The events posted on this website are free and/or sponsored by non-profit organizations and agencies. If you are interested in publishing an event, please contact our Public Relations department below:
Phone: 617-725-0878
Email: [email protected]
October Events
SoWa First Friday
Date: October 3rd
Time: 5:00pm– 9:00pm
Location: 450 Harrison Avenue, Boston
Link: https://www.sowaartists.com/events
There’s more happening here than just the leaves changing color. You’ll find every color imaginable in the SoWa building. Come see for yourself at First Friday Open Studios October 3rd, a great way to shop for color. Meet the artists in person. Be the first to see new works. Experience the rewards of buying direct from the makers. You’ll love everything about this art-buying experience.
Fall Festival on The Greenway
Date: October 3rd
Time: 4:30pm– 8:30pm
Location: Rowes Wharf Plaza, High Street & Atlantic Avenue, Boston
Join The Greenway for Fall Fest! Enjoy all the fall fun, including music, food trucks, artisan vendors, glow mini golf, an inflatable obstacle course, free face painting, crafts, and pumpkin decorating! Plus, don’t miss “The Addams Family” (1991), showing on the lawn between Milk Street and India Street at 6:30pm!
Making Strides Breast Cancer Walk
Date: October 4th
Time: 7:30am– 12:00pm
Location: DCR Hatch Shell, 47 David G. Mugar Way, Boston
Link: https://makingstrideswalk.org/BostonMA
The American Cancer Society Making Strides Against Breast Cancer is a celebration of courage and hope, a movement uniting communities to end breast cancer as we know it, for everyone. Whether you’re on a team, leading a team, or even participating solo, get friends and family to join you – more people means more power to end breast cancer.
Douglas Oktoberfest
Date: October 4th
Time: 9:00am– 4:00pm
Location: Main Street, Douglas
Link: https://www.douglasoktoberfest.com/
Mark your calendars – Douglas Oktoberfest is the first Saturday of October and is growing bigger than ever! Enjoy live music, games and rides, delicious food, a lively beer garden, a classic car show, dog races, community fundraisers, and more! It’s a day packed with community fun, local flavor, and festive tradition that you won’t want to miss.
The Climb – Walk for Healing
Date: October 4th
Time: 10:00am
Location: 404 Washington Street, Duxbury
2025 Shatterproof Walk Boston
Date: October 4th
Time: 8:00am
Location: Carson Beach, 180 Mt Vernon Street, Dorchester
Link: https://fundraise.shatterproof.org/events/725
The Shatterproof Walk is an opportunity for communities to come together and walk to end the stigma of addiction while surrounded by friends, family, and loved ones. Honor those we have lost, celebrate those who are living in recovery, and bring hope to the millions living with substance use disorder. The 1.43 mile walk route is accessible & dog-friendly and will have a water station.
Trung Thu Together 2025
Date: October 4th
Time: 3:00pm– 8:00pm
Location: Town Field Park, 1565 Dorchester Avenue, Dorchester
Join us under the glow of the harvest moon for an evening of lanterns, laughter, and community and family love. This is also a wonderful opportunity for young children and youth to learn more about one of the most treasured traditions of the Vietnamese people – Tết Trung Thu (Mid-Autumn Festival). It’s the perfect time to invite your family and friends to come together, share joy, and create new beautiful memories. Town Field Park in Fields Corner will come alive with cultural performances, lantern displays, children’s activities, and delicious foods & drinks from local vendors. All are welcome.
Stoneham 300th – Parade and Drone Show
Date: October 4th
Time: 3:30pm– 7:30pm
Location: Stoneham Town Common, 340 Main Street, Stoneham
Link: https://www.stoneham300.org/300th-parade.html
Join Stoneham 300th for the grand celebration of Stoneham’s 300th year as a town. Parade begins at 3:30 and includes fire trucks and military vehicles, floats, live bands, marchers, performers, antique cars and even a dancing goat. There will be food, music and games on the Stoneham Town Common after the parade, while we wait for dark and Stoneham’s first drone show at 7 pm! Drone show should be visible for a mile or more. Check out the link for more info, maps and parking regulations.
Newburyport’s 5th Annual Indigenous Peoples Day Observance
Date: October 11th
Time: 10:00am– 5:00pm
Location: Waterfront Park, 36 Merrimac Street, Newburyport
Link: https://imaginestudios.org/indigenous-peoples-day/
This free, family-friendly outdoor gathering celebrates traditional and contemporary Indigenous cultural arts, knowledge and diversity, honoring our region’s Indigenous communities and all Native Peoples. This year’s event highlights Indigenous maritime cultural arts traditions in the Dawnland, including the creation, ceremonial launch and paddle of a traditional hand crafted muhsh8n (dugout canoe) made by Darius Coombs and Jonathan James Perry and an ákʷitən (birch bark canoe) made by Jason Pardilla on the Merrimack River!
Apple Country Fair
Date: October 11th
Time: 10:00am– 4:00pm
Location: Brookfield Town Common, Brookfield
Link: https://www.applecountryfair.com/
Join us 2025 for the 46th Annual Apple Country Fair! Held on the Historic Brookfield Town Common, this year’s Fair showcases the work of more than 90 local crafters, artisans and bakers. Fair-goers can browse and buy locally-produced honey, soaps and syrups, hand-knit sweaters and blankets, pottery, carved wooden bowls and décor, beaded jewelry, small batch sweet treats, hand-crafted toys, and other unique gifts. Enjoy live music, lawn games, face-painting, an apple pie baking contest, and more!
Boston Women’s Market at Assembly Row
Date: October 11th
Time: 11:00am– 4:00pm
Location: Assembly Row, 375 Artisan Way, Somerville
Roxbury Russet Festival
Date: October 11th
Time: 12:00pm– 4:00pm
Location: The Shirley-Eustis House, 33 Shirley Street, Boston
Link: https://shirleyeustishouse.squarespace.com/events/2025/roxbury-russet-festival
The Roxbury Russet Festival celebrates an apple cultivar dating back to the seventeenth century, right in Roxbury. Festival activities include crafts, a scavenger hunt, Ask A Master Gardener table, apple cider pressing, Touch-A-Truck with the Boston Fire Department, and resources from other local organizations. Free apple cider donuts and popcorn.
46th Annual Harvard Square Oktoberfest
Date: October 12th
Time: 11:00am– 6:00pm
Location: Harvard Square, Cambridge
Link: https://www.harvardsquare.com/46th-annual-oktoberfest-applications-now-available/
Harvard Square’s flagship event will hit the streets in the heart of the Square on Sunday, October 12th. Live music on multiple stages, countless international food vendors, crafts and of course, festive beer gardens located throughout the Square. Joining again this year: The Filipino American Festival – a celebration of Filipino music, food and culture! Come be a part of a legendary tradition.
The Head of the Charles Regatta 2025
Date: October 16th–19th
Time: See link for race schedules!
Location: Schrafft City Center, 529 Main Street, Charlestown
Best Buddies Boston Friendship Walk
Date: October 18th
Time: 1:00pm– 3:30pm
Location: Schrafft City Center, 529 Main Street, Charlestown
Link: https://www.bestbuddiesfriendshipwalk.org/boston/
The Best Buddies Friendship Walk is the leading event in the country supporting inclusion for people with intellectual and developmental disabilities (IDD). Join more than 50,000 participants at 80 events across the globe to support the Best Buddies programs in schools, workplaces, and communities. You’ll be making the world more welcoming to people with IDD — one friendship, one job, and one life-changing connection at a time. There will be music by DJ Scotty, fun and games, live music, and of course, our celebratory walk! Join us for a fabulous day of fun.
SpicetoberFest
Date: October 18th
Time: 4:00pm– 10:00pm
Location: Boston City Hall Plaza, 1 City Hall Square, Boston
Link: https://www.spicetoberfest.com/
SpicetoberFest is Boston’s hottest fall celebration of bold local flavors and vibrant culture. With support from the City of Boston, SpicetoberFest will celebrate the city’s diverse culinary and cultural fabric by providing a platform for spicy food vendors, urban farmers, chefs, local hot sauce makers, artisan and craft beverage producers, and entertainers to showcase their talents. Food lovers, music fans, spice seekers, families, and festival-goers of all kinds are welcome!
Canton Pooch Parade & Craft Fair
Date: October 25th
Time: 10:00am– 2:00pm
Location: Paul Revere Heritage Site, 2 Rolling Mill Way, Canton
Link: https://paulreveremuseum.org/poochparade2025/
Join the Paul Revere Heritage Site, Canton Lion’s Club, and Marilyn & Company Realty for the 2nd annual Canton Pooch Parade! Don’t miss out on the fun parade of dozens of costumed pets, complete with voting for best costumes! This event will also include other fun such as food trucks, games, bubbles, and shopping from dozens of vendors in the Craft Fair. Spend a lovely day in one of Canton’s jewels: the gorgeous 9-acre park at the Paul Revere Heritage Site!
Boston Book Festival
Date: October 25th
Time: 10:00am– 6:00pm
Location: Copley Square, 560 Boylston Street, Boston
Link: https://bostonbookfest.org/
Celebrating the power of words to stimulate, agitate, unite, delight, and inspire, the Boston Book Festival presents year-round events culminating in an annual festival that promotes a culture of reading and ideas and enhances the vibrancy of our city.
PruBoo
Date: October 26th
Time: 11:00am– 1:00pm
Location: Prudential Center, 800 Boylston Street, Boston