May in Boston is a time of awakening. Summer is just starting to arrive in the city, which means the return of open-air markets, outdoor festivals, and warm weather activities. The flowers are blooming, the whales are arriving back in the waters around the city, and the Green Monster is awaiting you at Fenway Park.
Planning a trip to Boston in May? We’ve compiled a list of the best things to do in Boston in May, from a one-of-a-kind music festival to the cutest Mother’s Day celebration you’ve ever seen. Pick your favorite springtime activities, and you’re bound to have an unforgettable May vacation in this historic city!
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The 15 Best Things to Do in Boston in May
1. Rock Out at Boston Calling
Boston Calling is one of the biggest and best events in Boston in May. Taking place over Memorial Day weekend at the Harvard Athletic Complex, this three-day, four-stage outdoor music festival brings about the best in music. It’s an eclectic mix of rappers, alternative bands, rock stars, pop stars, and more.
In addition to the music, guests can also enjoy food from more than 30 vendors, incredible visual arts displays, and a 100-foot Ferris wheel.
2. Take a Whale-Watching Tour
Boston Harbor City Cruises offers whale-watching tours starting every year around mid-May, making this unique activity one of the most memorable things to do in Boston in May. You’ll set sail for Stellwagen Bank National Marine Sanctuary, a feeding ground for not only whales but also dolphins, sea birds, and much more.
Prime whale-watching season in Boston lasts from May to October as whales migrate to the North Atlantic for summer. During this whale-watching tour, New England Aquarium naturalists will be on hand to tell you everything there is to know about the animals you’ll spot.
3. See a Red Sox Game
If you’re in Boston in May, you’re there at a perfect time to catch the Red Sox play. Fenway Park, which is the oldest ballpark in the MLB, is unlike any other stadium. There’s so much history here. Even if you’re not a huge baseball fan, seeing a game at Fenway Park is still an experience you’re not going to want to miss.
4. Show Your Respect at the Garden of Flags
Memorial Day arrives each May, and in Boston, it arrives with the Garden of Flags. Hundreds of volunteers come together the week of Memorial Day to plant a garden filled with American flags in the Boston Common at the Soldiers & Sailors Monument.
The result is a sea of more than 37,000 flags, symbolizing every Massachusetts service member who gave their lives in the act of service since the Revolutionary War. If you’re in Boston in May, be sure to stop by to pay your respects.
5. See the Duckling Day Parade
It goes without saying that Mother’s Day is another one of the biggest events in Boston in May, but it also goes by another name: Duckling Day! On Mother’s Day, Boston’s parks are home to a celebration honoring the beloved children’s book “Make Way for Ducklings.”
Hundreds of children gather together and dress as the characters from the book to parade around Boston, starting at the Boston Common and ending at the Public Garden. Before the parade, the Common is where you’ll find plenty of interactive family programming, from circus-themed games to a creative play area.
6. Stop by the MFA Boston for Free
The Museum of Fine Arts Boston (MFA Boston) is what to do in Boston in May if you’re looking for a way to experience its more than 100 galleries for free. Admission to the museum is free for four days out of the year: Martin Luther King Jr. Day, Memorial Day, Juneteenth, and Indigenous Peoples’ Day. With Memorial Day arriving in May, you’ll definitely want to pay the MFA Boston a visit if you’re visiting Boston in May.
7. Check Out the Downtown Boston Arts Market
Want to immerse yourself in the arts scene in Boston? May kicks off the Downtown Boston Arts Market, located at Downtown Crossing. If you’re looking to pick up some trinkets during your trip, visiting this market is one of the best things to do in spring in Boston.
Running every Thursday and Friday, you can check out all sorts of artisan goods, from jewelry to woodworking to metal sculptures.
8. Enjoy Lilac Sunday at the Arnold Arboretum
Lilac Sunday is another of the best events in Boston in May, and it also takes place on Mother’s Day. When you visit the Arnold Arboretum on Mother’s Day, you’ll be visiting when hundreds of lilacs are in peak bloom. You can take a self-guided tour or get a tour with one of the on-site experts.
While you can see these lilacs during other days in May, going on Lilac Sunday means also getting to enjoy interactive children’s programming, as well as picnics, which are generally not allowed at the arboretum on other days.
9. Stop by the Greenway Artisan Market
The Greenway Artisan Market is one of the best things to do in Boston in spring. Taking place at the Rose Kennedy Greenway, this open-air market invites local artisans and craftspeople to share their work, resulting in an incredible array of art, local goods, and unique products.
The market runs every Saturday starting in early May through October. Beginning in June, the market will also run on Sundays.
10. Chow Down at the Greenway Food Truck Festival
Starting in April, the Rose Kennedy Greenway becomes home to a rotating list of all different sorts of Boston food trucks. But in May, these food trucks all come together for one big food festival.
The Greenway Food Truck Festival typically arrives in early May, and with it comes an eclectic mix of local treats, from giant cookies to dumplings and everything in between.
11. Check Out the Films of IFFBoston
The Independent Film Festival Boston (IFFBoston), one of the best events in Boston in May, typically arrives every spring. It brings a diverse array of independent programming to art-house cinemas throughout Boston and the surrounding areas, featuring more than 120 screenings and discussions with the film’s directors.
It’s a film festival that truly allows you to immerse yourself in the art of filmmaking, all while surrounded by storytellers who want to share diverse voices and points of view. Today, it’s the largest film festival in New England.
12. Enjoy Free Concerts from the Berklee College of Music
Looking for free things to do in Boston in May? Check out the free concerts put on by the Berklee College of Music starting every May. The Berklee Summer in the City concerts feature performances by students, alums, and faculty at locations throughout the Greater Boston area. Concerts run through September.
13. Get Your Drink on at HarpoonFest
Celebrate the anniversary of Harpoon IPA at Harpoon Brewery’s HarpoonFest, one of the best events in Boston in May. This annual music and beer festival brings you DJs, cover bands, Boston’s best food trucks, and all the beer, cider, and hard seltzer you could want. This two-day party is sure to make your May all the more fun!
14. Revel in the Shows of the Boston Theater Marathon
Live theater lover? Then, the Boston Theater Marathon is a must-do if you’re spending May in Boston. Produced by Boston Playwrights’ Theatre, this all-day marathon sees the production of all new 10-minute plays.
The plays are selected from over 400 entries from playwrights all over New England, resulting in 50 selected productions that are the best of the best. You just may discover your new favorite writer!
15. Enjoy the return of the SoWa Open Market
If you’re wondering what to do in Boston in May, the SoWa Open Market returns every May and runs every Sunday through October. As one of the largest open-air farmer and artist markets in Boston, you never know what treasure you’ll uncover here. From food trucks to masterpieces from local artists, there’s so much to see and do at this beloved market!
There you have it! The 15 best things to do in Boston in May. What are your favorite events in Boston in May? Let us know in the comments!
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