can sip rosé on the wraparound veranda as sailboats drift by, or head poolside to the chic Roxy Pool Bar for live music and lobster rolls/tacos served with laid-back island flair. By day, the hotel curates activities balancing wellness and exploration: start with sunrise yoga on the lawn facing the harbor. Private sessions can be arranged for a more personalized flow amid the sea breeze. Grab the keys to a complimentary Mercedes-Benz convertible and cruise the Vineyard’s scenic byways, from up-island farmland to hidden beaches, in luxurious style. Within minutes of the hotel, you can browse Edgartown’s farmers’ markets or join local guides on oyster farm tours to sample briny bivalves straight from the sea. Back at Harbor View, indulgence awaits at the brand-new Bettini restaurant serving coastal New England flavors. 

131 North Water Street, Edgartown, MA 02539

The Chanler at Cliff Walk – Newport, RI

Perched on Newport’s dramatic Cliff Walk above the Atlantic, The Chanler combines cliffside drama with Gilded Age romance. Each of its 20 uniquely styled rooms feels like a private mansion oasis, many with their own outdoor terraces perfect for watching waves crash on the rocks below. At the hotel’s Forbes five-star restaurant, Cara, dining is an immersive affair: Chef Jacob Jasinski crafts multi-course blind tasting menus spotlighting Rhode Island’s seasonal bounty, often using vegetables from The Chanler’s garden and seafood plucked from local waters. By day, the lush oceanfront lawn transforms into an Italian-inspired wine garden in summer, where a pop-up Ca’ del Bosco Franciacorta bar invites guests to linger under umbrellas with a glass of sparkling in hand. Couples can indulge in intimate, bespoke amenities, including an in-room aromatherapy bath drawn with essential oils for two and a curated Private Newport Expedition, including luxury transportation and a one-hour self-guided mansion tour. As evening falls, take a stroll along the Cliff Walk right from the property’s gates, then return to your private terrace for a nightcap by the fire.

117 Memorial Boulevard, Newport, RI 02840

Castle Hill Inn – Newport, RI

On a secluded 40-acre peninsula at Newport’s western tip, Castle Hill Inn embodies barefoot elegance and timeless New England charm. Labor Day weekend here is marked by classic coastal traditions: the inn’s resident chefs host lavish lobster clambakes on the beach, a weekly centerpiece each summer where lobsters, clams, corn and potatoes roast in a seaweed-lined fire pit by the shore. Come evening, guests gather on The Lawn, cocktail in hand, to sink into Adirondack chairs and toast the sunset over Narragansett Bay, watching as yachts glide past and the sky turns to gold. By day, you might join a guided nature walk through the wooded trails, or find your zen with morning yoga on the private beach as waves lap gently at the sand. Bonfire nights invite hotel guests to a private cove for s’mores and stargazing with an astronomer. When relaxation calls, slip into the Inn’s boutique spa, where organic lavender-oil wraps and herbal facials using flowers and herbs grown on local nearby farms to restore you with botanical bliss.

590 Ocean Drive, Newport, RI 02840

White Barn Inn, Auberge Resorts Collection – Kennebunk, ME
Labor Day brings special celebrations at this Kennebunk hideaway: guests can partake in a traditional Maine lobster boil BBQ on the lawn, cracking into butter-drenched lobster and corn on the cob in a relaxed alfresco feast. Come nightfall, step inside the property’s namesake 19th-century barn turned AAA Five-Diamond restaurant for a candlelit multi-course tasting menu staged amid weathered barn beams and white linen. Foodies can also roll up their sleeves with the inn’s interactive offerings: join the chef on Saturday mornings for epicurean cooking classes in the barn’s kitchen, or learn the art of mixology with farm-to-glass cocktail classes at the Barn Bar. Days here cater to both active and indulgent spirits. Borrow one of the Mercedes-Benz house cars to explore Maine’s scenic byways or to shuttle between Kennebunkport’s shops. Alternatively, hop on one of White Barn’s bicycles or charter a sailing excursion from the nearby marina to enjoy the ocean breeze.

Photo Credit: White Barn Inn, Auberge Resorts CollectionThe White Barn Inn Spa is an intimate sanctuary famed for its use of local ingredients. Their signature Milk and Honey Ritual features a honey-infused body scrub and soak, followed by a hot stone massage using smooth river stones straight from the Kennebunk River. Savor complimentary craft cocktails at sunset and return to house-baked treats at turndown, making White Barn Inn feel like an indulgent home away from home.

37 Beach Avenue, Kennebunk, ME 04043