26 Free Things To Do In Boston This September

Dorchester Bike & Brew Festival
Wednesday, September 13, 2017: 7-9:30pm

Peabody Square Ashmont, Dorchester Center

The Dorchester Bike & Brew 2017 is a family friendly community festival designed to showcase the growing cycling community in #Dorchesterand the burgeoning Boston brewery scene, along with food trucks, live music, DIY bike repair demos, giveaways, etc.

The event is held on Peabody Square West Plaza, and a small portion of Talbot Ave (between Dorchester and Welles Ave) closed to vehicular traffic for the duration of the festival. It is free to attend, with food and beverages available for individual purchase.

Music: We will again feature a fun for all ages opening act, this year Second Line Social Aid and Pleasure Society Brass Band at 7:00 and we are excited to confirm that The Nephrok! Allstars will headline the event (funk & soul), with their sets starting at 7:50.

Food Trucks: We plan to host three savory food trucks (Jamaica Mi HungryBaby’s Bonetown BBQSheherazad Truck) and one sweets truck (TBA) to maximize your dinner options, and we are excited to have theBoston Water and Sewer Commission H2Go mobile water station join us again!

Beer Garden: Dorchester Brewing Company is the exclusive brewery partner for this year’s Dorchester Bike & Brew — they will be hosting their signature beer garden in an age-verified 21+ space on site. The beer garden will also again feature assorted cider offerings fromDowneast Cider House (an East Boston Main Streets business). A portion of the proceeds from all beverage sales will support Greater Ashmont Main Street’s programming year round.

Vendors/Community Information Tables beyond the co-hosts: Roxbury RidesBlack Girls Do Bike (Boston), Spokehouse – Bowdoin Bike School,Martin Richard FoundationLivableStreets AllianceHarbor Health Services, Inc.Bikes Not BombsWalkBostonLevel Solar, and MBTA Transit Police Bike Unit, with additional services available as well, such as the City Hall to Go truck and Boston Public Library‘s BiblioCycle on site and family friendly fun like our lawn games, bubble give aways, glow in the dark chalk, and Balloons Extraordinaire on site for adorable balloon creations.


Lets Dance Boston
Wednesday, Sep 13, 2017: 5:00pm – Sunday, Sep 17, 2017: 10:00pm

Dewey Square
600 Atlantic Ave
Boston, Massachusetts 02210

Dreaming of dancing out under the stars? The Celebrity Series of Boston invites dancers of all ages and abilities to grab their dancing shoes and head to the Rose Kennedy Greenway September 13-17, 2017 for the return of Let’s Dance Boston, produced by the Celebrity Series of Boston.

The event will include 4 consecutive nights of dynamic live music and a special Sunday afternoon dance along. There will be 5 different live bands throughout the event preceded by lessons from expert dance instructors. Dance styles confirmed to date include salsa, swing and on Sunday afternoon Klezmer folk dance, produced in association with the Jewish Arts Collaborative.

The full schedule as well as the live bands will be announced later this summer. All instructions and open dance sessions are free and open to the public

MFA Sunset Cinema: ‘Get Out’
Thursday, Sep 14, 2017 6:30pm – 10:00pm

Museum of Fine Arts Boston
465 Huntington Ave
Boston, MA 02115

MFA Film is thrilled to present Sunset Cinema, an open-air theater with free monthly film screenings on the Museum’s Huntington Avenue lawn. In July, kick off the Boston French Film Festival with the razor-sharp comedy Divorce, French Style; in August, Paul Newman stars in the gritty prison drama Cool Hand Luke, part of the series Feed Your Head: Films from 1967; and in September, we’re teaming up with the Roxbury International Film Festival to present the groundbreaking horror flick Get Out.

Lawn games, music, and art-making activities begin at 6:30 pm. All films start at sundown, around 8 pm. No ticket is required. We suggest bringing a blanket or low chair, a picnic supper, and nonalcoholic beverages to enjoy during the film. Beer, wine, and snacks will be available for purchase.

MFA Film and the Roxbury International Film Festival present a special screening of Jordan Peele’s groundbreaking horror film, Get Out. The film follows a New Yorker named Chris (Daniel Kaluuya) who hits the road with his new girlfriend, Rose (Girls’ Allison Williams), for weekend getaway at Rose’s childhood home. This is Chris’s first time meeting Rose’s parents, and at first he interprets the family’s overly accommodating behavior as a nervous attempt to show their acceptance of their daughter’s interracial relationship. But as the weekend progresses, a series of increasingly disturbing incidents lead him to uncover a truth beyond his wildest nightmares.


Country In The City
Thursday, Sep 14, 2017 7:00pm – 9:00pm

City Hall Plaza
1 City Hall Square
Boston, MA 02201 

Join Mayor Martin J. Walsh and Country 102.5 for the second Country in the City concert! Enjoy a live country music performance (and some delicious food truck snacks) at City Hall Plaza. It’s free! More details to follow.

Cambridge PARKing Day
Friday, Sep 15, 2017 8:00am – 6:00pm

Parking spots across Cambridge
Cambridge, MA

55 groups are transforming over 120 parking spots into something else for the day in our official City of Cambridge PARK(ing) Day celebration!

Join us to ride along new separated bike lanes, hear about coworking spaces in Central Square, learn about wildlife in Cambridge, celebrate Vision Zero, and try out new technologies being developed in our community!


Boston Freedom Rally
Friday, Sep 15, 2017 3:00pm – Sunday, Sep 17, 2017 6:00pm

Boston Common
84 Beacon St
Boston, MA 02108 

Although occasionally referred to as “hempfest” by some, the Boston Freedom Rally is the official name of the largest annual gathering of pro-marijuana supporters on the East Coast, and is the second largest festival of it’s kind in the world, surpassed only by Seattle’s Hempfest.

The rally is organized by the Massachusetts Cannabis Reform Coalition (MassCANN), the state affiliate of the National Organization for the Reform of Marijuana Laws (NORML) also known as MassCann/NORML.


Cathedral Greek Festival
Friday, Sep 15, 2017 12:00pm – Sunday, Sep 17, 2017 8:00pm

Annunciation Greek Orthodox
Cathedral of New England
514 Parker St
Boston, MA 02120

Greek Festival at 162 Goddard Ave. Sponsored by the Cathedral and its sponsors and frieds of the Cathedral. Greek cuisine, Greek Pastries, Pumpkin Fest for family members of any age, our annual festival raggle, lots of music and dancing to the tunes of Orfeas and Makredes Ensemble, Athas Borthers DJ music and the Metropolis Dance Groups. Boutigues of all kinds and our Taverna on the lawn patio behind the mansion that will house Attic Treasures. Kafenio inside the Center Hall with plenty seating.


Mixfest 2017
Saturday, Sep 16, 2017 11:00am – 6:00pm

Hatch Memorial Shell
1 David G Mugar Way
Boston, MA 02108

Mix 104.1’s MixFest is New England’s premier FREE music event! This year, Mix welcomes Kelly Clarkson, Blondie, and Andy Grammer to the stage at the DCR Hatch Memorial Shell on Boston’s Charles River Esplanade !

Gates open at 11am. Music starts around 2pm.

Admission is free, but we encourage you to get there early!


Social Fitness Festival
Saturday, Sep 16, 2017 11:00am – 6:00pm

City Hall Plaza
1 City Hall Plaza
Boston, MA 02176

Mayor Martin J. Walsh and the City of Boston’s Office of Tourism, Sports, and Entertainment, in partnership with Blue Cross Blue Shield of Massachusetts and in collaboration with the City’s Property Management Department, announce the second annual Boston Social Fitness Festival! This free, day-long celebration of getting Boston moving will feature numerous participatory events to encourage Bostonians of all ages to move, cycle, play, and dance together.

South Boston Street Festival
Saturday, Sep 16, 2017 11:00am – 4:00pm

East Broadway
between I and L Streets
South Boston, MA 02127

Live entertainment on 2 stages • Over 100 Local Merchants, Artists and Organizations
Great Food • Dance Performances • Children’s Activities • Pooch Friendly

3rd Annual Roslindale Porch Fest
Saturday, Sep 16, 2017 1:30pm – 5:30pm

Porches around Roslindale
Roslindale, MA

An afternoon of free music across the porches of Roslindale! Eclectic music and family-friendly alcohol-free atmosphere.

Oktoberfest 2017 at Night Shift Brewing
Saturday, Sep 16, 2017 11:00am – 11:00pm

Night Shift Brewing
87 Santilli Highway
Everett, MA 02149

NSB Oktoberfest is back for the 3rd year running! Our parking lot will be transformed into a traditional German-style beer garden, complete with brass bands, food vendors, communal drinking tables, and lawn games.

Saturday, Sep 16, 2017 11:00am – 5:00pm

Fenway Park
4 Yawkey Way
Boston, Massachusetts 02109

Now in it’s 32nd year, CollegeFest is a back-to-school tradition in Boston, and is the most attended back-to-school event in New England. This is an opportunity for students to spend the day at Fenway Park free of charge while enjoying live music and engaging with local, regional and national brands/vendors.


American Field Boston
Saturday, Sep 16, 2017 11:00am – Sunday, Sep 17, 2017 6:00pm

Innovation and Design Building
Drydock Avenue
Boston, MA 02210

American Field is a pop-up market of authentic brands that connects consumers directly with makers ad returns to Boston this September at the Innovation and Design Building. The American Field Movement raises awareness for quality brands and strives to inform consumers, making it easy to decide where to spend their money. It was created by Mark Bollman, founder of Ball and Buck, in 2012 and highlights brands committed to quality and innovation in design.


South End Open Studios
Saturday, Sep 16, 2017 11:00am – Sunday, Sep 17, 2017 6:00pm

Various locations in the South End
South End
Boston, MA 02118

Since 1986, South End Open Studios has provided a once-a-year, back-stage pass that invites visitors to explore and enjoy the creative environment of Boston’s largest and most exciting community of working artists. With locations throughout the South End neighborhood, over 200 artists will showcase their work, with local galleries displaying work by national and international artists. Free shuttle service will be available to transport visitors to studios and galleries.

Boston Local Food Festival
Sunday, Sep 17, 2017 11:00am – 5:00pm

Rose Kennedy Greenway
Atlantic Ave & High Street
Boston, MA 02110

For one spectacular day each year, SBN transforms the Rose Kennedy Greenway and the City of Boston into the nation’s largest local & sustainable food hub! Boston Local Food Festival is a free outdoor festival that showcases farmers, local restaurants, food trucks, specialty food producers, fisher folks, and organizations focusing on healthy food and fitness from New England. The festival also features lively chef & DIY demos, a seafood throwdown competition, diverse music and performances, family fun zone and more.

Revels River Sing: A Family Celebration of the Autumnal Equinox
Sunday, Sep 17, 2017 5:00pm – 7:30pm

Winthrop Park in Harvard Square & by the Weeks Footbridge
Memorial Drive & DeWolf Street
Cambridge, MA 02138

JOIN THOUSANDS OF VOICES IN SONG as we wave goodbye to summer and welcome in the fall at our14th annual Autumnal Equinox celebration in Cambridge! Pre-show festivities in Harvard Square begin at 5pm followed by a puppet-filled Parade to the Charles for communal singing and more led by The Revels Chorus, great guest soloists, children from Boston City Singers and a fabulous folk band.

Boston Startup Week
Monday, Sep 18, 2017 9:00am – Friday, Sep 22, 2017 8:00pm

Surrounding areas
Boston, MA

Boston Startup Week is a free, five-day series of events celebrating, educating, and connecting Boston’s startup community. Whether you’re an aspiring founder, the leader of a growing company, or someone who wants to work with startup teams, Boston Startup Week has an event for you.

Full schedule of events:


Somerville Fluff Festival 
Saturday, Sep 23, 2017 3:00pm – 7:00pm

Union Square
90 Union Sq
Somerville, MA 02143

Join us for the celebration of the 100th anniversary of Fluff, invented right here in Somerville’s Union Square in 1917 by Archibald Query. This madcap, fun-filled festival draws approximately 15,000 people and is cited as one of the reasons why Lonely Planet named Somerville in the top 10 “Best In The US” travel destinations for 2016.

The 12th annual “What the Fluff” Festival will feature musical performances, a cooking contest, Fluff-themed games, activities, antics and fun for every age, and Fluff treats of every sort.


Everett Village Fest 
Saturday, Sep 23, 2017 3:00pm – 9:00pm

Santilli Highway
Everett, MA 02149

Mayor Carlo DeMaria and the City of Everett is pleased to announce that we will be celebrating our 3rd annual Village Fest, taking place on Saturday, September 23rd, 2017 from 3 – 9 PM at Santilli Highway. Come enjoy Boston’s best food trucks, full-line up of music entertainment all day long, and an international acclaimed headliner George Clinton and Parliament Funkadelic. Our headliner band is sponsored in part by Wynn Boston Harbor and Craft Brewers Guild.


Boston Festival of Indie Games 
Saturday, Sep 23, 2017 9:00a – 7:30p

Johnson Athletics Center
120 Vassar St
Cambridge, MA 02139

The Boston Festival of Indie Games is the biggest celebration of independent tabletop and video games in New England. BostonFIG is an inclusive, welcoming environment filled with family-friendly activities and games of all sorts that you won’t see anywhere else. Saturday, September 23, 2017 will mark our sixth annual celebration of independent game development.


Smithsonian Museum Day Live!
Saturday, Sep 23, 2017 8:00am – 5:00pm

Surrounding areas
Boston, MA

The Museum Day Live! ticket provides free admission for two people.

Participating museums include the Museum of Fine Arts, the Museum of African American History, Harvard Art Museums, the Harvard Museum of Natural History, and more.

Museum Day Live! is an annual celebration of boundless curiosity hosted by Smithsonian magazine. Participating museums and cultural institutions across the country provide entry to anyone presenting a Museum Day Live! ticket.


Jamaica Plain Open Studios
Saturday, Sep 23, 2017 11:00am – Sunday, Sep 24, 2017 6:00pm

Jamaica Plain
Surrounding areas
Boston, MA. 02130

Jamaica Plain Open Studios, the premiere annual arts event in one of Boston’s most eclectic neighborhoods, is returning in 2017 for its 24th year. Open Studios is an opportunity to take a rare public peek at some private spaces. The free event showcases the artwork of up to 200 artists at 40 sites including artists’ studios, the historic Eliot School, the Sam Adams brewery complex, Mozart Park in Hyde Square and more. It runs from 11 a.m. – 6 p.m. over the weekend of September 23-34, 2017


Allston Village Street Fair 
Sunday, Sep 24, 2017 12:00pm – 6:00pm

Harvard Ave between Brighton Ave and Cambridge St
Harvard Ave & Brighton Ave
Allston, MA

For a neighborhood so youthfully vibrant and culturally diverse, Allston gets a bad rap. It breeds creativity and a modern bohemia rarely seen in other areas of the Hub. Sunday, the Parents and Community Build Group’s Allston Village Street Fair shows off exactly what Allston offers year-round: a litany of live performances, several local businesses taking to the streets and thousands of people coming together in one giant party highlighting more than 30 live performances from 2 outdoor stages and street performers, vendors, artists, and craftspeople show off their wares; and Harvard Avenue morphs into Bourbon Street for this year’s Mardi Gras theme. Grab some beads, rock out and have some fun, Allston-style.

Berklee Beantown Jazz Festival  
Saturday, Sep 30, 2017 12:00pm – 6:00pm

Columbus Ave between Mass Ave + Burke St
Columbus Ave & Massachusetts Ave
Boston, MA

The Berklee Beantown Jazz Festival is Boston’s biggest block party—a free, annual, outdoor public concert that has delighted hundreds of thousands of music lovers over the years with its host of jazz, Latin, blues, funk, and groove performances, along with KidsJam, an instrument petting zoo, and an array of food vendors. Each year, the festival is the place to be in Boston on the last Saturday of September as the community comes together in a bond forged in the joy of great live music.

The festival offers world-class music on three stages, phenomenal food and drink, arts, crafts, and unique gifts. We look forward to seeing you for Boston’s best free outdoor concert.


New England Indonesian Festival  
Saturday, Sep 30, 2017 12:00pm – 6:00pm

Copley Square
560 Boylston St
Boston, MA 02116

The New England Indonesia Festival (NEIF) is an event annually held in the hotel’s Back Bay neighborhood that promotes Indonesian culture to the New England community, which includes the state of Massachusetts and its neighboring states. Since its launch in 2013, NEIF has been held in Copley Square, a large open venue at the heart of Boston, and has attracted over 5,000 attendees annually.

Jonathan Holden

The author Jonathan Holden

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