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

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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.

Free movies

September 1 - 23, 2016 (dusk, starts Aug. 8)

Boston area

Watch family films outdoors on Mayor Walsh’s Movie Nights (see their page 5) in Boston Common, parks, and playgrounds. Free.

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.

Newburyport music festival

September 3, 2016 (noon to dusk)

37 miles NE

Newburyport’s Riverfront Music Festival has music, food vendors, and a beer tent at Waterfront Park in Newburyport. Free.

Brunch cruise

September 3 - 25, 2016 (weekends)

0.3 miles east

Eat brunch as you cruise past historic lighthouses of Boston Harbor on the narrated Lighthouse Brunch Cruise.

Discount tickets $45.

Medieval fair

Sept. 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.

Evening cruise

September 4 - 18, 2016 (from June)

0.3 miles east

View the city’s skyline and harbor on a Sunset Cruise, and watch as the USS Constitution fires her cannon and lowers her flag to end the day, departing from 1 Long Wharf. Discount tickets Sun. to Wed. $17.

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 - 11, 2016

Cambridge locations

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

Arts festival

September 10, 2016 (rain date Sept. 11)

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.

Game festival

September 10, 2016

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.

Jamaica Plain music festival

September 10, 2016 (12 to 7 p.m.)

4.6 miles SW

JP Music Festival has two stages of music by 20 local artists and bands, plus food trucks and children’s activities northeast of Jamaica Pond. Free.

Vegan food trucks

September 10, 2016

7.6 miles west

Bring blankets or lawn chairs to the Vegan Food Truck Festival at The Arsenal Project in Watertown to enjoy food made without any animal or dairy products.


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.

Wine on a sailboat

September 14, 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+.

Sailing with drinks

September 15, 2016 (5:30 p.m.)

0.8 miles SE

Head to Courthouse Dock for a two-hour evening sail aboard the historic Roseway while enjoying local beer, wine, and more on a Thirsty Thursday Sail for age 21+.

Food & Wine Festival

September 15 - 18, 2016

Boston locations

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

Street festival

September 17, 2016

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.

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+.

Small-town blues festival

September 17, 2016

41 miles south

Bring a lawn chair and $20 to the New England Blues Festival [sound] at Middleboro Lodge of Elks, which supports charity and veterans.

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 Hub on Wheels bike ride, which is 10 or 40 miles.

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, and food-inspired arts and crafts at Rose Kennedy Greenway. Free.

Welcome autumn

September 18, 2016 (5 to 7:30 p.m.)

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.

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.

Brunch extravaganza

September 18, 2016

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.

Wine & food festival

September 22 - 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 in Newport, RI.

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.

Fashion week

September 23 - 30, 2016

Boston locations

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

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.

Street food

September 24, 2016 (12 to 4 p.m.)

2.5 miles SW

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

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 the 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.

Street festival

September 25, 2016

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.

Taste of Winthrop

September 28, 2016 (6 to 9 p.m.)

6.7 miles NE

Taste food from 30 local restaurants, caterers, cafes, and bakeries at Taste of Winthrop, with views and entertainment at the Winthrop Yacht Club.

Oktoberfest - Boston

September 30 - Oct. 1, 2016

1.5 miles SE

Harpoon Octoberfest features beer, bratwurst, waltzing musicians in lederhosen, and contests at Harpoon Brewery. Cash cover charge and age 21 ID.


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.

Haunted ski area

September 30 - Oct. 31, 2016

29 miles NW

Witch’s Woods [sound] has 6 attractions, including a haunted hayride and nightmare mansion, at Nashoba Valley Ski Area. Open Thursday to Sunday.


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.

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 in May.

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.

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.

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.

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.

Ice skating show

September 2016 (undated)

4 miles west

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

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.

Greek festival

September 2016 (undated)

6.5 miles SW

Taste Greek food and pastries, dance to live music, and watch folk dancing at the GreekFest Boston in Brookline. Free.

Waltham fall festival

September 2016 (undated)

11 miles west

Fall Festival features a giant pumpkin drop, live music, a beer tent, food & craft vendors, quilts, classic cars, lawn games, and wagon rides at Gore Place in Waltham. Kids 12 and under free.

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.

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.
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© September 2016 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts.