October is packed with can’t-miss events that bring the city to life. Whether you're cheering at the Head of the Charles Regatta, dancing through the HONK! Festival, or celebrating the season at an Oktoberfest, there's something for everyone to enjoy this month. Discover the top events in the Greater Boston area this October below.

Top Events in October

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Purpose Sep 15

WINNER! Tony Award for Best Play WINNER! Pulitzer Prize for Drama Winner of the 2025 Pulitzer Prize and a smash hit on Broadway, Purpose is the explosive and wildly entertaining new play from Tony winner Branden…

Freedom Trail Lantern Tour Sep 17
  • Departs from Boston Common Visitor Center

The official Freedom Trail Lantern Tour offers a first of its kind experience in uncovering the grim, macabre history and mystery of the Freedom Trail! Fatal sword duels, the grave of a ruthless pirate, scenes of…

Wicked Sep 23

So much happened before Dorothy dropped in. WICKED , the Broadway sensation, looks at what happened in the Land of Oz... but from a different angle. Long before Dorothy arrives, there is another young woman, born with…

Harvard Art Museums at Night Sep 24

Registration: Walk-ins welcome, but you may register here. Fee: This is a free event. Where to go: Enter on Quincy Street; enter on Prescott Street in inclement weather. Accessibility accommodations: Email…

Harpoon Octoberfest Oct 02

The beer is cold, the pretzels are warm, and Octoberfest is back for two very different days of celebrating. FRIDAY, OCTOBER 2 • OCTOBERFEST AFTER DARK Same fest. Different glow. Octoberfest gets a glow up. We’re turning…

Smashing Pumpkins Oct 02
  • TD Garden

Boston, get ready—Smashing Pumpkins are taking over TD Garden for a night that feels like a hometown tradition for live music lovers. Smashing Pumpkins - Boston Boston lands in Massachusetts with the kind of energy that…

Making Strides Against Breast Cancer Walk Oct 03
  • DCR Hatch SHell

Join the Channel 7 Foundation & American Cancer Society Making Strides Against Breast Cancer walk on Saturday, October 3. This fun event will bring together more than 15,000 members of the Greater Boston community…

SpicetoberFest Oct 03
  • City Hall Plaza

Boston’s 2nd SpicetoberFest, a fall spicy harvest festival, is back at City Hall Plaza on October 3, 2026. 11am - 6pm. SpicetoberFest is Boston’s ultimate celebration of spice, flavor, and culture — featuring fiery local…

HONK! Festival 2026 Oct 09
  • Davis Square, Somerville

An awesome annual 3-day free festival bringing brass bands from all over the United States and the world to Somerville for a celebration of music, community and activism. Organized entirely by volunteers and now in its…

East Boston Italian Heritage Parade Oct 11
  • East Boston

The East Boston Italian Heritage Parade is endeavoring to revive a nearly century-long tradition of producing a community-based parade in East Boston's once historically Italian American Community. Despite it's current…

Akaash Singh Oct 16

Akaash Singh is a powerhouse in the comedy scene, captivating audiences nationwide as a stand-up comedian, podcaster, and actor. He first made waves with standout appearances on MTV’s Guy Code and Wild’n Out, Netflix’s…

The Head Of The Charles Regatta Oct 16
  • Charles River, Cambridge

The Head Of The Charles Regatta isn’t just the largest rowing event in the world, it’s Boston’s second-largest sporting event and a powerful celebration of our sport, our city, and our global community. Each October…

Boston Book Festival 2026 Oct 17
  • Copley Square

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…

Sweater Weather Fest: Where Fall Meets Film Oct 17
  • Boston City Hall Plaza

Sweater Weather Fest is a free, all ages event on City Hall Plaza hosted by Sweater Weather Films, where Boston’s film industry opens up to the public. Taking place October 17, the day includes panels with local working…

Affordable Art Fair Oct 22

Affordable Art Fair Boston will return in 2026, showcasing original contemporary artworks ranging from $100 to $10,000. Welcoming a whole host of local, national and international galleries, our first edition is set to…

PruBoo 2026 Oct 25

Join us for a spooktacular day of fun at our 32nd annual PruBoo event! Prudential Center will host our much-anticipated Halloween festivities on Sunday, October 25th from 11:00 AM – 1:00 PM. Parents, bring your…

Can't Miss Activities

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