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
Back to Top of List- Franklin Park Zoo
- Recurring daily
Boston Lights returns! Prepare to be dazzled as you wander through this glowing immersive experience filled with vibrant lantern displays, interactive activities and Instagrammable moments at every turn. Each year…
- North End Historical Museum
- Recurring weekly on Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday
Boston's oldest neighborhood finally has a museum of its own! Explore, learn, and uncover the rich history that makes the North End unique. Step inside the North End Historical Museum at 3 Prince Street and walk through…
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…
- 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…
- Citizens Opera House
- Recurring weekly on Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday
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
- Recurring monthly on the last Thursday
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…
- Boston Symphony Orchestra / Boston Pops / Symphony Hall
- Recurring daily
The scintillatingly expressive Korean pianist Seong-Jin Cho rose to stardom after winning First Prize at the Chopin International Competition at age 20. A frequent collaborator of Andris Nelsons and the BSO, he returns…
- Chelsea High School
Boston Landmarks Orchestra, led by Music Director Christopher Wilkins, will present a free community concert, “A Celebration of National Hispanic Heritage Month,” on Friday, October 2 at 7:00pm at Chelsea High School…
- Harpoon Brewery
- Recurring daily
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…
- 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…
- 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…
- 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…
The Boston Bruins take on the Ottawa Senators at TD Garden!
Embark on a 90 minute scenic cruise along the Charles River, where you’ll have the opportunity to admire the stunning foliage along the Esplanade and take in the picturesque views of both Boston and Cambridge. Tour…
- 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…
Experience the official “Outlander” in-concert event! A live orchestra performs Bear McCreary’s acclaimed score, curated by showrunner Matthew B. Roberts, while highlights from eight seasons illuminate the screen. From…
- 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…
Join us to celebrate Indigenous Peoples’ Day at the MFA with free admission for all Massachusetts residents. Enjoy gallery tours, engaging family art-making activities, and more! Indigenous Peoples’ Day recognizes and…
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…
- 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…
- 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…
- 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…
- SoWa Power Station
- Recurring daily
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…
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…
Every year, something unexpected happens behind these historic walls. This Halloween, The Liberty steps into the space between virtue and vice. On Saturday, October 31st, Sinners & Saints takes over The Liberty for a…
Can't Miss Activities
Back to Top of ListBoston Fall Bucket List
We've gathered the ultimate fall bucket list for every visitor and local to tackle.
Oktoberfest Celebrations
It's beer season in Boston - discover where to raise a stein this year.
Columbus Day / Indigenous Peoples' Day
Discover how to spend the perfect long weekend in Boston.
Head of the Charles Regatta
Boston’s world-famous rowing event returns to the scenic Charles River.
Halloween in Boston
From ghost tours to pumpkin patches, there’s something for every ghoul and goblin.
Fall Festivals in Boston
Pair sweater weather with the perfect outdoor festival.
Plan Your Getaway
Back to Top of ListHotel Packages in Boston
Elevate your trip to Boston with these hotel packages.
Plan A Trip to Boston
The city for history buffs, music lovers, sports fanatics, foodies, and, truthfully, everyone!
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