Events

10 free things to do in Boston in October

From outdoor movies to costume parades to the Head of the Charles Regatta.

"MassQ Ball 2025: Color" celebrates cross-cultural arts at the Arnold Arboretum. Arnold Arboretum

4 minutes to read

Whether you’re strolling in search of a Halloween scare or peeping the changing foliage, there are plenty of ways to dive head first into fall in Boston. You can pack in some outdoor music or movies before the cold weather hits, parade around with your (costumed) pooch, and appreciate the arts, all without shelling out a dime.

Here are 10 things to do in Boston for free this October.

1. Experience autumn on the Greenway

Boston’s Rose Kennedy Greenway is getting into the spirit of fall with plenty of
free activities. Fall Fest takes place on Oct. 3 from 4:30 to 8:30 p.m. at
Rowes Wharf Plaza, with food trucks, artisan vendors, tunes from DJ JayVibez,
glow mini golf, an inflatable obstacle course, face painting, crafts, and pumpkin
decorating. You can also check out Greenway Fall Movie Nights on the Color
Commons. Movies begin around 6:30 p.m., and the schedule includes “The
Addams Family” (1991) on Oct. 3, “Goosebumps” on Oct. 10, “Twilight” on Oct. 17, and “Halloweentown” on Oct. 24. Free popcorn and candy will be handed out while supplies last, and you can rent exclusive Greenway blankets for free (with a valid ID or credit card) during the film. (Various locations on the Rose Kennedy Greenway, Boston)

2. Get ‘MassQed’ in creative colors

Centering on the art practice of MassQing (the use of the human face as a
canvas to create living works of art), the MassQ Ball 2025: Color is a large-scale
celebration of ritual, performance, and cross-cultural arts highlighting the diverse artistry of local communities of color. Held on Oct. 4 from 10 a.m. to 4 p.m., this family friendly event at the Arnold Arboretum of Harvard University weaves together music, dance, visual arts, and spoken word with nature and the joy of cross-cultural celebration. Performers activate the conifer section of the Arboretum with sound, sculpture, movement, spoken word, and other arts, and attendees can have their faces painted. (125 Arborway, Boston)

3. Get in front of your favorite big name comic book creators

Wicked Comic Con comes to Boston for an entire day dedicated to comic books,
their creators, cosplay, and artwork. During this event held on Oct. 5 from 10 a.m. to 5 p.m. at the Westin Boston Seaport District, you’ll stroll the space to view dozens of vendors and artists who will have collectibles, toys, cards, comics, cosplay items, and games on display and available for purchase. You’ll also have the chance to meet plenty of professional all-star DC and Marvel comic book creators and cosplay favorites. (The Westin Boston Seaport District, 425 Summer St., Boston)

4. Celebrate Indigenous People Day

Honor Indigenous American peoples and commemorate their histories and
cultures on Oct. 13 with free access to museums around Boston. The Museum of Fine Arts, Boston (MFA), whose collection of Native American artworks is one of its hidden treasures, is offering free admission and special events during an open house that day from 10 a.m. to 5 p.m., while the Institute of Contemporary Art (ICA) also offers free admission to view its galleries (you can grab these tickets on Oct. 12 at 10 a.m.). (Various locations around Boston)

5. Watch a Halloween favorite under the stars

The Anchor takes on witchy season with a screening of “Hocus Pocus” on Oct. 15 at 9 p.m., part of its Watch Wednesdays movie series. Settle into a cozy lounge chair on Charlestown’s waterfront patio with unbeatable views of Boston Harbor. There’s a menu of food and drinks for purchase, or just sit back and chill for some classic spooky seaside vibes. The event is open to all ages. (1 Shipyard Park, Boston)

Watching the Head of the Charles Regatta from one of the many bridges is a well-worn tradition.

6. Cheer as teams row, row, row their boats

Consider the Head Of The Charles Regatta as a who’s who of rowing. Held this
year Oct. 17-19, the world’s best crew teams challenge each other to the ultimate
rowing competition on the Charles River. Grab a spot early between the
Anderson and Weeks bridges, the halfway point of the race, for the best views.
Between competitions, which run from 8 a.m. to 5 p.m., stroll the Weld Exhibition for delicious local flavors, free samples, and official Regatta programs and merchandise. (Charles River, Boston)

7. Bring your pooch to a spooky dog park

Dress up your pets in their cutest costumes for a spooktacular day at the park on Oct. 18 from 9 a.m. to 1p.m. During Howl-O-Ween, there will be a pet costume contest parade (complete with pawsome prizes for four parades – family at 10 a.m., small dogs at 10:45 a.m., big dogs at 11:30 a.m., and owner/dog paired costumes 12:15 p.m.), dog-friendly pumpkin spice lattes, and shopping from local pet friendly vendors. (Peter’s Park Dog Park, 1205 Washington St., Boston)

8. Dive into your favorite book genre

Honoring the power of the written word, the Boston Book Festival culminates a
year-long schedule of events with its 17th annual festival. Held in partnership
with WGBH on Oct. 25 from 10 a.m. to 6 p.m., the event promotes a culture of
reading and hosts several authors discussing their chosen genres, including
mystery, fiction, non-fiction, art history, young adult, and science and society.
(Copley Square, Boston)

9. Say ‘I do’ to a bridal expo

Have a big day coming in 2026? Whether you’re just starting the planning or
you’ve already made a few decisions, discover all things wedding,
honeymoon, and home on display at the Great Bridal Expo on Oct. 26 from noon to 4 p.m. Enjoy giveaways, prizes, live orchestra, DJs, and sample catering options while exploring aisle after aisle of exhibits. (Westin Boston Seaport District, 425 Summer St., Boston)

10. Enjoy Halloween at the Pru

More than 30 stores and restaurants at the Shops at Prudential Center sponsor
the PruBoo, an annual trick-or-treat event that benefits Boston Children’s
Hospital this year. Dress the kiddos in their cutest Halloween outfits and enjoy
trick-or-treating, face painting, magic shows, pumpkin decorating, live musical
performances, and more from 11 a.m. to 1 p.m. on Oct. 26. While it’s $5 donation per child (12 and under) to purchase a trick or treat bag, all other activities are free. (Prudential Center, 800 Boylston St., Boston)

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