Boston events, festivals, things to do – May 2018

May 2018
best events in Boston

Film festival

May 1 - 2, 2018 (begins April 25)

Boston locations

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


May 1 - 6, 2018 (begins April 27)

Greater Boston

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

Cinco de Mayo pub crawl

May 5, 2018

0 miles

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

Home tour

May 5, 2018

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.

Art walk

May 5 - 6, 2018

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 will be open until 4 p.m. Free.

Pet expo

May 5 - 6, 2018

34.5 miles NW

Bring your pet (see rules) to New England Pet Expo, which offers vendors, vaccinations, entertainment, and adoptions at Tsongas Center at UMass Lowell. Free.

Charity walk

May 6, 2018

1 mile SW

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

Short play festival

May 6, 2018 (noon to 10 p.m.)

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.

MayFair at Harvard Square

May 6, 2018

3.6 miles west

MayFair offers three stages of entertainment, chalk art, beer gardens, and vendors of food, crafts, and jewelry at Harvard Square. Rain date May 20. Free.

Comedy for a cause

May 11, 2018

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.

Adventure race

May 11 - 12, 2018

Location uncertain

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

Japanese festival

May 12, 2018

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.

Steampunk festival

May 12, 2018

12 miles west

Watch City Steampunk Festival promises 50 vendors, kids’ activities, food trucks, and costumed performers in Waltham. Free.

Renaissance fair

May 12 - 13 and 19 - 20, 2018

54 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 Fremont, NH.

Mother’s Day restaurants

May 13, 2018

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 13, 2018

0.4 miles east

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

Duckling parade

May 13, 2018

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.

Lilac day

May 13, 2018

5.4 miles SW

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

Mother’s Day memorial

May 13, 2018

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 13, 2018

10 miles west

Take Mom to Mother’s Day Tea at Gore Place to have tea and cake and then tour the beautiful 1806 mansion at Gore Place in Waltham.

Mother’s Day comedy

May 13, 2018

14 miles SW

The Boston Comedy Chicks tell jokes about motherhood at their Mother’s Day Comedy Show at the Holiday Inn in Dedham (plus Manchester).

The King and I

May 15 - 20, 2018

47 miles west

The King and I is a “breathtaking and exquisite” [NY Times] musical by Rodgers & Hammerstein set in 19th-century Bangkok, winning Best Musical Revival, at The Hanover Theatre for the Performing Arts.

Discount tickets $51 to $81.

Nantucket Wine Festival

May 16 - 20, 2018

112 miles SE via ferry

Nantucket Wine Festival offers 70 events, including tastings, seminars, meals, and marketplaces.

Kite and Bike Festival

May 19, 2018

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 19, 2018

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.

Lamb tasting

May 20, 2018 (3 p.m., VIP 2 p.m.)

1.3 miles NW

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 Royal Sonesta Cambridge for age 21+.

Memorial Day Parade

May 20, 2018

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 and then Holland Street. Free.

Boston Calling music festival

May 25 - 27, 2018

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 25 - 28, 2018

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.

Bike week

May 2018 (undated)

Greater Boston area

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

Return of the Swans

May 2018 (undated)

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, children’s activities, and a welcome by the mayor. Free.

Beer festival

May 2018 (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.

New song competition

May 2018 (undated)

2 miles west

Writers pitch their songs to 12 vocalists, who perform with a band before a panel of judges to win prizes at Perfect Pitch Concert at Berklee Performance Center.

Music and food benefit

May 2018 (undated)

2.4 miles west

Sample fare from 15 Boston restaurants, dance to reggae, and attend an auction at Beyond Shelter at House of Blues for the Friends of Boston’s Homeless.

Comedy competition

May 2018 (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 2018 (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, plus a party in the park. Free.

Dessert night

May 2018 (undated)

5 miles SW

Sweet Tastes of JP (Jamaica Plain) features an assortment of desserts from Boston bakeries, a no-host bar, and music at Bella Luna & The Milky Way to support seniors.

Bicycle film festival

May 2018 (undated)

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. Films repeat June 15 in Northampton and June 16 in Danbury, CT.

Art walk

May 2018 (undated)

1.1 miles SE

See galleries and artists’ studios in historic waterfront warehouses during Spring Art Walk in Fort Point. Free. Repeats in Oct.

Mother’s Day cupcakes

May 2018 (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, $75 includes adult & child.