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.

Jazz & blues festival

September 1 - 3, 2016

83 miles SE

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

Free movies

September 1 - 23, 2016 (dusk)

Boston area

Watch family films outdoors on Mayor Walsh’s Movie Nights in Boston Common, parks, and playgrounds. Free.

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.


September 3, 2016 (8:30 p.m.)

0.3 miles east

Watch the Labor Day Weekend Fireworks launched from a barge anchored between the North End and Seaport. “Best viewing locations are East Boston’s Piers Park, downtown’s Christopher Columbus Park and Long Wharf, and the Seaport’s Fan Pier.” Free.

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.

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, battling knights, fire-eaters, 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 - 11, 2016

Cambridge locations

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

Comedy night

September 9, 2016 (5:15 p.m.)

37 miles south

Oddball Comedy & Curiosity Festival features nationally known comedians at Xfinity Center in Mansfield.

Ice skating show

September 9 - 10, 2016

4 miles west

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

Arts festival

September 10, 2016

0.3 miles east

Boston’s Arts Festival includes an 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 (12 to 6 p.m.)

7.6 miles west

The Vegetarian Food Truck & Craft Beer Festival features 15 food vendors and a dozen breweries at The Arsenal Project in Watertown.


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 12:30 p.m. 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+.

Taste of Jamaica Plain

September 15, 2016 (6 to 9 p.m.)

3.5 miles SW

Taste of Jamaica Plain features food from neighborhood restaurants, live music, and a silent auction at Franklin Park Zoo’s Tropical Forest exhibit.

Food & Wine Festival

September 15 - 18, 2016

Boston locations

The Food & Wine Festival includes a gala on Thursday; live music, sampling, and chef demos on Saturday; and two tasting events on Sunday at WGBH. (See Sept. 18 below for more about the tasting events.)

Greek festival

September 16 - 18, 2016

6.5 miles SW

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

Outdoor concert

September 17, 2016 (1:45 p.m., gates open 11 a.m.)

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.

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.

The Artisan Taste

September 17, 2016 (4 p.m., VIP 3)

5.1 miles west

The Artisan Taste features chef tastings, vintner & brewer tastings, cooking demonstrations, artisan vendors, and live country blues at WGBH Studios.

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 to the $20 New England Blues Festival [sound] at Middleboro Lodge of Elks to support charity. Food and beverage vendors.

Cannabis rally

September 17 - 18, 2016 (12 to 6 p.m.)

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.

Buy American

September 17 - 18, 2016 (10 a.m. to 6 p.m.)

1.8 miles SE

Shop from 40 vendors selling American-made goods at American Field at The Innovation and Design Building in the Seaport area. 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.

College student festival

September 17 & 24, 2016

Boston & Worcester

CollegeFest is a back-to-school event with live music, student entertainment, prizes, and giveaways at Fenway Park. 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.

Run on Spectacle Island

September 18, 2016

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.

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.

Brunch extravaganza

September 18, 2016 (11 a.m. to 2 p.m.)

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 for age 21+.

Tasting event

September 18, 2016 (4 to 6:30 p.m.)

5.1 miles west

Taste food on sticks (kebabs, corn dogs, satay, and pie pops) from 10 chefs and vote for your favorite at Food Fight, with craft beer, wine, hard cider, and cooking demos at WGBH Studios for age 21+.

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.

Film festival

September 22 - 26, 2016

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 & music festival

September 23 - 24, 2016

0.1 miles west

The Copenhagen Beer Celebration comes to Boston this year, with 50 brewers, 9 bands, and food vendors in City Hall Plaza for age 21+.

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, food vendors, 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 46 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.

Street food

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

2.5 miles SW

A ticket to Phantom Gourmet Food Festival gets you samples of 100 kinds of food near Fenway Park. Must be age 21+. Expect lines.

Marshmallow festival

September 24, 2016 (3 to 7 p.m.)

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 (11 a.m. to 3 p.m.)

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.

Waltham fall festival

September 24, 2016 (12 to 5 p.m.)

11 miles west

Fall Festival features local food and craft beer, live music on three stages, kids’ entertainment, and a pumpkin drop at Gore Place in Waltham. Children age 12 and younger are free. No pets.

Visit art studios

September 24 - 25, 2016

1.6 miles SW

Follow the map to visit studios of 200 local artists plus local galleries during South End Open Studios. Free.

Oktoberfest in Rhode Island

September 24 - 25, 2016

51 miles SW

International Oktoberfest has seasonal brews, savory German and American food, cocktails, and music in downtown Providence, RI.

Haunted house in 2 locations

September 24 - Nov. 5, 2016

50 miles

Factory of Terror includes cutting-edge special effects and actors in professional makeup in Fall River and Worcester. See schedules.

Tasting event

September 25, 2016 (12 to 4 p.m.)

0.6 miles SE

Taste of Downtown Crossing features local musicians, a wine and beer garden, cooking demonstrations, and tastes of 20 local restaurants on Avenue de Lafayette.

Street festival

September 25, 2016 (12 to 6 p.m.)

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.

Environmental films

September 28 - 29, 2016

2.4 miles NW

See four films on topics ranging from the science and impact of climate change, to water scarcity, and the dark side of technology at the Environmental Film Festival at Landmark Kendall Square in Cambridge.

Documentary films

September 28 - Oct. 2, 2016

multiple locations

GlobeDocs Film Festival is “focused on telling important stories, large and small.” Films are followed by discussions with journalists and film makers, except the short film series.

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 dozens of creative experiences, artist talks, performances, behind-the-scenes tours, and kids’ activities. Many are free. Repeats in April.

Haunted ski area

September 30 - Oct. 31, 2016

29 miles NW

Witch’s Woods has seven attractions, including a haunted hayride and nightmare mansion, at Nashoba Valley Ski Area. Open Thursday to Sunday & Oct. 31.
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© September 2016 calendar of events in Boston, MA. Best events, fairs, festivals, and things to do in Boston, Massachusetts. bos-09