Massachusetts is home to several of the country’s most historic cities and towns such as Salem and Boston. In addition, it boasts oceanfront communities, charming New England culture, and a trendy art scene. Head inland to central Massachusetts for country fair fun, as well as plenty of breathtaking natural areas perfect for exploring and hiking. There are numerous Massachusetts vacation rentals to choose from for your Labor Day weekend getaway. Check out the top cities and towns in this New England state.
Sturbridge is a small town known mostly for Old Sturbridge Village, a living history museum with 40 historical buildings that illuminate life during the 1830s. The village has everything from a church to a water-powered mill. Stop in at the blacksmith shop and see a smithy in action, or watch pottery being created. Every Labor Day weekend the village hosts special events from Family Fun Days to Militia Weekend where families get to play old-school games, enjoy puppet shows, and do other kid-friendly activities. Best of all, the employees wear period costumes so you feel as if you’ve time traveled. Afterwards, explore the 1,400-acre Wells State Park, which features kayaking and swimming on the Walker Pond. There’s also hiking and biking on a dozen miles of trails.
Barnstable lies on the peninsula between Cape Cod and the Atlantic, a great place to grab a vacation rental if you want to have fun in both bodies of water. The city’s Town of Barnstable Public Lands boasts a beach and Cape Cod access, ideal for laying out in the last sun rays of summer. You can also explore the Great Marshes via canoe or kayak. Lou Lou’s Leasing and Cape Cod Bay Charters offer watercraft rentals. End your summer with the annual Labor Day Road Race 5k, and then stop off at the Truro Agricultural Fair. The fair is all about Cape Cod with locally grown foods and live entertainment.
Boston is the city to visit during Labor Day weekend if you want plenty of options. The city goes all out on the holiday, saluting the end of summer with fireworks over the harbor, which you can enjoy close up on a Boston Harbor Cruise. Head to Fenway Park for a concert, or head up north to Newburyport where you can indulge in an entire musical weekend at the Riverfront Music Festival. If you have children about, go to Lawn on D, a park in the heart of downtown area boasting games, street performers, live entertainment, movies at night, and other family-friendly fun all weekend long.
4. Martha’s Vineyard
Martha’s Vineyard rocks the Jazz and Blues Summerfest over Labor Day weekend, a festival that includes dozens of performers, food vendors, and artisan markets. Afterwards, spend the waning summer days relaxing on Lucy Vincent or South beaches. Try a more active approach to wishing summer a fond farewell by kayaking and boating around the island and Long Point Wildlife Refuge Beach. Rent some water gear at Wind’s Up or Island Water Sports.
If you’re on Nantucket, another island off the coast of Massachusetts, then you can join others onboard the Nantucket Lightship, a historic vessel that also gives passengers a front-row view of the island’s Labor Day fireworks display. Bring some takeout from Old South Diner or Oath Pizza to the fireworks, and enjoy the show. While in town, visit the Whaling Museum and Brant Point Lighthouse, and play a game of golf at the Sankaty Head Golf Club. The ocean views add a relaxing feel to your golf game. Plus, you can catch the Sconset Bluff Walk, which starts right across the road from the golf course.
Salem lies where the Crane River and South River meet the Atlantic Ocean, meaning that a tour of the area via Mahi Cruises is a must. Continue to familiarize yourself with the area and its unique history with Black Cat Tours. Aptly named, this guide service takes you on foot to the dark moments and places of Salem’s Witch Trials. Make sure to stop at the House of the Seven Gables. Grab a few sandwiches from Milk and Honey and enjoy the weather at Waikiki Beach.
Located in central Massachusetts, Spencer hosts an annual country fair that’s all about the rural life. Watch a tractor pull (and then tour antique tractors), root in a log sawing contest, and enjoy a demolition derby. Kids are sure to love schmoozing with Juno the Hero Dog while watching acrobats. Naturally, there are a large variety of delicious food vendors featuring your favorite fried foods. Spend some part of your weekend exploring the Massachusetts Audobon Burncoat Pond Wildlife Sanctuary and Sibley Farm. There are plenty of hiking trails through the 360-acre farm that pass through woods, over meadows, and by ponds and rivers. Head down to Spencer State Forest for some swimming in Howe Pond and kayaking down Cranberry River.
Labor Day in Somerville means Starlabfest located at ARTfarm. This festival is a flea market meets a fair. You get live music, food vendors, and local artisans in conjunction with games and raffles. Get into history with The Freedom Trail; it leads to the Bunker Hill Monument. With the city’s proximity to Boston, you can also cross the Charles River via the Freedom Trail and tour the rest of the historical sites.
Located on the northeastern-most tip of Massachusetts, Gloucester boasts cooling winds, seaside views, and a quaint New England experience. Labor Day is when the annual Gloucester Schooner Festival takes place which celebrates the area’s maritime history. The three-day event starts off with a parade, ends with fireworks, and is filled with boats and food, including lobster bakes and all your favorite seafood. Watch the schooners in the Parade of Sail and cheer on the winner in the Mayor’s Boat Race. Even kids can get into the action and ride on the vessels. In the middle of this festival is another: Maritime Heritage Day. Learn about the area’s boating history, enjoy live music, tour a schooner, and tour Maritime Gloucester Museum’s exhibits.
Northampton, which also lies in central Massachusetts, celebrates Labor Day weekend with the Three County Fair, a massive event that draws in thousands of people over four days. Not only are there the usual amusement rides, fried fair food, and tons of animals, but this event throws in pig racing, high-flying frisbee dogs, and a horse show as well. Set aside a few hours to explore the Fitzgerald Lake Conservation Area where you can hike and kayak; the Bikeway is a favorite trail among locals.
Ready to go? Check out these amazing Massachusetts vacation rentals on Tripping.com.