Boston events May 2020. Things to do in Boston.

Best events for 12 months

Boston events May 2020

Arts festival

May 1 - 3, 2020
(begins April 30)
3.5 miles NW
Arts First celebrates student and faculty creativity with 150 music, theater, dance, film, and visual arts events at Harvard University, including 100 stage performances on Saturday from 1 to 5 p.m. Free.


May 1 - 10, 2020
Greater Boston
ArtWeek offers hundreds of artist talks, creative experiences, performances, behind-the-scenes tours, and kids’ activities. Many are free.

Vaudeville musical

May 1 - 17, 2020
8.2 miles NW
With its show-stopping songs, Gypsy “may be the greatest of all American musicals” says The New York Times. See it live in Arlington.

Discount tickets $12.50

Hip festival & parade

May 2, 2020
4.4 miles SW
Celebrate Spring’s return at Wake Up the Earth Festival, with an 11 a.m. people’s parade, six performances stages, craft booths, and food vendors at SW Corridor Park (between New Minton Street & Lawndale Terrace). Rain date is Sunday. Donation.

Home tour

May 2, 2020
17.2 miles SW
Wellesley Kitchen and Home Tour features a ticketed tour of six different houses in Wellesley, with gourmet bites and an opportunity to meet the interior designers and landscape architects for age 18+. No photos.

Art walk

May 2 - 3, 2020
1.4 miles SW
Meet 100 artists in their studios and view gallery exhibits during the self-guided SoWa Art Walk. The SoWa Open Market also is open on Sunday. Free.

Flowers & art

May 2 - 4, 2020
2.6 miles SW
Art in Bloom is a festival of floral arrangement inspired by art, with exhibitions in galleries, walking tours outdoors, classes, demonstrations, and family-friendly Community Day on Sunday at Museum of Fine Arts.

Charity walk

May 3, 2020
1 mile SW
Join 40,000 people on the 20-mile Walk for Hunger and 5K run, which begin on Boston Common.

New song competition

May 4, 2020
2 miles west
Writers pitch their songs to 10 vocalists, who perform with a band before a panel of judges to win prizes at Perfect Pitch Concert at Berklee Performance Center.

Funny women

May 7 - 10, 2020
Boston & Cambridge
Women in Comedy Festival (WICF) includes acclaimed stand-up comedians, improv & sketch groups, musical comedy groups, and solo artists and storytellers. It also offers a variety of comedy workshops and panels.

Steampunk festival

May 9, 2020
12 miles west
Watch City Steampunk Festival has 65 vendors, kids’ activities, food trucks, and costumed performers at Waltham Common. Free.

Renaissance fair

May 9 - 10 and 16 - 17, 2020
54 miles north
Family-friendly New Hampshire Renaissance Faire has craft and food vendors, wandering musicians, theater on stage, fanciful fairies, and knights jousting on a farm in Fremont, NH.

Mother’s Day restaurants

May 10, 2020
New England locations
OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day. We also recommend checking the list of Mother’s Day restaurants at BostonChefs.

Duckling parade

May 10, 2020
1 mile SW
Families celebrate the Boston-based book “Make Way for Ducklings” by registering to join the Duckling Day Parade, which begins on the Boston Common at the Parkman Bandstand and ends in the Public Garden near the famous bronze duck statues, rain or shine. Wear yellow, and enjoy playtime 10 a.m. to noon.

Lilac day

May 10, 2020
5.4 miles SW
Lilac Sunday features tours of the lilacs and other collections, family activities, and picnicking (bring your own food) at the Arnold Arboretum. Free.

Mother’s Day memorial

May 10, 2020
6.5 miles west
Visit the graves of notable mothers and see symbols of motherhood on monuments during the Memories of Mothers tour at Mount Auburn Cemetery.

Food festival in Nantucket

May 13 - 17, 2020
112 miles SE via ferry
Nantucket Wine & Food Festival offers 70 events, including tastings, seminars, meals, and marketplaces.

Jazz festival

May 14 - 17, 2020
7.9 miles NE
Arlington Jazz Festival has concerts on four days, with the main event Sunday evening at Arlington Town Hall.

Art fair

May 15 - 17, 2020
1.5 miles SW
See contemporary art made by 90 juried artists at the CraftBoston Spring show in the Cyclorama at Boston Center for the Arts. Held in May and December.

Discount tickets $7.50

Japanese festival

May 16, 2020
(12 to 4 p.m.)
5 miles SW
The Brookline Cherry Blossom Festival features Japanese music, food, taiko drumming, bon odori festival dancing, crafts, and games at Brookline High School. Lawn chairs and blankets welcome. Donation.

Kite and Bike Festival

May 16, 2020
6 miles SE
Buy a kite and borrow a free bike at the Kite and Bike Festival on Franklin Park Golf Course, or bring your own.

Run in the mud

May 16, 2020
38.6 miles NW
Run through the wet and muddy 5K obstacle course in Devens called Muckfest both for the fun of it and to support charity at Willard Athletic Complex in Devens.

BBQ in Lexington

May 16 - 17, 2020
13.9 miles NW
Lexington Battle Green BBQ Festival promises “local barbecue vendors, up-and-coming craft breweries, and great live bands” playing blues, funk, R&B, and rock and roll.

MayFair at Harvard Square

May 17, 2020
3.6 miles west
MayFair offers three stages of entertainment, chalk art, beer gardens, and vendors of food, crafts, and jewelry at Harvard Square. Free.

Boston Calling music festival

May 22 - 24, 2020
5.6 miles west
Family friendly Boston Calling has outdoor stages for big-name music acts in the Harvard Athletic Complex at 65 N. Harvard Street in Allston.

Campfire music festival

May 22 - 25, 2020
3.6 miles NW
Hear new performers and watch songwriters interact and swap tunes as they sing in the round at the Campfire Festival at Club Passim. Repeats in Sept.

Wine at the zoo

May 30, 2020
(5 to 7:30 p.m.)
3.5 miles SW
Sample wines at Roars and Pours as you stroll past animals in the Tropical Forest Pavilion at Franklin Park Zoo for age 21+.


May 31, 2020
1.4 miles SE
Watch “the world’s fastest men and women” jump and sprint up Boylston Street during Boost Boston Games (1:30 to 6 p.m.), or register to run yourself in the all-ages Boost Back Bay Mile (11 a.m. to noon).

Bike week

May 2020
Greater Boston area
Find bike rodeos, rides, breakfasts, and workshops offered during Bay State Bike Week.

Cinco de Mayo pub crawl

May 2020
0 miles
Cinco de Mayo Pub Crawl Boston includes drink specials at the Hard Rock Cafe and Mija Cantina at Faneuil Hall.

Jazz Week

May 2020
Greater Boston locations
Jazz Week offers numerous jazz events, from solo shows to jazz ensembles, and some are free.

Return of the Swans

May 2020
0.8 miles SW
The Return of the Swans from their winter home at Franklin Park Zoo to the lagoon in Boston Public Garden includes a parade with a brass band, a ceremony, and children’s activities. Free.

Beer tasting

May 2020
1.2 miles SW
Taste beer from the 60 brewers who run the Power Beer Fest, with food truck fare for sale at the Castle at Park Plaza for age 21+.

Beer festival

May 2020
1.5 miles SE
Catch a shuttle from South Station to Harpoon Brewery to enjoy beer, great food, and live local music at HarpoonFest. Tickets at the door.

Celebrity food festival

May 2020
5.2 miles west
Guy Cooking with Best Buddies is a celebrity chef festival that includes food from 30 local chefs, wine, beer, entertainment, and Guy Fieri from Food Network in the Murr Center at Harvard Stadium.

Mother’s Day cruise

May 2020
0.4 miles east
A Mother’s Day cruise includes a buffet, views of Boston Harbor, and a flower for Mom.

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