Boston, October 9, 2025
News Summary
October in Boston is bustling with a variety of cultural and community events. From the HONK! Festival of Activist Street Bands to the Head Of The Charles Regatta, the city is alive with performances, competitions, and family activities. Families can enjoy Fall Fest at Rose Kennedy Greenway, the Boston Book Festival, and Halloween-themed events while experiencing the rich tapestry of music, art, and community celebration throughout the month.
Boston. October in Boston brings a packed calendar of cultural, community and fall-themed events, led by major outdoor festivals, family activities and signature sporting competitions. The month features the HONK! Festival of Activist Street Bands, the Head Of The Charles Regatta, neighborhood fall celebrations on the Rose Kennedy Greenway, screenings and movie nights, and a variety of performances, fairs and community marches that aim to showcase local and visiting artists, performers and organizations.
Key events and dates
The HONK! Festival will take place from October 9-12 with various events including live performances, workshops, and a parade.
The Head Of The Charles Regatta, the world’s largest rowing competition, is set for October 17-19 on the Charles River.
PruBoo, an annual trick-or-treat event benefiting Boston Children’s Hospital, is scheduled for October 26th at the Shops at Prudential Center.
The Boston Book Festival, featuring discussions with various authors, will culminate on October 25th with a street fair and live music.
Music, street performance and parades
Stock Photo Boston is a colorful tapestry of music, laughter, and the beauty of fall.
The HONK! Festival of Activist Street Bands celebrates creativity and community with music rooted in activism.
The festival will transform Somerville, Cambridge, and adjacent neighborhoods into a living stage with no amplification or stages, featuring bands with styles from Klezmer, Afrobeat, punk, samba, and second line.
Fiesta En La Plaza and Fortune Feimster’s “Takin’ Care of Biscuits” tour are part of the vibrant cultural offerings this October.
Family activities, parks and fall celebrations
Rose Kennedy Greenway will host free activities including Fall Fest on October 3rd, featuring food trucks, artisan vendors, and family-friendly entertainment.
Greenway Fall Movie Nights will screen films on various dates throughout October, including “The Addams Family” and “Halloweentown,” with free popcorn available.
Howl-O-Ween, a pet costume contest, will occur on October 18th at Peter’s Park Dog Park.
The Great Bridal Expo will be held on October 26th, showcasing wedding-related vendors and services.
Arts, film and museums
A screening of “Hocus Pocus” will be held at The Anchor on October 15th during its Watch Wednesdays movie series.
Museums in Boston will offer free admission on October 13th in honor of Indigenous American peoples.
The MassQ Ball 2025: Color event on October 4th is a celebration of ritual, performance, and cross-cultural arts at Arnold Arboretum.
Wicked Comic Con will take place on October 5th, showcasing comic books, creators, and cosplay.
Community observances and cultural festivals
The Indigenous Peoples’ Day March will honor heritage and acknowledges the histories and cultures of Indigenous American peoples.
Downtown Diwali will be celebrated on October 11th at Faneuil Hall with crafts and performances reflecting the cultural significance of the festival.
Performances and comedy
Erica Rhodes, known for her run on “America’s Got Talent” in 2024, will perform her stand-up comedy at the city.
Outdoor excursions and seasonal highlights
Boston’s Fall Foliage Cruise offers a 90-minute scenic journey along the Charles River, showcasing colorful autumn views and the skylines of Boston and Cambridge.
Summary
Events this October in Boston celebrate culture, community, and creativity, ensuring a lively atmosphere throughout the month.
Practical information
Most events are held at public parks, neighborhood streets and established venues across greater Boston, including Somerville, Cambridge, the Rose Kennedy Greenway, Faneuil Hall, the Arnold Arboretum, the Charles River and major indoor event spaces. Dates, times and specific locations vary by event; some activities are free while others may require tickets or registration.
FAQ
What are the dates and highlights for the HONK! Festival?
The HONK! Festival will take place from October 9-12 with various events including live performances, workshops, and a parade.
When is the Head Of The Charles Regatta?
The Head Of The Charles Regatta, the world’s largest rowing competition, is set for October 17-19 on the Charles River.
When and where is PruBoo?
PruBoo, an annual trick-or-treat event benefiting Boston Children’s Hospital, is scheduled for October 26th at the Shops at Prudential Center.
What happens at the Rose Kennedy Greenway in October?
Rose Kennedy Greenway will host free activities including Fall Fest on October 3rd, featuring food trucks, artisan vendors, and family-friendly entertainment.
Are there special museum days in October?
Museums in Boston will offer free admission on October 13th in honor of Indigenous American peoples.
What family-friendly movie screenings are scheduled on the Greenway?
Greenway Fall Movie Nights will screen films on various dates throughout October, including “The Addams Family” and “Halloweentown,” with free popcorn available.
What is the Boston Book Festival schedule?
The Boston Book Festival, featuring discussions with various authors, will culminate on October 25th with a street fair and live music.
What special observances occur in October?
The Indigenous Peoples’ Day March will honor heritage and acknowledges the histories and cultures of Indigenous American peoples.
Are there fall cruises available?
Boston’s Fall Foliage Cruise offers a 90-minute scenic journey along the Charles River, showcasing colorful autumn views and the skylines of Boston and Cambridge.
Which comic and pop culture event is in October?
Wicked Comic Con will take place on October 5th, showcasing comic books, creators, and cosplay.
Event schedule table
| Event | Date(s) | Location | Notes |
|---|---|---|---|
| HONK! Festival | October 9-12 | Somerville, Cambridge and adjacent neighborhoods | Live performances, workshops, parade; no amplification or stages for many performances |
| Head Of The Charles Regatta | October 17-19 | Charles River | World’s largest rowing competition |
| Rose Kennedy Greenway Fall Fest | October 3 | Rose Kennedy Greenway | Free activities, food trucks, artisan vendors, family entertainment |
| Greenway Fall Movie Nights | Various dates in October | Rose Kennedy Greenway | Includes “The Addams Family” and “Halloweentown”; free popcorn |
| Boston’s Fall Foliage Cruise | October (select dates) | Charles River | 90-minute scenic journey showcasing seasonal colors and skylines |
| Museums free admission day | October 13 | Museums in Boston | Free admission in honor of Indigenous American peoples |
| PruBoo | October 26 | Shops at Prudential Center | Trick-or-treat for Boston Children’s Hospital |
| Boston Book Festival | October 25 | Downtown/streets | Author discussions, street fair, live music |
| MassQ Ball 2025: Color | October 4 | Arnold Arboretum | Ritual, performance and cross-cultural arts |
| Wicked Comic Con | October 5 | Venue in Boston | Comic books, creators and cosplay |
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Additional Resources
- Boston.com: 10 Free Things to Do in Boston in October
- Boston Globe: Free Things to Do in Boston
- Mommy Poppins: Best Halloween Events in Boston
- Wikipedia: Boston
- Jewish Boston: Yom Kippur at The Fairmont Copley Hotel
- Google Search: Boston Events October 2025
Author: STAFF HERE BOSTON WRITER
BOSTON STAFF WRITER The BOSTON STAFF WRITER represents the experienced team at HEREBoston.com, your go-to source for actionable local news and information in Boston, Suffolk County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as Boston Marathon, Head of the Charles Regatta, and Boston Harborfest. Our coverage extends to key organizations like the Greater Boston Chamber of Commerce and Associated Industries of Massachusetts, plus leading businesses in finance, biotech, and insurance that power the local economy such as Fidelity Investments, Biogen, and Liberty Mutual Insurance. As part of the broader HERE network, we provide comprehensive, credible insights into Massachusetts's dynamic landscape.
