Forget Cape Cod: 7 magical New England towns to visit instead this Labor Day Weekend

Less than 90 minutes from Boston, Ogunquit is ideal for a day trip or an overnight stay at one of the town’s dreamy properties. With a year-round population of roughly 1,500, the compact Maine town is easy to explore on foot.

To be at the center of the action—steps from Ogunquit Beach, Marginal Way ocean walk, and downtown shops and restaurants—book a stay at Seacastles Resort. The property sits at the entrance to the Marginal Way and features an indoor heated pool, indoor Jacuzzi, and seasonal outdoor hot tub.

For something a little farther from downtown, stay in a cottage at the Dunes on the Waterfront. The property offers easy access to Footbridge Beach, Ogunquit Lobster Pound, and kayaking on the tidal river.

There’s a reason travelers from around the world flock to Martha’s Vineyard. For a quintessential island stay, book the stunning, husband-and-wife-owned Nobnocket Boutique Inn, a Michelin Key property in Vineyard Haven.

Originally from London and Liverpool, owners Annabelle and Simon Hunton bring a touch of English splendor to the Massachusetts island. The inn’s central location makes it easy to explore local beaches and coves, Vineyard Haven’s Main Street shops, the Martha’s Vineyard Museum, and neighboring towns including West Tisbury, Oak Bluffs, and Edgartown. It is a peaceful, adults-only inn—and an equally tranquil home base for a long weekend.

Nantucket, Martha’s Vineyard’s sister island, may be smaller, but it offers a livelier nightlife scene for anyone looking to savor the last long nights of summer.

Stay at The Brant, a cedar-shingled boutique hotel in Brant Point, just minutes from downtown and steps from the beach. From there, it’s an easy bike ride to Jetties Beach, Brant Point Lighthouse, the Juice Bar, and other Nantucket icons. If you want to skip Cape traffic, take the Commuter Rail to Hyannis or New Bedford and ferry from there. Or you can opt for a quick 30-minute flight to the island.

If you’re car-free and sticking to the MBTA map, Gloucester is the place to go. The city offers some of New England’s best beaches and is an easy, direct trip from Boston on the MBTA Commuter Rail’s Newburyport/Rockport Line.

Good Harbor Beach is home to the Inn at Good Harbor Beach, an oceanfront retreat that puts the sand practically in your backyard. Downtown Gloucester is about 30 minutes away on foot, and the seasonal Stage Fort Park Shuttle connects the Gloucester MBTA station, downtown, Good Harbor Beach, and Rocky Neck—making it easy to explore without a car.

Ogunquit’s neighboring town, Kennebunkport, is one of New England’s most charming small towns—and it’s especially spectacular in summer. Check out the surf scene at Gooch’s Beach, then head to Dock Square for açai and coffee at Fia Fia, followed by sushi at Rosella. Spend the night at the Yachtsman Hotel + Marina Club for a waterfront stay that feels straight out of Architectural Digest. For a historic family-friendly stay check out The Nonantum Resort.

If the Beach Boys adopted a New England town, York, Maine, would be among the first on the list. The town has that retro 1950s beach energy, with two main beaches: Long Sands and Short Sands.

Kicking off the long weekend on September 5 from 6 to 10 PM, the town will host an oceanfront concert and bonfire, with all proceeds benefiting a local charity and the food pantry. Stay at The Viewpoint Hotel for direct views of Maine’s Nubble Lighthouse. For a stay across from the town’s largest bonfire, book a room at The Nevada Hotel.