Boston events May 2019. Things to do in Boston.

Best events for 12 months

Boston events May 2019

Film festival

May 1, 2019
(begins April 24)
Boston locations
The Independent Film Festival Boston (IFFBoston) shows nearly 100 innovative crowd-pleasing films, invites filmmakers to attend panel discussions, and has an awards ceremony.


May 1 - 5, 2019
(begins April 26)
Greater Boston
ArtWeek offers hundreds of artist talks, creative experiences, performances, behind-the-scenes tours, and kids’ activities. Many are free.

Funny women

May 2 - 5, 2019
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.

Arts festival

May 2 - 5, 2019
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.

Hip festival & parade

May 4, 2019
(noon to 6 p.m.)
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.

Art walk

May 4 - 5, 2019
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.

Cinco de Mayo pub crawl

May 5, 2019
0 miles
Cinco de Mayo Pub Crawl Boston includes drink specials at the Hard Rock Cafe and Mija Cantina at Faneuil Hall.

Charity walk

May 5, 2019
1 mile SW
Join 40,000 people on the 20-mile Walk for Hunger and 5K run, which begin on Boston Common.

MayFair at Harvard Square

May 5, 2019
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.

Japanese festival

May 11, 2019
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.

Steampunk festival

May 11, 2019
12 miles west
Watch City Steampunk Festival has 65 vendors, kids’ activities, food trucks, and costumed performers at Waltham Common. Free.

Mother’s Day restaurants

May 12, 2019
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 12, 2019
1 mile SW
Families celebrate the Boston-based book “Make Way for Ducklings” by wearing yellow and registering to join the Duckling Day Parade at Boston Public Garden, rain or shine.

Mother’s Day memorial

May 12, 2019
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.

Nantucket Wine Festival

May 15 - 19, 2019
112 miles SE via ferry
Nantucket Wine Festival offers 70 events, including tastings, seminars, meals, and marketplaces.

Quilt show

May 17 - 18, 2019
11 miles west
See 150 quilts that range from classic to cutting-edge at Quilters’ Connection Quilt Show, which has guided tours and demonstrations of quilting techniques at St. James Erebuni Armenian School in Watertown.

Kite and Bike Festival

May 18, 2019
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.

Short play festival

May 19, 2019
1.5 miles SW
See the best 50 plays shorter than 10 minutes, out of 400 entries by New England playwrights, at Boston Theater Marathon at Boston Center for the Arts.

Memorial Day Parade

May 19, 2019
3 miles NW
Watch marching bands, veterans’ groups, and beauty queens in the Memorial Day Parade that begins at Somerville City Hall and goes down Highland Avenue and then Holland Street. Free.

Boston Calling music festival

May 24 - 26, 2019
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. Repeats in Sept.

Campfire music festival

May 24 - 27, 2019
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 Aug.

Greek festival in Arlington

May 30 - June 2, 2019
7.8 miles NW
Arlington Greek Festival offers Greek food, beer, wine, music, dancing, and kids’ activities at St. Athanasius the Great Greek Orthodox Church in Arlington. Free.

Celebrity food festival

May 31, 2019
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.

Adventure race

May 2019
location uncertain
Questival is a 24-hour race that begins with a check-in party. Your team of 2 to 6 people completes the challenges assigned by a smartphone app to win prizes. Video.

Bike week

May 2019
Greater Boston area
Find bike rodeos, rides, breakfasts, and workshops offered during Bay State Bike Week.

Return of the Swans

May 2019
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 festival

May 2019
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.

Lamb tasting

May 2019
1.6 miles south
Taste lamb and BBQ cooked by six local chefs, and sample beer, wine, and spirits at Boston Lamb Jam, with butcher demonstrations and live music at the SoWa Power Station for age 21+.

Comedy for a cause

May 2019
2.4 miles west
Boston celebrities and politicians ham it up in skits and songs about pop culture at Banned in Boston at House of Blues, preceded by cocktails at Lansdowne Pub. The pricey tickets support charity.

Comedy competition

May 2019
2.6 miles west
Vote for your favorite Boston standup comics in the semi-finals or finals of the month-long StandUp ThrowDown tournament at ImprovBoston.

Technology party

May 2019
3.6 miles SW
Join tech community professionals at BostInno de Mayo for margaritas, appetizers, and networking at Lansdowne Pub for age 21+. Your ticket includes food and one drink.

Bicycle film festival

May 2019
7.6 miles NW
See 8 short films about bicycling worldwide, with a cookie buffet and live band at the Bike Travel Film Festival at Regent Theatre in Arlington.

Home tour

May 2019
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.

Run in the mud

May 2019
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.

Kids’ obstacle race

May 2019
47 miles west
Kids 5 to 16 run through mud and over obstacles during the Kids Obstacle Challenge at Kalon Farm in Lancaster. Parents can race for free.

Mother’s Day cruise

May 2019
0.4 miles east
A Mother’s Day cruise includes a brunch or dinner buffet, views of Boston Harbor, and a flower for Mom.

Lilac day

May 2019
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.
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