As the first weekend of the summer, Memorial Day weekend is a popular time to travel and spend time with family. In Massachusetts, look forward to exploring a historic city like Boston or Salem, or enjoying a beach trip at Cape Cod. Whether you want to picnic at the Boston Common or go biking at Martha’s Vineyard, there’s something for everyone in Massachusetts. As for accommodations, book a stay at a cozy Massachusetts vacation rental to be in proximity to the most popular attractions and festivals in the New England area. Check out the nine best Memorial Day weekend getaway spots in Massachusetts.
Pay tribute to America’s fallen soldiers at the Boston Commons. This popular green space in the city becomes a field of flags when the Massachusetts Military Heroes Fund places more than 30,000 American flags on the greens. Do a little shopping on the opening weekend of the South End Open Market @ Ink Block. This market includes artistic works, food trucks, and a farmers market to pick up fresh ingredients to cook dinner back at your vacation rental. Walk the Boston Freedom Trail to see all the key sites that led to the American Revolution.
Find vacation rentals in Boston
Witches in the New World? Learn more about the infamous witch trials when you stay in Salem. The Memorial Day Parade and Ceremony start early in Salem and last until mid-afternoon. On a rainy afternoon, take a tour of the Salem Witch Museum to learn more about the trails and see sets that replicate the courtroom where the trails took place. For thrills and chills, take a short drive across the border to New Hampshire’s Canobie Lake Park, which offers some rides including roller coasters and water rides. While there, check out the botanical gardens to see the flowers in full bloom.
Find vacation rentals in Salem
Worcester is the second largest city in the state and offers an active art scene and cultural activities. Attend the Memorial Day Observance Remembrance Ceremony that includes a wreath ceremony in Hope Cemetery. This annual event is more than 100 years old. Go high at the EcoTarium. This center includes a treetop walkway and walking trails on the ground to enjoy the beautiful weather. Indoors see the stars with the planetarium show. Green Hill Park offers something for everyone with a zoo, golf course, and walking trails.
Find vacation rentals in Worcester
Find the perfect Massachusetts vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!
Soak up the sun on the beach in Falmouth. Part of the Cape Cod area, this town is a popular destination over the holiday weekend as pools open and people flock to the beach. Rent bikes from Holiday Cycles and pedal along the Shining Sea Bikeway. This rail bike path begins in Falmouth and extends for 10 miles along the coast and canals. Take a tour of the Nobska Light to learn more about the history of the area and the sea. Choose a picnic bench and get a scoop or cone from Smitty’s Homemade Ice Cream for an afternoon treat.
Find vacation rentals in Falmouth
5. Martha’s Vineyard
A brief ferry ride or flight brings your family to Martha’s Vineyard, a small island just off the coast. This upscale vacation destination offers several beaches, including Lighthouse Beach and Owen Park Beach. See where most of the film “Jaws” was shot with a visit to the Joseph Sylvia State Beach. Biking is one of the best ways to see the island, and Martha’s Vineyard Bike Rentals can set your family up with bikes for the entire weekend. Kids want to ride over and over again on the authentic Coney Island carousel at the Flying Horses Carousel.
Find vacation rentals in Martha’s Vineyard
Breathe in the fresh sea air from your vacation rental with stunning sea views on the island of Nantucket just off the coast of Cape Cod. With Val’s Tours of Nantucket, you see all the highlights of the island and several of the island’s lighthouses, including Green Point Light and Sankaty Head Light. Learn more about the island’s rich history as a whaling community at the Nantucket Whaling Museum. Check the schedule and see a performance at the Dreamland Film and Performing Arts Center. Performances range from ballets to indie movies.
Find vacation rentals in Nantucket
Take advantage of the first days of summer in Amherst with its easy access to the Mount Holyoke Range State Park. The views on the Seven Sisters hiking trail are even more beautiful than advertised as you make your way along this eight-mile trail with numerous overlooks. Kids love taking a tour of the Eric Carle Museum of Picture Book Art and seeing all the cool pictures from their favorite stores while the classical reader in your family must visit the Emily Dickinson Museum in the author’s former home.
Find vacation rentals in Amherst
See the first Pilgrim settlement from 1620 with a visit to Plymouth. Of course, you have to see Plymouth Rock with a visit to the Pilgrim Memorial State Park. It was here that the Mayflower landed and colonization in Massachusetts began. You can also see a replica of the Mayflower and image what it must have been like sailing the Atlantic Ocean as a passenger. Kids love a visit to Plimoth Plantation, where the docents dress in period costumes and provide you a glimpse of what life was like in the 1600s.
Find vacation rentals in Plymouth
Smell the sea breeze with a vacation rental close to the water in Barnstable. This area has a long history with the sea, and the shoals offshore pose a danger to boats. Learn more about the history of shipwrecks and those that protect sailors at the Coast Guard Heritage Museum and the Cape Cod Maritime Museum. Let the kids sail a ship or drive a train at the Cape Cod Children’s Museum. Gaze in wonder at the beautiful lighthouses that dot the coastline with a cruise from Bay Spirit Tours.
Find vacation rentals in Barnstable
Ready to go? Check out these amazing Massachusetts vacation rentals on Tripping.com.