Boston events September 2019. Things to do in Boston.

Best events for 12 months

Boston events September 2019

Country fair

September 1, 2019
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
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
35 miles NE
Gloucester Schooner Festival begins with a block party on Friday evening. Saturday includes Maritime Gloucester 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.

Medieval fair

September 1 - Oct. 20, 2019
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 and October 14, 2019.

Labor Day festival

September 2, 2019
28 miles north
Bread & Roses Heritage Festival is “a multi-cultural, multi-ethnic, labor and social justice open-air arts & music festival” with food vendors, arts & crafts, entertainment, afternoon walking tours & trolley tours, giant puppets (4:20 p.m.), pony rids, and a kids’ zone in downtown Lawrence. Free.

Free movies in parks

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

Scrapbook Expo

September 6 - 7, 2019
35 miles west
Scrapbookers will find classes, vendors, and crop parties at the Stamp & Scrapbook Expo at Royal Plaza Trade Center in Marlborough.

Boston Night Market

September 7, 2019
(4 to 10 p.m.)
0.1 miles west
Shop for food and merchandise, visit the beer garden, hear DJ music, and play games at Boston Night Market in City Hall Plaza. Children age 8 and younger are free.

Jamaica Plain music festival

September 7, 2019
(12 to 7 p.m.)
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 northeast of Jamaica Pond. Free.

Blues and Brews

September 7, 2019
(gates 1 p.m., music 2 p.m.)
31 miles NW
A ticket to Blues N Brews gets you 10 beer samples from 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 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, target shooting, kids’ games, German food, beer, wine, and crafts in a covered pavilion at the German club in Walpole. Children younger than age 12 are free. No pets.

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 in October (plus Oct. 6 & 31).

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. Children younger than age 12 are free.

Beer-tasting cruise

September 12, 2019
(5:30 p.m.)
0.5 miles SE
Boston Harbor Thirsty Thursday Cruise features “2 or 3 different local breweries providing tastings of their best beers while crusing Boston Harbor” for 75 minutes, departing from 60 Rowes Wharf for age 21+.

Free fitness festival

September 14, 2019
(7 a.m. to 3 p.m.)
0.1 miles west
Move, cycle, play, and dance at Boston Social Fitness Festival, which 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 in The Murr Center at Harvard. Children age 12 and younger are free.

Beer at the zoo

September 14, 2019
(5 to 7:30 p.m.)
8.2 miles north
Taste beer from 27 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 43 miles.

Food festival

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

Free harbor cruise

September 16 - Oct. 20, 2019
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 answer questions 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, 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 lunch and awards, with a boat ride included.

College student festival

September 21, 2019
2.5 miles SW
CollegeFest is a back-to-school event with live music, entertainment, prizes, and giveaways for students at Fenway Park, sponsored by Army ROTC. 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
(3 to 7 p.m.)
2.8 miles NW
What the Fluff? celebrates marshmallow cream with games (Sticky Musical Chairs, Marshmallow Toss, Fluff Jousting), treats, a cooking contest, a kids’ area, and live music at Union Square in Somerville, where Fluff was invented in 1917. Rain date Sept. 22, 2019. Free.

Welcome autumn

September 21, 2019
6 miles west
Say goodbye to summer and celebrate the first day of fall with crafts, choruses, dancing, a puppet parade, a sing along, a beer garden, and concessions during Revels RiverSing at Herter Park Amphitheater in Allston. 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
(2 to 5:30 p.m.)
67 miles SE
Sample 300 beers from 100 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 printed map to visit studios of 200 local artists plus local galleries during South End Open Studios. Free.

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. Pre-events begin September 9.

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.
  • Sept. 26 - Hunter Hayes and High Valley

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+.

Haunted ski area

September 27 - Nov. 2, 2019
29 miles NW
Witch’s Woods has seven attractions, including a haunted hayride and a nightmare mansion, at Nashoba Valley Ski Area. See schedule.

Discount tickets

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. Closed Mondays and Tuesdays.

Discount tickets

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
(10:30 a.m. to 4:30 p.m.)
3.6 miles NW
Let’s Talk About Food has cooking demonstrations, food talks and panels, samples, local chefs, and nutritionists in Harvard Science Center Plaza. Free.

Blacksmith festival

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

Free music festival

September 28 - 29, 2019
(11 a.m. to 6 p.m.)
0.1 miles west
The Boston Local Music Festival features 50 local bands on three stages, a beer garden, food vendors, and artists in City Hall Plaza. Free.

Buy American

September 28 - 29, 2019
2.4 miles SE
Shop from vendors selling American-made goods and foods at 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 (Saturday), pulled pork (Sunday), live music, a beer tent, craft vendors, keg tossing, a tattoo contest, 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 Barktober Fest for live music, dog trick demos, activities for dogs and kids, vendors, a dog costume contest, and a beer garden at Wright-Locke Farm in Winchester. Children age 12 and younger are free.

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