Top Things to Do in Boston This May

• Boston Ballet
• Recurring daily

The 2025 Spring Experience program combines three sublime ballets that showcase the breadth and beauty of ballet today. Alongside Mikko Nissinen’s brilliantly reimagined Raymonda , the program includes two beloved works of Jiři Kylián, who is the among the most revered…

• Boston Lyric Stage
• Recurring weekly on Sunday, Wednesday, Thursday, Friday, Saturday

Brimming with classic musical theater tunes, endearing characters, and good-humor all around, Hello Dolly! is the perfect balm for the soul. With a twinkle in her eye, Dolly Levi orchestrates matters of the heart for those looking for love as the incomparable matchmaker that she…

• Boston Harbor City Cruises
• Recurring daily

Set sail with us for the whale watch experience of a lifetime. Our destination: Stellwagen Bank Marine Sanctuary, a rich feeding ground for whales, dolphins, sea birds and other marine creatures. You’ll have a good chance to view several different species of large whales…

• Soldiers & Sailors Monument, Boston Common
• Recurring daily

Home Base and Massachusetts Military Heroes Fund invite you to help create Boston’s iconic Memorial Day Flag Garden tribute. Each of the 37,000+ American flags planted at the Soldiers and Sailors Monument this Memorial Day will represent every brave Massachusetts service member…

• Boston Calling Music Festival
• Recurring daily

More than 50 performances across 4 outdoor stages, the best food in Boston, 100 foot Ferris wheel, art installations, life-size games, and other exciting activities. There’s so much to explore and see at Boston Calling. Over 30 all-star food vendors, local and international…

• The Skating Club of Boston, Norwood

Don't miss Stars on Ice at The Skating Club of Boston in Norwood on May 24 and 25! Come see this Rock Star list of skaters!: Ilia Malinin Madison Chock & Evan Bates Elvis Stojko Alysa Liu Isabeau Levito Amber Glenn Jason Brown Satoko Miyahara Keegan Messing Maxim Naumov TWO…

• Boston Symphony Orchestra / Boston Pops / Symphony Hall
• Recurring weekly on Saturday

Fearless optimist, Princess Anna, sets off on an epic journey – teaming up with rugged mountain man, Kristoff, and his loyal reindeer Sven – to find her sister Elsa, whose icy powers have trapped the kingdom of Arendelle in eternal winter. Encountering Everest-like…

• Soldiers and Sailors Monument, Boston Common

Join Hub Town Tours as we commemorate the anniversary of the Massachusetts 54th Regiment departing Boston in 1863. The first Black regiment from the North left Boston under the command of Col. Robert Gould Shaw after a parade through town attended by thousands of local residents…

• Fenway Park

Live Nation and the Boston Red Sox are excited to welcome Shakira to America's Most Beloved Ballpark on Thursday, May 29, 2025. The show is part of the Nucar Fenway Concert Series presented by Wasabi Technologies.

• Various Locations
• Recurring daily

The North America (NORAM) Cup is a biennial gay and inclusive rugby tournament, and the largest rugby union tournament in North America. The inaugural NORAM Cup was in 2023, hosted by the Charlotte Royals in North Carolina. The host city and club for the 2025 tournament is…

• The Stage at Suffolk Downs

Teddy Swims is a lover. The 29-year-old artist, who merges honeyed soul with raucous rock energy and pleasing pop hooks, writes nearly all his songs about falling in or out of romantic entanglements. He zeroes in his focus on his latest EP, Tough Love—a six-song collection of…