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

Best events for 12 months
Best events for 12 months
September 2016
September 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 & blues festival

September 2 - 3, 2016

83 miles SE

Martha’s Vineyard Jazz & Blues Summerfest is a family friendly event on Labor Day weekend.

Sailing festival

September 2 - 4, 2016

35 miles NE

Gloucester Schooner Festival has a concert, fireworks, lobster bake, walking tour, and spectacular Parade of Sail Sunday morning before the Mayor’s Race.

Campfire music festival

September 2 - 5, 2016

3.6 miles NW

Hear new performers and watch songwriters interact and swap tunes as they sing in the round Labor Day weekend at Campfire Festival at Club Passim.

Country fair

September 2 - 5, 2016

64 miles west

The Spencer Fair is a traditional country fair with horse and tractor pulls, rabbit and poultry shows, pig races, hall exhibits, a carnival midway, live music and a demolition derby at Spencer Fairgrounds.

Medieval fair

September 3 - Oct. 23, 2016 (weekends)

49 miles south

King Richard’s Faire offers medieval food, games, and artisan shops, plus costumed acrobats, fire-eaters, battling knights, jugglers, dancers, and puppeteers in a forest near Carver. Includes Mondays for Labor Day and Columbus Day.

Labor Day festival

September 5, 2016

28 miles north

The Bread & Roses Heritage Festival presents music, theatre, dance, and storytelling on three stages, and it has vendors of food, arts & crafts, and merchandise in downtown Lawrence. Free.

Comedy festival

September 7 - 12, 2016

Cambridge locations

Boston Comedy Arts Festival fills three stages with improv, sketch, and stand-up comedy in Cambridge.


September 10 - 11, 2016

25 miles SW

Celebrate Oktoberfest with live music and dancing, kids’ games, German food, beer, wine, and crafts in a covered pavilion at the German club in Walpole.

Mountain music festival

September 10 - 11, 2016 (12 to 6 p.m.)

50 miles west

MusicFest at Wachusett Mountain features country music and running events on Saturday, and rock music and a car show on Sunday, with a weekend barbecue, beer, and local craft vendors.

Corn maze

September 10 - Oct. 31, 2016

22 miles north

A ticket to Connors Farm Corn Maze also includes hayrides, pedal carts, and activities in Danvers.

Cambridge carnival

September 11, 2016

1.8 miles west

Cambridge Carnival International features a parade of revelers in colorful handmade costumes dancing to a steel band, a stage for world music and local bands, a kids’ fest, international foods, and craft vendors. Free.

Food & Wine Festival

September 15 - 18, 2016

Boston locations

The Food & Wine Festival includes a Thursday gala; Friday dinner at Journeyman Restaurant; and weekend chef demos, chef discussion, tastings, and live music at WGBH.

Beer at the zoo

September 17, 2016 (5 to 7:30 p.m.)

8.2 miles north

Taste 20 local brewery beers with wine and sangria, and stroll among animal exhibits during Ales & Tails at Stone Zoo for age 21+.

Cannabis rally

September 17 - 18, 2016 (uncertain)

1 mile SW

Boston Freedom Rally educates the public about marijuana, promotes cultural and political change, showcases new bands, and creates a marketplace for food and crafts at Boston Common. Free.

Pet expo

September 17 - 18, 2016

16 miles north

Bring your pet (see rules) to New England Pet Expo, which offers vendors, vaccinations, entertainment, and adoptions at Aleppo Shriners Auditorium in Wilmington. Free.

Bike ride

September 18, 2016

0.1 miles west

Ride through historic neighborhoods and see views of Boston Harbor when Storrow Drive is car-free during the 10, 30, or 50 mile Hub on Wheels bike ride.

Food festival

September 18, 2016

0.4 miles NW

Boston Local Food Festival has $6 servings of locally grown and sustainably produced food, local music, chef demos, exhibitions and workshops, food-inspired arts and crafts at Rose Kennedy Greenway. Free.

Folk Music Festival

September 18, 2016

4 miles west

The Folk Music Festival is an afternoon concert of energetic music on Palmer Street in Cambridge. Free.

Home show

September 23 - 25, 2016

16 miles north

See home improvement products, services, and demos at Suburban Boston Fall Home Show at Shriners Auditorium in Wilmington. Repeats in Jan.

Scallop festival

September 23 - 25, 2016

69 miles SE

The Scallop Fest offers scallop or herb-roasted chicken dinners, music, arts & crafts, and a carnival at Cape Cod Fairgrounds in East Falmouth.

Wine & food festival

September 23 - 25, 2016

74 miles south

Taste wine on the lawn of Marble House, see seminars and celebrity chef demos, and dine at Rosecliff during Newport Mansions Wine & Food Festival, Newport, RI.

Free museum day

September 24, 2016


Get a free ticket for two people to visit one of 53 Massachusetts museums on Museum Day Live.

Berklee jazz festival

September 24, 2016

2 miles SW

Berklee BeanTown Jazz Festival offers three stages of live music, arts, crafts, a family park, and even an instrument petting zoo on Columbus Ave. between Massachusetts Ave. and Burke St. Free.

Student festival

September 24, 2016

2 miles SW

CollegeFest is a back-to-school event with local and nationally known musicians, student entertainment, prizes, and giveaways at Fenway Park. Free.

Marshmallow festival

September 24, 2016

2.8 miles NW

What the Fluff? is all about marshmallow cream, with games like Sticky Musical Chairs and Fluff Jousting, plus cooking and eating competitions, a kids’ area, and live music at Union Square in Somerville. It all honors invention of Fluff at the square in 1917. Free.

Scandinavian food

September 24, 2016

10 miles west

Enjoy authentic food, music, and crafts from Norway, Denmark, Sweden, Finland and Iceland, and see a Viking battle reenactment, at Smörgåsbord Nordic Food Festival in West Newton.

Blacksmith festival

September 24, 2016

47 miles NW

Blacksmith Art & Music Festival celebrates the art of blacksmithing with family art activities, music, arts and crafts, and food vendors in Fitchburg.

Welcome autumn

September 25, 2016

3.5 miles west

Wave goodbye to summer and celebrate the first day of fall with pre-show entertainment, a procession to the Charles River, and a sing along at RiverSing. Free.


September 30 - Oct. 9, 2016

Greater Boston

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


September 2016 (undated)

0 miles

A marathon has 26 miles, but a Beerathon has 26 Boston bars to visit with music. Check in from 12 to 3 p.m. at one of four locations.

Fashion week

September 2016 (undated)

Boston locations

Boston Fashion Week showcases the work of local fashion designers with runway shows, exhibits, panels, receptions, and networking parties.

Free movies

September 2016 (undated)

Boston locations

Watch free Summer movies outdoors. Free.

Music festival

September 2016 (undated)

0.1 miles west

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

Arts festival

September 2016 (undated)

0.3 miles east

Boston’s Arts Festival includes a covered artists’ village, two stages of performing arts, and family activities at Christopher Columbus Waterfront Park. Free.

Film festival

September 2016 (undated)

1 mile SW

Boston Film Festival (BFF) is dedicated to supporting evolving filmmakers by screening their films, holding post-screening Q & A sessions with directors, and presenting awards at Stuart Street Playhouse.

Outdoor concert

September 2016 (undated)

1.2 miles west

MixFest is a popular concert with an all-star line-up of artists at Hatch Memorial Shell on the Charles River. Free.

Run on Spectacle Island

September 2016 (undated)

Seaport is 1.5 miles SE

The Island Run is a 5K or 5 mile run on the trails of Spectacle Island for age 21+, followed by a lunch and awards as you cruise back through Boston Harbor.

Game festival

September 2016 (undated)

2.2 miles west

Play video games, tabletop games, and role-playing games at Boston Festival of Indie Games, which also hosts films and lectures for game developers and game jams for making your own games at MIT. Free.

Street festival

September 2016 (undated)

2.2 miles SE

South Boston Street Festival features live music and dance on two stages, 100 artists and local merchants, fair food, and children’s activities on East Broadway between I and L Streets. Free.

Street food

September 2016 (undated)

2.5 miles SW

Sample 60 kinds of food at the Phantom Gourmet Food Festival near Fenway Park. Age 21+ with ID.

Family beach party

September 2016 (undated)

2.7 miles SE

Celebrate summer’s end at the End of Summer Beach Party with live music, food, games, and swimming at Curley Community Center in South Boston. Free.

Greek festival

September 2016 (undated)

2.8 miles SW

Taste Greek food and pastries, dance to live music, and watch folk dancing at the GreekFest Boston at Greek Orthodox Cathedral of New England. Free.

Vegan food trucks

September 2016 (undated)

3.5 miles west

Bring blankets or lawn chairs to the Vegan Food Truck Festival at Central Square in Cambridge to enjoy food made without any animal or dairy products.

Ice skating show

September 2016 (undated)

4 miles west

An Evening with Champions features world-class skaters at the Bright Hockey Center in Allston.

Street festival

September 2016 (undated)

4.1 miles west

Allston Village Street Fair offers activities for families, two stages of live bands, street performers, an artist and vendor market, international food, and an amusement area on Harvard Avenue in Allston. Free.

Jamaica Plain music festival

September 2016 (undated)

4.6 miles SW

JP Music Festival has two stages of music by 21 local artists and bands, plus food trucks and children’s activities north of Jamaica Pond. Free.

Brunch extravaganza

September 2016 (undated)

5.1 miles west

Brunch Bar offers 50 tasting stations with brunch dishes and morning cocktails, plus chef demos, and live music at WGBH Studios.

Country fair in the city

September 2016 (undated)

5.8 miles SW

Make cheese, press cider, and learn how to pickle, raise bees, grow mushrooms, and make flour at the Urban Agriculture Fair at Loring Greenough House in Jamaica Plain. Free.

Oktoberfest in Mendon

September 2016 (undated)

43 miles SW

Enjoy German beer, food, music, and polka dancing at the family-friendly OktoberPhest at Mendon Drive-In.

Beer festival

September 2016 (undated)

1.1 miles SE

Kick off Labor Day weekend with 100 beers from state brewers guild members at the indoor-and-outdoor Mass Brewers Fest at 200 Seaport Boulevard.

Dog festival

September 2016 (undated)

22 miles NE

Pooch-A-Palooza is an outdoor dog and music festival with dog performances, contests, vendors, groomers, photos, kids’ activities, and food trucks in Topsfield.

Newburyport music festival

September 2016 (undated)

37 miles NE

Newburyport’s Riverfront Music Festival has music, food vendors, and a beer tent at Waterfront Park in Newburyport. Free.
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© September 2016 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts.