Boston events September 2019. Things to do in Boston.

Best events for 12 months

Boston events September 2019

Late night cruise

September 1, 2019
(boarding 10:10 p.m.)
1.1 miles SE
Wear white for the Pier Pressure cruise Labor Day weekend with three hours of views and DJs (Big O and Sensation) playing open format and house music on the Spirit of Boston, leaving 200 Seaport Boulevard.

Ticket deal $20

Country fair

September 1, 2019
(begins Aug. 30)
64 miles west
The Spencer Fair is a traditional country fair with horse and tractor pulls, farm exhibits, farm animals (cattle, chickens, rabbits), giant pumpkins, a carnival midway, live music, and a demolition derby at Spencer Fairgrounds.

Campfire music festival

September 1 - 2, 2019
(begins Aug. 30)
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. Repeats in May.

Sailing festival

September 1 - 2, 2019
(begins Aug. 30)
35 miles NE
Gloucester Schooner Festival begins with a block party on Friday evening. Saturday includes Gloucester Maritime Heritage Day, a concert, a boat parade of lights (7 p.m.), and fireworks (9:15 p.m.). The Parade of Sail is Sunday morning before the Mayor’s Race.

Dogs on boats

September 1 & 21, 2019
(boarding 1:30 p.m.)
0.5 miles SE
Each adult can bring one dog aboard the Dog Days of Summer Cruise for two hours of fresh breezes and harbor views, departing from 60 Rowes Wharf.

Ticket deal $6 to $16

Evening harbor cruise

September 1 - Oct. 12, 2019
0.5 miles SE
Take a 90-minute Sunset Cruise of Boston Harbor with skyline views, departing from 60 Rowes Wharf.

Ticket deal $13

Medieval fair

September 1 - Oct. 20, 2019
(begins Aug. 31)
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. Open weekends plus Sept. 2 and Oct. 14 in 2019.

Ticket deal 2 for $49 (September)

Labor Day festival

September 2, 2019
28 miles north
The Bread & Roses Heritage Festival presents music, theater, dance, and puppets on three stages, and it has vendors of food, arts & crafts, and merchandise in downtown Lawrence. Free.

Free movies in parks

September 6, 2019
(begins Aug. 5)
Boston area
Watch family films outdoors on Mayor Walsh’s Movie Nights [page 5] in neighborhood parks. Free.

Family puppet show

September 6, 2019
(6 p.m.)
46.7 miles west
Peppa Pig Live is an action-packed show featuring your favorite characters from TV’s “Nick Jr.” as life-size puppets and costume characters in an all singing, all-dancing adventure at The Hanover Theatre for the Performing Arts in Worcester.

Ticket deal $18 to $30

Boston Night Market

September 7, 2019
(4 to 10 p.m.)
0.1 miles west
Shop for food and merchandise, visit the beer garden, and play games at the Boston Night Market in City Hall Plaza. Children age six and younger are free.

Jamaica Plain music festival

September 7, 2019
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.

Blues and Brews

September 7, 2019
(1 p.m.)
31 miles NW
A ticket to Blues N Brews gets you five beer samples from a dozen craft breweries, food for sale, and blues bands in Lowell. Children age 13 and younger are free.

Arts festival

September 7 - 8, 2019
0.3 miles east
The Boston Arts Festival features 70 local visual artists and craft makers, plus musicians performing onstage at Christopher Columbus Waterfront Park. Free.


September 7 - 8, 2019
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.

Halloween on the farm

September 7 - Nov. 3, 2019
22 miles north
A ticket to Connors Farm Corn Maze also includes hayrides, pedal carts, and activities in Danvers. The flashlight maze and haunted farm are only open Friday and Saturday nights, plus a few extra days.

Chocolate tour

September 7 - Dec. 14, 2019
(Saturdays 12:30 p.m.)
2.1 miles SW
Take a two-hour walk learning about the history of chocolate-making, with four stops for champagne truffles, chocolate confections, and even a chocolate cocktail on the Tipsy Chocolate Back Bay Walking Tour for age 21+.

Ticket deal $48

Cambridge carnival

September 8, 2019
1.8 miles west
Cambridge Carnival 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.

Small-town blues festival

September 8, 2019
(12 to 6 p.m.)
41 miles south
Bring a lawn chair to the $20 New England Blues Festival [website has sound on some devices] at Middleboro Lodge of Elks to support charity. Food and beverage vendors.

The Who

September 13, 2019
(8 p.m.)
2.5 miles SW
The Who plays an epic set of what Pete Townshend calls “all the hits, picks, mixes, and misses” of the band’s career at Fenway Park.

Ticket deal $60 to $85

Free fitness festival

September 14, 2019
0.1 miles west
Boston Social Fitness Festival promises “fun activities for all ages and fitness levels” at Boston City Hall Plaza. Free.

Street festival

September 14, 2019
(11 a.m. to 4 p.m.)
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 (from I to L Street). Free.

Game festival

September 14, 2019
6.1 miles west
Play digital games, tabletop games, and role-playing games at Boston Festival of Indie Games (BostonFIG Fest), which also has an artists’ alley and a scavenger hunt at Harvard Athletic Complex. Free.

Beer at the zoo

September 14, 2019
(5 to 7:30 p.m.)
8.2 miles north
Taste beer from 20 breweries with food samples, and stroll among animal exhibits during Ales & Tails at Stone Zoo for age 21+.

Bicycle ride

September 15, 2019
0.1 miles west
Ride through historic neighborhoods and see views of the Charles River from car-free Storrow Drive (plus Boston Harbor on the longer route) during the Hub on Wheels bike ride, with a choice of 12 or 40 miles.

Food festival

September 15, 2019
0.4 miles NW
Boston Local Food Festival serves locally grown and sustainably produced food, local music, chef demos, educational exhibits, vendors, and a family zone at Rose Kennedy Greenway. Free.

Free harbor cruise

September 16, 2019
(also Aug.)
1.3 miles SE
Sign up for a Free Share the Harbor Cruise to Boston Lighthouse or Spectacle Island aboard Provincetown II, featuring environmental education and songs and stories of the sea, departing from the dock at the World Trade Center in Seaport.

Film festival

September 19 - 22, 2019
multiple locations
Boston Film Festival (BFF) is dedicated to supporting evolving filmmakers by screening their new films. Directors attend Q & A sessions after some films.

Gourmet wine & food festival

September 19 - 22, 2019
74 miles south
Taste wine on the lawn of Marble House, attend seminars and celebrity chef demonstrations, and enjoy wine dinners during Newport Mansions Wine & Food Festival in Newport, RI for age 21+.

Greek festival

September 20 - 22, 2019
6.5 miles SW
Taste Greek food and pastries, dance to live music, and watch folk dancing at the GreekFest Boston in Brookline. Free.

Free museum day

September 21, 2019
Get a free ticket that allows two people to visit one of the many museums participating in Museum Day Live.

Cannabis rally

September 21, 2019
(12 to 8 p.m.)
1 mile SW
Boston Freedom Rally celebrates legal marijuana in Massachusetts with inspirational speakers, two stages of live music, and vendors at Boston Common. Free.

Run on Spectacle Island

September 21, 2019
Seaport is 1.5 miles SE
The Island Run is a 5K or 5-mile run on the trails of Spectacle Island, followed by a lunch and awards as you cruise back through Boston Harbor.

College student festival

September 21, 2019
2.5 miles SW
CollegeFest is a back-to-school event with live music, student entertainment, prizes, and giveaways at Fenway Park. Free.

Street food

September 21, 2019
(noon to 4 p.m.)
2.5 miles SW
A ticket to Phantom Gourmet Food Festival gets you samples of 100 kinds of food, with beverages for sale near Fenway Park. Must be age 21+. Expect lines.

Marshmallow festival

September 21, 2019
2.8 miles NW
What the Fluff? celebrates marshmallow cream with games (Sticky Musical Chairs and Fluff Jousting), cooking and eating competitions, a kids’ area, and live music at Union Square in Somerville, where Fluff was invented in 1917. Rain date is Sept. 22, 2019. Free.

Welcome autumn

September 21, 2019
3.5 miles west
Say goodbye to summer and celebrate the first day of fall with a folk band, a puppet parade from Harvard Square to the Charles River, and a sing along at Revels RiverSing. Free.

Beer festival

September 21, 2019
(1 to 5 p.m.)
46.6 miles west
The Great Mass Collab [formerly Mass Fermentational] offers unlimited samples from 50 breweries with food trucks outdoors in Worcester Common for age 21+. No pets.

Beer festival

September 21, 2019
67 miles SE
Sample 250 beers from 75 breweries at Cape Cod Brew Fest at the Cape Cod Fairgrounds in East Falmouth for age 21+.

Visit art studios

September 21 - 22, 2019
1.6 miles SW
Follow the map to visit studios of 200 local artists plus local galleries during South End Open Studios. Free.

Mind-reading comedy

September 21 - Oct. 27, 2019
0.4 miles SW
Master mentalist Jon Stetson entertains with a funny show that “blends the art of mystery with the study of psychology, the predictability of human nature, and the power of intuition” at Omni Parker House.

Ticket deal $20 to $50

Fashion week

September 22 - 28, 2019
Boston locations
Boston Fashion Week showcases the work of local fashion designers with runway shows, exhibits, panels, receptions, and networking parties.

Cirque show

September 25 - Oct. 13, 2019
0.8 miles SW
With a theme of people in transit, Passengers features awe-inspiring acrobatic feats, avant-garde dance, and comedy by the innovative performers of “7 Fingers” from Montreal at Cutler Majestic Theatre.

Ticket deal $35

Free country music

September 26, 2019
(7 to 9 p.m.)
0.2 miles west
Country in the City invites a country music legend to perform a concert in City Hall Plaza. Free.

Glow party

September 26, 2019
(doors 7 p.m., show 8 p.m.)
2.4 miles SW
Glow Boston Fall Fest promises Boston’s best DJs and biggest dance floor, glow-body painting, UV black lights, art installations, and interactive performers at the House of Blues for age 18+.

Ticket deal $9 to $15

Tap-dancing musical

September 27 - Oct. 20, 2019
20 miles NW
42nd Street is an upbeat musical with popular songs about a chorus girl working hard to make it on Broadway, at Umbrella Center for the Arts in Concord.

Ticket deal $18 to $22

Interactive Sleepy Hollow

September 27 - Nov. 3, 2019
59 miles east
Dress warmly and head to Old Sturbridge Village for The Sleepy Hollow Experience, a ghoulish guided walk through the countryside featuring encounters with characters like the Headless Horseman. Food is sold before the show and during intermission.

Chinatown festival

September 28, 2019
(1 to 4 p.m.)
0.9 miles south
Experience Chinatown Arts Festival promises music and dance performances, family-friendly workshops, and pop-up events in Boston Chinatown. Free.

Food festival

September 28, 2019
3.5 miles NW
Let’s Talk About Food has cooking demonstrations, food talks and panels, samples, local chefs, and nutritionists in Cambridge.

Blacksmith festival

September 28, 2019
47 miles NW
Fitchburg Forge-in celebrates the art of blacksmithing with competitions, demonstrations, family art activities, music, arts and crafts, and food vendors at Riverfront Park in Fitchburg.

Buy American

September 28 - 29, 2019
2.4 miles SE
Shop from vendors selling American-made goods at the American Field market at The Innovation and Design Building in the Seaport neighborhood. Free.

BBQ on the mountain

September 28 - 29, 2019
50 miles west
The BBQFest features roasted pig, oysters, chili, pulled pork, live music, a beer tent, craft vendors, and a farmer’s market at Wachusett Mountain.

Street festival

September 29, 2019
(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 (from Cambridge St. to Brighton Ave.) in Allston. Free.

Dog party on a farm

September 29, 2019
(11 a.m. to 3 p.m.)
9.8 miles NW
Bring your dog to family-friendly Barktober Fest for games, live music, dog trick demos, scavenger hunts, vendors, treats for dogs & kids, and a dog costume contest at Wright-Locke Farm in Winchester. Free.

Country music festival

September 2019
30.7 miles SE
South Shore Country Festival is an all-ages event with food vendors and 10 bands in Marshfield.

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