Free Things to Do in Boston, October 2015

This month is packed with free events, including the Head of the Charles Regatta, Canine Promenade, Lawn on D Punkin' Fest, Honk! Festival, and more.

free events boston october 2015

The Lawn on D Punkin’ Fest / Photo Courtesy of The Lawn on D


A biannual event, ArtWeek is a ten-day showcase of creativity. While some of the workshops can get pretty pricey, there are many free ones offered as well. Encompassing a wide range of artistic endeavors, ArtWeek allows you to check out tours and open studios, get your photo taken like a model, try your hand at improv, and more. Open up your mind to out-of-the-box forms of creative expression and impress your friends with the new artistic skills you’ve learned at this year’s events.

Check website for various events, through October 4,

Boston Fashion Week

The annual Boston Fashion Week features a lineup packed with displays of artistry by local talents. While many of the events require you to pay up for admission, there are also a few that are free and open to the public, including an exhibition of non-textile garments created by students from Massachusetts College of Art and Design, a display of 3D-printed jewelry presented by Design Museum Boston, and a designer runway show from L’Elite Occasions & Musette Bridal.

Check website for various events, through October 3,

Lunch Break on D Featuring Berklee Summer in the City

The Lawn on D has been hosting free afternoon concerts every Friday this summer, enticing you to spend your lunch break soaking up the sun, enjoying offerings from local food trucks, and checking out rotating art exhibitions and live music. The series is winding down for the season, but there are a couple of shows left, with Cherry Mellow and Madeline Rae set to perform. 

Free, Fridays, October 2 and 9, Lawn on D, 420 D St.,


Described as “a weeklong series of events and experiences,” HUBweek is brought together by the Boston Globe, MIT, Massachusetts General Hospital, and Harvard. It’s a celebration of the art, science, and technology endemic to Boston, allowing all of the originality and inventiveness to be shown in festivities and conferences throughout the city. HUBweek encompasses a wide array of topical events, including the Let’s Talk About Food Festival (a compendium of chefs exploring and exposing the reality behind the foods we eat), De-Stress Boston (an outdoor group class on stress reduction techniques) and ILLUMINUS (a “nighttime contemporary art festival” that will transform Lansdowne Street into an art exhibition and Fenway’s Green Monster into a multidimensional projection screen). While most of the events are free, some do require registration.

Check website for various events, October 3-10,

Liquid Courage Comedy Club

Slumbrew, otherwise known as Somerville Brewing Company, has decided to combine two things Bostonians love: standup comedy and beer. Laugh along with rising comedians in Slumbrew’s brewery and destination-taproom—all while drinking as much beer as you like. All shows are 21+.

Free, Slumbrew, October 4, 11, and 25, 15 Ward St., Somerville,

Allston Village Street Fair

Built on the concept of diversity and called “Boston’s hippest multicultural festival,” the Allston Village Street Fair has something for everyone. It’s a day packed with excitement, featuring an international food court, a public street art mural area, and two outdoor stages. This year’s theme is Mardi Gras, so grab your beads and get ready to have a blast in one of Boston’s most vibrant neighborhoods.

Free, Sunday, October 4, 12-6 p.m., Harvard Avenue, Allston,

free events boston october 2015

Seed and Feed Marching Abominable at Honk! Fest / Photo Courtesy of Bill Manley

Honk! Festival of Activist Street Bands

This is what happens when you combine brass bands and progressivism—now in its 10th year, the three-day Honk! festival brings together artists from all across the country to dance, celebrate, and root for change. “We exist to try to use our music to do positive things in the community,” says Ken Field, a member of the Honk! organizing committee and a musician in the Second Line Social Aid and Pleasure Society Brass Band. Honk! kicks off on Friday, October 9, with a lantern parade and dance showcase and lasts until Sunday, October 11, culminating in a large parade from Somerville to Cambridge. Cheer on as the brass bands join local community groups, artists and activists—all promoting a variety of causes like environmental protection and an end to racism—to march from Davis Square to Harvard Square. 

Free, Friday, October 9, to Sunday, October 11, Davis Square, Somerville,

Lawn on D Punkin’ Fest

The forecast for October: chilly with a high chance of the Lawn on D still dominating your Instagram feed, although photos of the circular swings might be overtaken with snapshots of jack-o’-lanterns. On October 10, head on over to the park in Southie and pick a free pumpkin from the D Street Punkin’ patch, carve it, and add it to a gigantic illuminated sculpture. Holding true to its creation as a public interaction and art space, the Lawn on D’s Punkin’ Fest is part seasonal celebration and part community art project. The large jack-o’-lantern sculpture will use high-tech lighting, illuminating the pumpkins in sync with music. There will also be pumpkin bowling, face painting, and pumpkin carvings done by local artists, making it an event everyone can enjoy.

Free, Saturday, October 10, Lawn on D, 420 D St.,

Sam Adams New England Stein Hoisting Finals

It’s simple, really: Hold up a full-liter stein longer than anyone else. The annual competition searches for the best and strongest all across the country, ending later this fall on Jimmy Kimmel Live and sending the two champions to Oktoberfest in Munich, Germany. We know you want someone local to win (how exciting would that be?) so be sure to cheer on the New England finalists at Ned Devine’s.

Free, Sunday, October 11, Ned Devine’s, 1 Faneuil Hall Marketplace,

Columbus Day Parade

Witness the hodgepodge of music, saints, duck boats, and entertainers that makes up the annual Columbus Day parade. It’s a three-tiered celebration of famed Italian explorer Christopher Columbus, Italian heritage, and Massachusetts military units.

Free, Sunday, October 11, 1-3 p.m., kicks off at City Hall Plaza and continues into the North End,

Opening Our Doors Day

Aptly named, the Fenway Cultural District is quite literally opening its doors this fall. With the goal of showing off the culture and artistry inherent to this neighborhood, the 21 member institutions of The Fenway Alliance invite the public to come take a peek inside to see what they’re up to. Free admission to some of Boston’s best museums, indoor kite flying, free cupcakes from Oakleaf Cakes, and musical performances are only some of the features of the day’s exciting lineup.

Free, October 12, kick-off at 10 a.m. at the Christian Science Plaza,

Columbus Day Celebration in Columbus Park

Stop by Columbus Park on the North End waterfront to celebrate the man it’s named after. Expect fun local performers, family activities and, of course, gorgeous views of the Harbor at this holiday event.

Free, Monday, October 12, Christopher Columbus Park,

School of Rock

Interested in learning an instrument? No, Jack Black will not pose as a substitute teacher and help you finagle your way into a battle of the bands at this School of Rock, but you will be given a free music lesson. In partnership with local nonprofit music-lending library The Musary, the School of Rock sets up shop at the Charles River Bistro on the second Tuesday of every month. Here, credible instructors wait for you to stop by and learn how to rock.

Free, Tuesday, October 13, Charles River Bistro, Hatch Shell on the Esplanade,

2015 Kickstarter Film Festival

With almost $300 million donated to independent filmmakers, Kickstarter has helped support the creation of seven Academy Award nominees and one winner, as well as many of the films shown at the Sundance Film Festival. For their next feat, Kickstarter will host screenings across the country—locally at the Brattle Theatre—to display some of the outstanding work it’s helped fund. It’s a program packed with everything from feature films to animation to documentaries to hits from Sundance.

Free, Thursday, October 15, the Brattle Theatre, 40 Brattle St., Cambridge,

Fort Point Open Studios

Credited as being Boston’s original open studios event, Fort Point Open Studios is now in its 36th year and includes more than 150 local artists who have turned waterfront warehouses into homes for their work. The showcase encompasses a wide array of creativity, featuring painting, sculpture, handmade jewelry, performance art, photography, and more. In conjunction with the event, the Fort Point Open Studios will present “Who Wears Wool” by Hilary Zelner, a new temporary art installation anchored in the Fort Point Channel.

Free, Friday, October 16, to Sunday, October 18, Fort Point,

free events boston october 2015

Photo from the 2014 Head of the Charles by Olga Khvan

Head of the Charles Regatta

Another year, another spectacle of top-notch athletes competing in the world’s largest regatta. Watch the best rowers in the country race to the finish line while enjoying food, shopping, and beautiful views along the Charles River.

Free, Saturday, October 17, to Sunday, October 18, Charles River,

Massachusetts Independent Comics Expo

Whether you’re an avid comic book collector or a casual reader, the Massachusetts Independent Comics Expo has you covered. Unlike other comics shows, MICE’s primary focus is on cartoonist art. A joint project between the Boston Comics Roundtable and Lesley University College of Art and Design, MICE hosts workshops, panel discussions, and guest creators.

Free, Saturday, October 17, to Sunday, October 18, University Hall at Lesley University, 1815 Massachusetts Ave.,

Halloween Pumpkin Festival on the Boston Common

We know you’ll be spending the month carving out some pumpkins—it wouldn’t be October without them. At the mayor’s annual Halloween Pumpkin Festival, you can bring yours over to the Common, have it illuminated, and watch it light up the night with dozens of others as it floats along Frog Pond. Giveaways, refreshments, and a chance to show off that sweet jack-o’-lantern you’ve been working on—sounds like a pretty good family outing.

Free, Saturday, October 17, 5:30-7:30 p.m., rain date is Sunday, October 18, Boston Common Frog Pond,

Boston Book Festival

The perfect celebration for literature lovers, Boston Book Festival is an annual event for aspiring authors and bibliophiles alike. Enjoy a huge lineup of guest speakers, writers’ workshops, and a street fair featuring a variety of independent publishers and literary magazines. The keynotes by Margaret Atwood and Amanda Palmer are ticketed, but the rest of the two-day event is free to the public.

Free, Friday, October 23, to Saturday, October 24, Copley Square,

Boston Vegetarian Food Festival

Join food providers and top national speakers and chefs at a festival giving definitive proof that vegetarian food can be quite tasty. Explore exhibits about everything from grocery stores to protecting the environment, while learning how appealing meals without meat can be. There’s also plenty of free food sampling, making this event both educational and delicious.

Free, Saturday, October 24, to Sunday, October 25, Reggie Lewis Athletic Center, 1350 Tremont St.,

Rock and Run Festival

Urban RAID and Radio 92.9 have teamed up once again to bring the combination 5K obstacle race and music festival back to town. Although you have to register to compete, the festival at the finish line is free and open to the public. This means that even non-runners have reasons to race to the finish: live music and beer. Cheer on friends and strangers alike at this year’s Rock and Run.

Free, Saturday, October 24, City Hall Plaza,

free events boston october 2015

Photo from the 2014 Canine Promenade by Olga Khvan

Canine Promenade

Why wouldn’t you want to spend the day at a parade of dressed up dogs? The annual Canine Promenade, now in its fifth year, is a half-mile stretch around the Esplanade full of cute, costumed pups. Yes, you read that right. A dog parade. What more do you need?

Free, Sunday, October 25, 12-2 p.m., Fiedler Field on the Esplanade,

South End Open Market @ SoWa Halloween Costume Contest

October means that the South End Open Market is coming to a close for the season. But no need to fret, as October also means that it’s time for their 12th annual Halloween costume contest. This year, the event, titled “Area 460,” is alien-themed. “Our vendors and customers go all out every year with amazing, creative and handmade costumes, and the turnout is excellent,” says Leah Mohammed, Executive Assistant to the CEO of New England Open Markets. While shopping around more than 150 vendors and eating delicious local food, customers have a chance to win cash prizes for their costumes. The vendors will also be decked out and competing, creating a fun, spooky atmosphere all around.

Free, Sunday, October 25, 460 Harrison Ave.,