Boston events for May 2016. Best festivals, fun things to do, weekend street fairs, kids activities, and free entertainment in Boston, Massachusetts.

Best events for 12 months
Best events for 12 months
May 2016
May 2016

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

Mileage is from Faneuil Hall in downtown Boston, Massachusetts.

Jazz Week

May 1, 2016 (begins April 22)

Greater Boston locations

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

Charity walk

May 1, 2016

1 mile SW

Join 40,000 people on the Walk for Hunger, which begins at Boston Common and goes up to 20 miles.

Art fair

May 1, 2016 (begins April 29)

1.5 miles SW

See the contemporary work of 90 juried artists at the CraftBoston Spring show in the Cyclorama at Boston Center for the Arts. Discount tickets $10.

Arts festival

May 1, 2016 (begins April 28)

3.5 miles NW

Arts First celebrates student and faculty creativity with more than 200 music, theater, dance, film, and visual arts events at Harvard University. Most are free.

MayFair at Harvard Square

May 1, 2016 (rain date May 15)

3.6 miles west

MayFair offers five stages of entertainment, chalk art, beer gardens, and vendors of food, art, jewelry, and clothing at Harvard Square. Rain date May 15. Free.

Visit art studios

May 1, 2016 (begins April 30)

4.2 miles SW

Visit 35 artists’ studios and homes in the Brookline area during Open Studios weekend sale. Free.

1960s rock musical

May 1, 2016 (begins April 15)

20 miles NW

Tony Award winner Hair features the music, culture, and controversy of hippies who oppose the Vietnam War at Umbrella Center for the Arts in Concord. Nudity. Discount tickets $13.

Vegetarian festival

May 1, 2016

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.

Flowers & art

May 1 - 2, 2016 (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 Sunday Family Day at the Museum of Fine Arts.

Film festival

May 1 - 4, 2016 (begins April 27)

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 - 8, 2016 (begins April 29)

Greater Boston

ArtWeek Boston offers 100+ creative experiences, artist talks, performances, behind-the-scenes tours, and kids’ activities. Many are free. Repeats in Sept.

Symphonic concert

May 4, 2016

2 miles west

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

Stories about motherhood

May 7, 2016

1.5 miles SW

Listen To Your Mother celebrates and validates motherhood with readings that are touching and humorous at Old South Church, Copley Square.

Mother’s Day wine/chocolate

May 7, 2016 (uncertain)

6 miles west

Mother’s Day Wine & Chocolate includes a 2-hour class, a tasting of wine and chocolate, and an Italian dinner with wine at Boston Wine School in Allston.

Steampunk festival

May 7, 2016

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.

Craft fair

May 7, 2016

23 miles north

Shop from 150 vendors at Andover Crafts in the Park.

Renaissance fair

May 7-8 and 14-15, 2016

48 miles north

NH 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.

Mother’s Day restaurants

May 8, 2016

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 8, 2016

1 mile SW

Families celebrate the Boston-based book “Make Way for Ducklings” by dressing as ducks for a Duckling Day Parade at Boston Public Garden.

Short play festival

May 8, 2016

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 & daughter art class

May 8, 2016

3.4 miles SW

Mothers and daughters can make beautiful glass beads or pendants together at Diablo Glass School.

Lilac day

May 8, 2016 (10 a.m. to 3 p.m.)

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.

Mother’s Day memorial

May 8, 2016

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 cupcakes

May 8, 2016 (12 to 2 p.m.)

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.

Mother’s Day on the farm

May 8, 2016

38 miles NW

Mom’s get free admission with a paid child at Davis Farmland, which has farm animals, children’s play areas, hayrides, and more in Sterling.

Fashion show

May 14, 2016

Location uncertain

Featuring Ambitious Models & Entrepreneurs Fashion Show (FAME) includes a shopping boutique and a runway walk at 7:45 p.m. at Boston Common Hotel.

Kite and Bike Festival

May 14, 2016

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.

Run in the mud

May 14 - 15, 2016

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.

Music festival

May 15 - 22, 2016

Cambridge locations

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

Beer festival

May 20 - 21, 2016

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.

Bluegrass festival

May 20 - 22, 2016

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.

Beverage festival

May 20 - 23, 2016

1.4 miles SW

Thirst Boston features cocktail seminars, tastings, high tea, and parties for beverage enthusiasts and industry insiders at the Fairmont Copley Plaza.

Bike parade

May 22, 2016

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.

Farm dinner

May 27, 2016 (uncertain)

10 miles west

Enjoy a specialty dinner of local farm food at Fourth Friday Farm Feasts in the Carriage House at Gore Place in Waltham for $95.

Boston Calling music festival

May 27 - 29, 2016

0.1 miles west

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

Campfire music festival

May 27 - 30, 2016

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 29, 2016

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.

Bike week

May 2016 (undated)

Greater Boston area

Find bike rodeos, rides, breakfasts, and workshops offered during Bay State Bike Week.

Irish pops

May 2016 (undated)

2.1 miles SW

A Celtic Sojourn at Pops features Boston Pops playing Celtic music, plus Irish step dancers, pipers, and vocalists at Symphony Hall.

Comedy competition

May 2016 (undated)

2.6 miles west

See 50 of Boston’s best standup comics compete in the StandUp ThrowDown tournament and vote for your favorites at ImprovBoston.

Quilt show

May 2016 (undated)

5.8 miles west

See 200 quilts that range from classic to cutting-edge at Quilters’ Connection Quilt Show, which has guided tours and demonstrations of quilting techniques at the Arsenal Center for the Arts in Watertown.

Wine and chocolate

May 2016 (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.

Get painted as you run

May 2016 (undated)

28 miles SW

Wear a white shirt, and then get bombarded by handfuls of colored cornstarch and glitter as you run the Color Run 5K at Gillette Stadium, Foxborough.

Mother’s Day talk

May 2016 (undated)

4 miles west

RSVP to hear about the nurturing nature of mothers and how we can nurture ourselves and others at Honoring Mothers: Remembering the Days of Our Childhood at Inner Space at Harvard Square. Free.

Mother’s Day tea

May 2016 (undated)

10 miles west

Take Mom to Mother’s Day Tea at Gore Place for tea and cake in a beautiful 1806 mansion in Waltham.
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© May 2016 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts.