Looking for a great Memorial Day weekend escape? Massachusetts offers lots of fabulous options, from charming beach towns and tranquil inland countryside to city delights. No matter what your idea of an unforgettable escape, you’re sure to find your perfect getaway among these destinations.
Martha's Vineyard
There are many reasons to visit Martha’s Vineyard over the long weekend. On Saturday and Sunday at the Historic Grange Hall in West Tisbury, the annual Artisans Festival will take place, which offers the opportunity to view works by island artists, watch demonstrations and enjoy lots of great food. In Oak Bluffs on the north shore, you’ll find beaches facing Vineyard Sound, typically with minimal surf, making it ideal for swimming or wading. The Flying Horses Carousel will be open, too, offering the chance to take a historic ride on the oldest carousel in the country, a national landmark that has been spinning since 1876.
Provincetown
Located at the far tip of Cape Cod, Provincetown is one of the cutest beach towns in New England. It’s the perfect excuse for a vacation and the opportunity to wander through the colorful downtown area, with its wide range of eateries from fine dining to seafood shacks, fudge shops, art galleries, and bookstores. You can also take advantage of the more than 30 miles of beautiful beaches here too, with the water warming just in time to make it ideal for a refreshing dip.
Falmouth
Falmouth is one of the most charming small towns in Massachusetts, located at the southwestern tip of Cape Cod. It is another great place to kick off summer over the holiday weekend, especially for families. Everyone will be flocking to the beach, though there are lots of other things to do as well. You might rent bikes and pedal along the Shining Sea Bikeway, which starts in Falmouth and travels 10 miles along the canals and the coast. On the holiday itself, watch the annual parade, with the procession beginning at Falmouth Village Green.
Plymouth
Plymouth offers the chance to take a walk back through time, visiting the first Pilgrim settlement, which dates back to 1620. Best known as the site of the landing of the Pilgrims who were fleeing religious persecution in Britain, it was here that the Mayflower landed, and colonization in the area began. Hop aboard the Mayflower, a full-scale replica of the ship, complete with exhibits and tours led by costumed docents. At Plimoth Plantation, a living history museum, you can see Plymouth just as it was in its early years.
Sturbridge
Sturbridge is one of the oldest towns in Massachusetts, settled back in 1729. It looks like a Norman Rockwell painting comes to life and hosts the Old Sturbridge Village, the largest outdoor living history museum in the Northeast. Here you can step into the shoes of those who lived here in the 1830s, complete with costumed guides. Over Memorial Day Weekend, you can learn how New Englanders reared sheep for their wool at the annual sheep shearing festival, Wool Days, which includes farmers performing sheep shearing, while experts show off the sheep herding skills of border collies. In town, there are all sorts of fun boutiques and antique shops to explore, and nearby at Wells State Park, you can enjoy canoeing and swimming in a tranquil pond.
Boston
Boston offers a ton of attractions for just about every type of visitor. The Boston Calling Music Festival is a great place for music lovers, but if you’re a history buff, walk the two-and-a-half-mile Freedom Trail that begins at Boston Commons, passing the Granary Burying Grounds, where you’ll find the graves of Sam Adams, Paul Revere, John Hancock, and Ben Franklin’s parents. The Boston Massacre Site and Paul Revere’s House are also along the way. Brew lovers won’t want to miss a tour of Sam Adam’s Brewery, and art enthusiasts can explore the Institute of Contemporary Art, filled with contemporary artists’ explorations of the physical and unseen world.
Salem
Salem is an especially popular Halloween destination, but it offers lots to experience year-round, including Memorial Day Weekend. It’s home to the Peabody Essex Museum, which opened its doors back in 1799 when museums were officially known as a “cabinet of natural and artificial curiosities.” It holds 1.8 million pieces of maritime, Asian, African, Indian, and Oceanic art, plus 22 historic buildings, including the Qing Dynasty Yin Yu Tang house. The city also has strong literary connections as the birthplace and home of Nathaniel Hawthorne, which is open for tours, and it’s also the infamous site of the Salem Witch Trials, which can be experienced through re-creations.
Nantucket
Nantucket is both a small island and a town, accessed via a scenic ferry ride from the coast of Cape Cod. Over Memorial Day Weekend, you can watch the Figawi Regatta, a special event that brings some powerboats and sailing vessels to race from the Hyannis Port Jetty and crosses the finish line at the Nantucket Jetty. A number of other races and regattas will be through the weekend, along with live entertainment and parties. You can also enjoy the island’s many fine restaurants, an intriguing mix of shops, peaceful harbors, picturesque beaches and lighthouses, a whaling museum and bicycle paths that branch off in every direction, leading to various but all gorgeous picture-perfect stretches of sand.
