Boston events for May 2017. Best festivals, fun things to do, weekend street fairs, kids activities, and free entertainment in Boston, Massachusetts.

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Best events for 12 months
May 2017
May 2017

Enjoy the best Boston events, festivals, and things to do with this calendar of events.

Mileage is from Faneuil Hall in downtown Boston, Massachusetts.

Flowers & art

May 1, 2017 (begins April 29)

2.6 miles SW

Art in Bloom is a festival of floral arrangement and fine art that includes classes, demonstrations, walking tours, teas, a preview party, and a family-friendly Community Day on Sunday at the Museum of Fine Arts.

Film festival

May 1 - 3, 2017 (begins April 26)

Boston locations

The Independent Film Festival Boston (IFFBoston) shows about 100 innovative crowd-pleasing films, holds frequent parties, invites filmmakers to attend panel discussions, and has an awards ceremony.


May 1 - 7, 2017 (begins April 28)

Greater Boston

ArtWeek Boston offers dozens of creative experiences, artist talks, performances, behind-the-scenes tours, and kids’ activities. Many are free. Repeats in Sept.

Steampunk festival

May 6, 2017

12 miles west

Watch City Steampunk Festival includes Victorian calliopes, Penny Farthings, costumed performers, musicians, bands, lectures, an open-air market with Steampunk vendors, and a parade in Waltham. Free.

Monster trucks

May 6 - 7, 2017

54 miles NW

Big trucks with big wheels create big noise and excitement at Monster Jam at Verizon Wireless Arena in Manchester, NH.

Charity walk

May 7, 2017

1 mile SW

Join 40,000 people on the 10-mile Walk for Hunger and 5K run, which begin on Boston Common.

MayFair at Harvard Square

May 7, 2017 (rain date May 21)

3.6 miles west

MayFair offers four stages of entertainment, chalk art, beer gardens, and vendors of food, art, jewelry, and clothing at Harvard Square. Free. (Postponed from May 1 to May 15 due to rain.)

Japanese festival

May 13, 2017 (uncertain)

4.5 miles SW

The Brookline Cherry Blossom Festival features Japanese music, food, taiko drumming, bon odori festival dancing, crafts, and games at Brookline High School. Donation.

Craft fair

May 13, 2017

23 miles north

Shop from 150 vendors at Andover Crafts in the Park.

Mother’s Day restaurants

May 14, 2017

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.

Mother’s Day cruise

May 14, 2017

0.4 miles east

Mother’s Day Brunch Cruise includes a brunch buffet, views of Boston Harbor, and a rose for Mom for $60.

Duckling parade

May 14, 2017

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.

Mother’s Day comedy

May 14, 2017

4.5 miles NW

The Boston Comedy Chicks tell jokes about motherhood at their Mother’s Day Comedy Show at The Center for Arts at the Armory in Somerville.

Lilac day

May 14, 2017

5.4 miles SW

Lilac Sunday features tours of the lilacs and other collections, live music, family activities, food trucks, and picnicking at the Arnold Arboretum. Free.

Nantucket Wine Festival

May 17 - 21, 2017

112 miles SE via ferry

Nantucket Wine Festival offers 60 events, including tastings, seminars, meals, and marketplaces.

Kite and Bike Festival

May 20, 2017

6 miles SE

Buy a kite and borrow a free bike at the Kite and Bike Festival in Franklin Park Playstead, or bring your own.

Boston Calling music festival

May 26 - 28, 2017

0.1 miles west

Family friendly Boston Calling has outdoor stages for big-name music acts at City Hall Plaza. Repeats in Sept.

Campfire music festival

May 26 - 29, 2017

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.

Memorial Day Parade

May 28, 2017

3 miles NW

Watch marching bands, veterans’ groups, and beauty queens in the Memorial Day Parade that begins at Somerville City Hall and goes up Highland Avenue to Veterans Memorial Cemetery at 1330 Broadway. Free.

Beverage festival

May 2017 (undated)

multiple locations

Thirst Boston features cocktail seminars, tastings, and parties for beverage enthusiasts and industry insiders.

Bike week

May 2017 (undated)

Greater Boston area

Find bike rodeos, rides, breakfasts, and workshops offered during Bay State Bike Week. Some events start May 1.

Cinco de Mayo pub crawl

May 2017 (undated)

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 2017 (undated)

Greater Boston locations

Jazz Week offers numerous jazz events, from solo shows to jazz ensembles, and some are free.

Music concert

May 2017 (undated)

1.2 miles west

EarthFest is a popular outdoor concert that includes environmental exhibits, healthy food vendors, and a separate kids’ stage at the Hatch Shell on the Charles River. Free.

Beer festival

May 2017 (undated)

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.

Symphonic concert

May 2017 (undated)

2 miles west

Berklee Symphonic Winds Spring Concert features works for winds, brass, and percussion at the Berklee Performance Center. Repeats in Dec. Free.

Comedy competition

May 2017 (undated)

2.6 miles west

Vote for your favorite Boston standup comics in the final round of the month-long StandUp ThrowDown tournament at ImprovBoston.

Bike parade

May 2017 (undated)

3.3 miles SW

Ride five miles on Beacon Street with no cars and a police escort in the Brookline Bicycle Parade, which has adult and child versions that begin and end at Amory Park, with a party afterward. Free.

Music festival

May 2017 (undated)

Cambridge locations

Together Boston celebrates music, art, and technology with performances, films, exhibits, and educational panels in Cambridge.

Cinco de Mayo Festival

May 2017 (undated)

5.5 miles NE

The Cinco de Mayo Festival features food, festive entertainment, and drinks in Winthrop.

Wine and chocolate

May 2017 (undated)

6 miles north

Enjoy wine, sparkling juice, appetizers, and desserts at Friends of the Malden Public Library Wine Tasting and Chocolate Buffet, with live piano music.

Cinco de Mayo at WGBH

May 2017 (undated)

7.2 miles west

Enjoy Mexican food, drink, and music at WGBH Celebrates Cinco de Mayo, and hear professors explain the significance of the holiday at WGBH Studios.

Home tour

May 2017 (undated)

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.

Bluegrass festival

May 2017 (undated)

30 miles SE

Bluegrass on the Bogs [sound] is an acoustic non-traditional bluegrass festival with local bands, food and craft vendors, workshops, kids’ events, and camping at Camp Kiwanee in Hanson.

Run in the mud

May 2017 (undated)

40 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.

Vegetarian festival

May 2017 (undated)

44 miles west

Discover new food items, taste samples, speak to producers, and shop at the New England VegFest at the DCU Center in Worcester. Free.

Renaissance fair

May 2017 (undated)

48 miles north

New Hampshire Renaissance Faire is a laid-back event with craft and food vendors, wandering musicians, theater on stage, and knights jousting in a field in Kingston, NH.

Short play festival

May 2017 (undated)

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.

Mother’s Day wine/chocolate

May 2017 (undated)

4.8 miles SW

Mother’s Day Wine & Chocolate includes a two-hour class about wine and chocolate from Boston Wine School, a tasting, and a dinner with wine in Brookline.

Stories about motherhood

May 2017 (undated)

5.1 miles SW

Listen To Your Mother celebrates and validates motherhood with readings that are touching and humorous at Hope Central Church in Jamaica Plain.

Mother’s Day memorial

May 2017 (undated)

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.

Mother’s Day tea

May 2017 (undated)

10 miles west

Take Mom to Mother’s Day Tea at Gore Place to have tea and cake and hear a talk about tea in a beautiful 1806 mansion in Waltham.

Mother’s Day cupcakes

May 2017 (undated)

14 miles SW

Decorate six jumbo cupcakes either with or for Mom at Mother’s Day Cupcake Decorating Class at Treat Cupcake Bar in Needham for $75 per person.
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© May 2017 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts. bos-05