Boston events for May 2016. 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 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.

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 family-friendly Community Day on Sunday 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 hundreds of creative experiences, artist talks, performances, behind-the-scenes tours, and kids’ activities. Many are free. Repeats in Sept.

Big top circus

May 1 - 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.

MayFair at Harvard Square

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

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.)

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.

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.

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.

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.

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.

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.

Charlie Brown musical

May 6 - 22, 2016

24 miles SW

Comic book characters Charlie Brown, Snoopy, Linus, Lucy, Sally, and Schroeder come to life in You’re a Good Man, Charlie Brown in Walpole.


May 6 - 28, 2016

0.6 miles SW

Boston Ballet presents Mirrors, four groundbreaking contemporary works at the Boston Opera House.

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.

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.

Historic home tour

May 7 - June 5, 2016 (closed Mon. & Tues.)

11.8 miles west

Walk through 20 rooms of a historic home remodeled by experts at Decorators’ Show House, and then visit exhibitors in the barn in West Newton for ages 12+. Discount tickets for Wed., Thurs., Fri. $10.

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.

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.

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.

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.

Symphonic jazz

May 18 - 19, 2016 (8 p.m.)

2.1 miles SW

Gershwin Celebration features the vibrant, lush, jazzy, and uniquely American sound of George Gershwin performed by the Boston Pops at Symphony Hall.

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.

Music concert

May 21, 2016 (10 a.m. to 5 p.m.)

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.

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.

Comedy about marriage

May 22, 2016

7.6 miles NE

You Say Tomato, I Say Shut Up features a delightfully crazy marriage in which husband and wife throw good taste and decorum out the window at Regent Theatre.

Wine on a sailboat

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

0.8 miles SE

Head to Courthouse Dock for a two-hour evening sail aboard the historic Roseway with wine and snacks on a Wine Down Wednesday Sail 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.

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.

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.

Campfire music festival

May 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.

Sailboat ride

May 30 - June 30, 2016

0.4 miles SE

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

Evening cruise

May 30 - 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. Leaves 1 Long Wharf. Discount tickets Sun. to Wed. $17.

Wine tasting

May 31, 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.

Woody Allen musical

May 31 - June 5, 2016

51 miles SW

Bullets Over Broadway tells the story of an aspiring playwright and features big song-and-dance numbers from New York’s Jazz Age in Providence, RI. Discount tickets $27.

Duckmobile tour

May 31 - June 17, 2016

1 mile NW

Ride a giant Duckmobile from the Museum of Science past city sights and then into the Charles River on the narrated and unforgettable Boston Duck Tours.

Discount tickets $27.

Solve the crime

May 31 - June 30, 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 $35.

Blue Man show

May 31 - Oct. 2, 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 $52.
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© May 2016 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts.