Events

10 free things to do in Boston in May

From colorful festivals to outdoor concerts to world-famous art.

The 2026 Wake Up The Earth Festival will take place May 2 in Jamaica Plain. Wake Up the Earth Fest

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With April showers potentially done, Boston is now blooming with May flowers and things to do. Get out and enjoy the city with this guide of fun (and often outdoor) springtime activities. The best part — you can enjoy all of it without spending a dime.

Here are 10 things to do in Boston for free this May.

1. Attend an outdoor concert

Berklee College of Music students, faculty, and alumni perform in more than 200 free outdoor concerts all over the city during the Berklee Summer in the City series taking place between May and September. Guests can enjoy everything from jazz to classical, Latin to funk, and folk to world. Concert locations include Atlantic Wharf, the ICA, the Prudential Center, Spectacle Island, Club Passim, Longfellow House, and South Boston Maritime Park. This year’s series will also include the Tito Puente Latin Music Series, Sunset Concerts, Swinging in the Fens, and Jazz at the Fort, to name a few. (Various locations throughout Boston)

2. Celebrate spring

Every first Saturday in May, thousands head to Jamaica Plain to dance, parade,
create, and honor the Boston neighborhood’s history of activism, expression, and inclusion during Wake Up The Earth Festival. Entering its 48th year and planned for May 2, the celebration represents the beginning of spring with festivities that kick off with a parade at around 11 a.m., with folks gathering at Curtis Hall and moving through the community. (20 South St., Boston)

3. Learn about Boston’s most famous stripper

Not your typical evening at the Boston Public Library, former exotic dancer and performer Lucy Wightman discusses her 2025 memoir, “Princess Cheyenne: My Life as Boston’s Most Famous Stripper,” during an event on May 6 from 6 to 7 p.m. Her tales recount how the debutante from Lake Forest, Ill., ended up in Boston’s notorious “Combat Zone,” got engaged to Cat Stevens,
traveled and performed with Andy Kaufman, and more throughout her wild
career as the legendary “Socialite Stripper.” (700 Boylston St., Boston)

4. Test your history smarts

Put your Boston history knowledge to the test at Road to 250 Trivia Night, a
special history-themed monthly competition celebrating America’s
250th anniversary at Spy Bar inside The Revolution Hotel. With three
dates on the calendar — May 6, June 3, and July 1 — doors open at 6 p.m. and
trivia begins at 7 p.m. There will fun giveaways, prizes, food and drink specials to purchase, and maybe even a surprise visit from a founding father. Participation is free and no advance sign-up is required, but feel free to register here. (40 Berkeley St., Boston)

5. Stroll by blooming lilacs

Locals and visitors alike excitedly wait all year for America’s first arboretum to
host its famous annual Lilac Sunday event — an enjoyable outdoor event since 1908. Guests of the Arnold Arboretum enjoy tours of one of the premier lilac
collections in North America (the arboretum boasts more than 407 lilac plants of 173 kinds), as well as family activities, displays, food vendors, and picnicking (on this special day only) on May 10 from 10 a.m. to 3 p.m. (125 Arborway, Boston)

Lilac Sunday at the Arnold Arboretum. *Arnold Arboretum*

6. Watch little ‘ducks’ all in a row

Spring has sprung when the ducklings come out to play during another beloved Mother’s Day event in Boston on May 10. Families celebrate the Boston-based book “Make Way for Ducklings.” Every year, more than 1,000 children dress up as feathered friends and gather on Boston Common to enjoy face painting, a puppet show, and marching behind the famous Harvard Band to the Public Garden. Registered families get a goody bag. (Boston Common, Boston)

7. Go fly a kite

A 50-year tradition that commemorates the opening day of Franklin Park, the Kite & Bike Festival gathers more than 1,000 people each May for picnicking, kite flying, riding bikes, and music. Held on May 16 from noon to 4 p.m., the day is packed with activities and the sky is filled with kites (you can make one there, buy one, or bring your own). There will be food trucks, bikes from Countdown to Kindergarten to try for younger kids, and a bicycle repair station by REI. (Franklin Park Playstead, 25 Pierpont Rd., Boston)

8. Immerse yourself in postal history

The 12th international philatelic (aka the study and collection of postage stamps, postal history, and related materials) exhibition gathers at the Boston Convention & Exhibition Center during Memorial Day week (May 23-30). Sponsored by the USPS and set within a 352,000-square-foot exhibition area, Boston 2026 will host more than 1,000 fascinating displays and 300-plus lectures on all sorts of topics (many of them provided by the Smithsonian Institution). (415 Summer St., Boston)

9. Reflect on those who gave their lives

As part of the Memorial Day Weekend events held on May 25 throughout Boston, a spectacular sight is the Garden of Flags at Boston Common’s Soldiers and Sailors Monument. Each of the 37,000-plus flags planted by
the Massachusetts Military Heroes represents a Massachusetts service member who bravely gave his or her life defending our country since the Revolutionary War. (Boston Common, Boston)

10. Surround yourself with world-famous art

Local museums will offer family-oriented festivities this year with special exhibitions and free admission on Memorial Day. One such event is the MFA’s open house on May 25 from 10 a.m. to 5 p.m. in the Shapiro Family Courtyard where you can make art and music, watch a film, and join tours and discussions in the art galleries. Please note, free admission is for Massachusetts residents only. (465 Huntington Ave., Boston)

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