Last Updated April 26, 2022 4/26/2022

10 Best Massachusetts Weekend Getaways

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If you’re looking for a weekend getaway in Massachusetts, or nearby, you’ll find a wealth of options to choose from. Whether you want to go to the beach, the mountains, or enjoy exciting entertainment, this region of the United States has an exciting nearby area to explore. From the famed Martha’s Vineyard and Nantucket to a picturesque mountain town in nearby New Hampshire and coastal gem in Rhode Island, here are the best Massachusetts weekend getaways.

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Martha's Vineyard
Martha's Vineyard

Martha's Vineyard

Martha’s Vineyard is a popular weekend getaway for many east coast residents, home to picturesque lighthouses, sandy beaches, and the chance to enjoy unspoiled nature at spots like the Felix Neck Wildlife Sanctuary. Oaks Bluff, located on the northeastern shore is known for its unique, vibrant-colored gingerbread cottages that give the town a storybook feel and hosts beaches that face into Vineyard Sound and usually have very minimal surf, making it ideal for swimming. You can also ride on the country’s oldest carousel, the Flying Horses Carousel, which has been spinning since 1876. Book an overnight stay in a quaint cottage rental or luxury hotel.

Nantucket
The beautiful Nantucket shore

Nantucket

Nantucket is both the name of the small island and town, located 30 miles off the coast from Cape Cod. Accessed by a scenic ferry ride, here you’ll find gorgeous beaches, grand mansions, upscale restaurants, an interesting mix of unique shops, lighthouses, peaceful harbors, a whaling museum, and multiple paths that branch off in every direction for hiking or biking. There are more than 800 pre-Civil War houses in the historic district, where you can wander the streets, gazing up at the old captain’s homes and their magnificent architecture. If a romantic weekend is what you have in mind, it also boasts countless romantic B&Bs and inns.

Provincetown
Provincetown in Cape Cod, MA

Provincetown

Situated at the far tip of Cape Cod, Provincetown is famous for its spectacular surroundings that include vast sand dunes and over 30 miles of beaches. One of the cutest beach towns in New England, it also offers an especially colorful downtown that hosts everything from grand mansions and fine eateries to amazing seafood shacks, fudge shops, art galleries, and book stores, as well as being an ideal spot for some very interesting people watching. There are numerous trails to hike or bike that wind through the Cape Cod National Seashore – offshore, watch for the humpback whales and seals that are frequently spotted, and on land, for coyote, red fox, painted turtles, raccoons, and river otters that live in the salt marshes.

Sturbridge
Old Sturbridge Village in Sturbridge, MA

Sturbridge

History truly comes alive at Old Sturbridge Village in the charming town of Sturbridge, located just an hour from Boston. Here, you’ll step back into life during the early 19th-century, and wander through over 40 historic buildings from an old schoolhouse and church to a pottery shop, homes, stores, and more. The area is surrounded by exceptional natural beauty as well, with hundreds of miles of hiking and water trails for exploring. The waterways are ideal for canoeing, kayaking, and fishing.

Bretton Woods, New Hampshire
Mount Washington National Park in Bretton Woods

Bretton Woods, New Hampshire

Bretton Woods, located in the White Mountains, is known as the home of New Hampshire’s largest ski area, but it also has plenty of activities during the warmer months of the year. One of the most popular things to do is to ride “The Cog,” the Mount Washington Cog Railway which runs both steam and biodiesel-powered locomotives that climb the 3,500 feet or so up to the highest summit in New England at 6,288 feet. From here, passengers enjoy vistas that span the valleys and mountains of New Hampshire, Maine, Vermont, Canada, and the Atlantic. The Omni Mount Washington Resort, one of the last surviving handful of New Hampshire grand hotels, makes for an ideal stay nearby and hosts two golf courses, a huge spa, horseback riding, and more.

Block Island, Rhode Island
Day at the beach on Block Island, Rhode Island

Block Island, Rhode Island

Block Island is located just 12 miles off the Rhode Island coast, a short drive from many Massachusetts cities. Take the 15-minute plane ride from Westerly or the 30-minute high-speed ferry from Point Judith and you’ll enter a whole new world, far from the chaos of the city. Here you’ll find true tranquility, with seagrass gently swaying in the wind in more than half the island that’s designated as conservation land, as well as paths for biking riding, and the opportunity to kayak or paddleboard on the water. With only 10 square miles of land, you can bike anywhere in less than 20 minutes.

Brattleboro, Vermont
Brattleboro, Vermont

Brattleboro, Vermont

Brattleboro is a pretty town on the corner of three states that is famous for its farmers’ market as well and its liberal, counter-culture thinking. It prides itself on being one-of-a-kind, and is home to an outstanding local theater, great local bands, a museum, and an art center – its visual arts scene is the oldest and most deeply entrenched in the region – as well as hosting a number of unique shops,  fabulous eateries, and inns.

Portsmouth, New Hampshire
Portsmouth, New Hampshire

Portsmouth, New Hampshire

Located between Boston and Portland, Maine, Portsmouth is a hidden foodie’s delight, with restaurants that make it worth visiting for a weekend getaway, like Jumpin’ Jays, famous for its fresh fish and Cava, an intimate tapas bar. In between fabulous eats, step back in time at the Strawberry Banke Museum, an indoor/outdoor living history museum that traces Portsmouth’s earliest history, all the way back to 1623. It includes over 30 buildings and eight gardens, showcasing a slice of life from a bygone era, along with costumed characters and traditional craft demonstrations.

Portland, Maine
lighthouse on the coast, Portland, Maine

Portland, Maine

Portland, Maine is fast becoming one of the nation’s top foodie cities, and it’s ideal for outdoor adventurers too. It’s home to a stretch of the Appalachian Trail and offers not only great hiking but biking, swimming, and just about every type of paddling you can think of. Enjoy walks along the soft sandy beaches along the coast and getting out on the water in a kayak.

Foxwoods Resort Casino - Mashantucket, Connecticut
Foxwoods Resort Casino

Foxwoods Resort Casino - Mashantucket, Connecticut

While you’d probably think Las Vegas would play host to America’s biggest casino, it’s actually Foxwoods. Foxwoods Resort Casino in Connecticut is operated by the Mashantucket Pequot Indian tribe and is easily accessible from many east coast cities, including Boston. Opened in 1968, it has a whopping 4.7 million square feet of gaming space across six casinos, with more than 7,000 gaming machines and 17 different types of table games as well as one of the world’s largest bingo halls. It also offers a two-story arcade for families with children. It also has four hotels, with various rates and room types to suit most budgets.

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