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.

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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 10-mile Walk for Hunger and 5K run, which begin on Boston Common.

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.

Arts festival

May 1, 2016 (begins April 28)

3.5 miles NW

Arts First celebrates student and faculty creativity with more than 100 music, theater, dance, film, and visual arts events at Harvard University. Most are free.

Visit art studios

May 1, 2016 (begins April 30)

4.2 miles SW

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

Cinco de Mayo Festival

May 1, 2016 (3 to 7 p.m.)

5.5 miles NE

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

Jazz festival

May 1, 2016 (begins April 29)

7.6 miles NE

A-Town Jazz Festival has concerts on three days, with the main event Sunday evening at Regent Theatre in Arlington.

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.

MayFair at Harvard Square

May 1, 2016 (12 to 6 p.m.)

3.6 miles west

MayFair offers three 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.)

Flowers & art

May 2, 2016

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 2 - 4, 2016

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 2 - 8, 2016

Greater Boston

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

Variety show

May 3, 2016 (7:15 p.m.)

4.3 miles NW

The Teaseday Club presents an evening of song, dance, burlesque, magic, comedy, music, and juggling at Davis Square Theatre. Discount tickets $11.

Romantic play

May 3 - 15, 2016

3.4 miles west

Arcadia is a series of love stories set on an English country estate, exploring the nature of truth and time as it switches between 1809 and today, at Central Square Theater in Cambridge. Discount tickets $23.

Solve the crime

May 3 - 31, 2016

1 mile SW

The award-winning comedy Shear Madness is a whodunit with audience participation, set in a hair salon at Charles Playhouse. Discount tickets $25.

Symphonic concert

May 4, 2016 (8 p.m.)

2 miles west

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

Big top circus

May 4 - 8, 2016

0.1 miles west

The Grand Tour by Big Apple Circus has a 1920s travel theme with acrobats, aerialists, jugglers, clowns, rescue animals, and a band in a tent at City Hall Plaza. Discount tickets $10 to $40.

Funny, romantic operetta

May 4 - 8, 2016

0.9 miles SW

Shubert Theatre takes on an lush look for The Merry Widow, the story of a rich widow and the men who court her. Discount tickets $20 to $90.

Blue Man show

May 4 - June 26, 2016

1 mile SW

Blue Man Group puts on an exciting show that combines comedy, theater, music, and special effects at Charles Playhouse. Discount tickets $65.

Cinco de Mayo pub crawl

May 5, 2016 (4 p.m.)

0 miles

Cinco de Mayo Pub Crawl Boston includes drink specials at the Hard Rock Cafe and Mija Cantina at Faneuil Hall. Discount tickets $2.50.

Cinco de Mayo at WGBH

May 5, 2016 (7 to 9 p.m.)

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. Discount tickets $20.

Witty comedy about manners

May 5 - 8, 2016

1.6 miles NW

Written in 1777, The School for Scandal is a timeless and scathing portrait of British high society that’s full of witty dialogue, mistaken identities, and intrigue over infidelity at Cambridge Multicultural Arts Center. Discount tickets $20.

Classic mystery theater

May 5 - 22, 2016

9.2 miles north

Based on the classic film noir, Laura is a play that follows a NYPD detective obsessed with solving the murder of a mysterious woman at Stoneham Theatre. Discount tickets $25.

Country music

May 6, 2016 (8 p.m.)

0.9 miles SW

Nashville in Concert features stars of the ABC TV show “Nashville” at Citi Performing Arts Center. Discount tickets $48.

Wine and chocolate

May 6, 2016 (7 to 10 p.m.)

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.

Sex farce

May 6 - 7, 2016

3.7 miles NE

An Egyptian couple invites an American into their bedroom in Threesome, with hilariously awkward results that soon give way to secrets and tensions at Chelsea Theatre Works. Discount tickets May 7, $10.

Golden Girls in drag

May 6 - 15, 2016

1.3 miles SW

Watch a “lost” reunion episode of popular TV sitcom The Golden Girls, live onstage with an all-male cast at Club Cafe. Discount tickets $15.

Family musical

May 6 - 15, 2016

3.7 miles SW

A Year with Frog and Toad is about the enduring friendship between dissimilar pals (a cheerful frog and a grumpy toad) at Wheelock Family Theatre. Discount tickets $16.

Witty & romantic musical

May 6 - 22, 2016

9.3 miles NW

A Tony Award winning play by Sondheim, A Little Night Music follows the romantic lives of several couples over a weekend at a Swedish country house in 1900, in Winchester. Discount tickets $21.


May 6 - 28, 2016

0.6 miles SW

Boston Ballet presents Mirrors, four groundbreaking contemporary works at the Boston Opera House. Discount tickets $45.

Mother’s Day wine/chocolate

May 7, 2016 (4:30 to 7:30 p.m.)

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 7, 2016 (2 p.m.)

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.

Steampunk festival

May 7, 2016 (gala May 6)

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.

Home tour

May 7, 2016 (11 a.m. to 3 p.m.)

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.

Craft fair

May 7, 2016

23 miles north

Shop from 150 vendors at Andover Crafts in the Park.

Dinner cruise

May 7 - 8, 2016

multiple locations

Enjoy dinner, a DJ dance, and three hours of views onboard the Odyssey. Discount tickets $91.

Renaissance fair

May 7-8 and 14-15, 2016

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.

Odd romantic musical

May 7 - June 4, 2016

2 miles SW

Three Marines deploying for Vietnam bet who can get the ugliest date in Dogfight, a rousing song and dance adventure about unexpected love, loss, and brotherhood at Calderwood Pavilion. Discount tickets $30.

Evening cruise

May 7 - Sept. 18, 2016

0.3 miles east

View the city’s skyline and inner harbor on a Sunset Cruise, and watch as the USS Constitution fires her cannon and lowers her flag to end the day. Departs from 1 Long Wharf. Discount tickets $17 (Sunday to Wednesday).

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.

Mother’s Day cruise

May 8, 2016 (noon)

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 8, 2016

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.

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’s Day comedy

May 8, 2016 (3 & 7 p.m.)

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. Discount tickets $18.

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 tea

May 8, 2016 (3 p.m.)

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 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.

Boston Pops - classic rock

May 10, 2016 (8 p.m.)

2.1 miles SW

Classic Rock From the Beatles to Led Zeppelin features Tom Scholz of the band “Boston” plus the Boston Pops at Boston Symphony Hall. Discount tickets $25 to $60 (May 11).

Irish Riverdance

May 10 - 15, 2016

0.9 miles SW

Riverdance is an exhilarating celebration of Irish music, song, and dance at Citi Performing Arts Center.

Sailboat ride

May 11 - June 30, 2016

0.4 miles SE

Tour Boston Harbor aboard beautiful pilot schooner Adirondack III, which sails from Rowes Wharf.

Kite and Bike Festival

May 14, 2016 (11 a.m. to 4 p.m.)

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.

British rock legends

May 14, 2016 (8 p.m.)

18 miles NE

Kim Simmonds and Savoy Brown perform at Larcom Theatre in Beverly.

Discount tickets $15.

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.

Bike week

May 14 - 22, 2016

Greater Boston area

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

Music festival

May 15 - 22, 2016

Cambridge locations

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

Nantucket Wine Festival

May 18 - 22, 2016

112 miles SE via ferry

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

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

multiple locations

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

Fresh Peter Pan

May 20 - June 26, 2016

1.4 miles SW

Peter and the Starcatcher is a swashbuckling prequel to Peter Pan, a madcap adventure with music, pirates, orphans, and secret agents, at Lyric Stage Company of Boston for age 10+. Discount tickets $27.

Wine tasting

May 21, 2016 (6 to 8:30 p.m.)

0.5 miles SE

Taste Portuguese wine, ranging from the dry reds of Bairrada to the slightly effervescent whites of Vinho Verde, with appetizers at Wines of Portugal Producer Showcase at Boston Harbor Hotel.

Brunch boat tour

May 21 - Sept. 25, 2016 (weekends)

0.3 miles east

See the historic lighthouses of Boston Harbor as you eat brunch on the narrated Weekend Lighthouse Brunch Cruise.

Discount tickets $45.

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.

Beer & oyster cruise

May 22 - Oct. 30, 2016 (Sundays)

1.5 miles north

Eat fresh oysters and taste craft beer as you enjoy harbor views aboard a 1948 vintage motor yacht at Oysters and Craft Brews Cruise departing from Charlestown Navy Yard.

Discount tickets $54.

Tequila & taco cruise

May 24 - Oct. 25, 2016

1 mile SE

Tequila & Taco Tuesday Cruise has views of Boston Harbor and the the USS Constitution, a free taco bar, and a cash bar aboard a 1948 vintage motor yacht departing from Fan Pier Marina. Discount tickets $39.

Wine on a sailboat

May 25, 2016 (5:30 p.m.)

0.8 miles SE

Head to Courthouse Docks for a two-hour evening sail aboard the historic Roseway with wine and snacks during Wine Down Wednesdays for age 21+.

Boston Pops - show tunes

May 26, 2016 (8 p.m.)

2.1 miles SW

Tony winner Sutton Foster sings Broadway theater songs accompanied by the Boston Pops at Boston Symphony Hall. Discount tickets $26 to $77.

Adventure race

May 27, 2016

0.3 miles east

Questival is a 24-hour adventure where your team completes challenges via smartphone app to win an exotic trip, at Christopher Columbus Park.

Comedy competition

May 27, 2016 (10 p.m.)

2.6 miles west

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

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 in 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.

Chocolate tour

May 28, 2016 (10:15 a.m.)

1.4 miles SW

Your reward for taking the 1-mile Back Bay Chocolate Walking Tour is chocolate samples in various shops and a scenic tour. Discount tickets $24 (2 left).
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© May 2016 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts.