Boston, September 30, 2025
News Summary
Boston’s Rose Kennedy Greenway will feature a weekend filled with family-friendly activities, including a Fall Fest on October 3 and the start of Greenway Fall Movie Nights. Residents and visitors can enjoy food trucks, artisan vendors, and community art events throughout October. Numerous events celebrating arts, culture, and outdoor activities will take place across the city, making it a vibrant time for families and individuals alike.
Boston — Boston’s Rose Kennedy Greenway is featuring free fall activities, with a weekend of family-oriented events, outdoor film screenings, arts programming and community gatherings scheduled across the city throughout October.
What’s happening now and next (quick summary)
The Greenway will host Fall Fest on Oct. 3 and launch its Greenway Fall Movie Nights the same evening. A range of other October events across Boston includes arts celebrations, conventions, museum access days, a major rowing regatta, literary programming, pet-focused activities and seasonal offerings such as apple picking and haunted attractions in Massachusetts.
Lead events and most important details
Fall Fest and Greenway movie series
Fall Fest will take place on Oct. 3 from 4:30 to 8:30 p.m. at Rowes Wharf Plaza. Fall Fest includes food trucks, artisan vendors, music by DJ JayVibez, glow mini golf, inflatable obstacle course, face painting, crafts, and pumpkin decorating.
Greenway Fall Movie Nights will start on Oct. 3 at 6:30 p.m. with “The Addams Family” (1991). Other scheduled movies include “Goosebumps” on Oct. 10, “Twilight” on Oct. 17, and “Halloweentown” on Oct. 24. Free popcorn and candy will be available while supplies last during movie screenings. Exclusive Greenway blankets can be rented for free during the film with a valid ID or credit card.
Major cultural and community events
The MassQ Ball 2025: Color event celebrating cross-cultural arts and the MassQing art practice will be held on Oct. 4 from 10 a.m. to 4 p.m. at the Arnold Arboretum.
Wicked Comic Con will occur on Oct. 5 from 10 a.m. to 5 p.m. at the Westin Boston Seaport District, featuring comic book vendors and artwork.
Free access to museums in Boston to honor Indigenous American peoples will be available on Oct. 13, including the Museum of Fine Arts and the Institute of Contemporary Art.
“Hocus Pocus” screening on Oct. 15 at 9 p.m. at The Anchor as part of its Watch Wednesdays movie series.
Sports, pets and family dates to note
The Head Of The Charles Regatta, a major rowing competition, will take place from Oct. 17-19 on the Charles River.
Howl-O-Ween pet costume contest and parade will be held on Oct. 18 from 9 a.m. to 1 p.m. at Peter’s Park Dog Park.
The Boston Book Festival will celebrate literature on Oct. 25 from 10 a.m. to 6 p.m. at Copley Square, featuring multiple author discussions.
The Great Bridal Expo will showcase wedding vendors on Oct. 26 from noon to 4 p.m. at the Westin Boston Seaport District.
PruBoo trick-or-treat event benefiting Boston Children’s Hospital will take place on Oct. 26 from 11 a.m. to 1 p.m. at the Prudential Center, with a $5 donation per child for a trick-or-treat bag.
Additional seasonal offerings and opportunities
Additional seasonal offerings include the Moonwalkers: A Journey with Tom Hanks and Candlelight Concerts throughout the month. Opportunities for apple picking and other fall activities such as visiting haunted attractions in Massachusetts are highlighted for seasonal enjoyment.
Practical information and accessibility
Many Greenway events and movie nights are free to attend. Some items at events may be provided while supplies last, such as free popcorn and candy during movie screenings. Exclusive Greenway blankets can be rented for free during the film with a valid ID or credit card. The PruBoo trick-or-treat event requests a $5 donation per child for a trick-or-treat bag to benefit Boston Children’s Hospital. Specific event times and locations are listed above; visitors should plan arrival and transportation according to the schedules for each site.
Background and context
Boston’s October calendar regularly combines outdoor and indoor programming to reflect seasonal interest in family activities, arts and sports. The Rose Kennedy Greenway serves as a central public space for fall gatherings and free entertainment, while institutions across the city open programming for cultural observance and community engagement. Annual sporting events, such as the Head Of The Charles Regatta, draw regional and international participants and spectators, and seasonal attractions extend into nearby Massachusetts locations for apple picking and themed attractions.
How to use this information
Refer to the event list above for dates, times and locations. Arrive early for high-demand activities such as the Head Of The Charles Regatta and major film screenings. Confirm any specific access requirements or registration details directly with event organizers where noted, especially for items that require IDs or donations.
FAQ
What is happening on the Greenway?
Boston’s Rose Kennedy Greenway is featuring free fall activities.
When and where is Fall Fest?
Fall Fest will take place on Oct. 3 from 4:30 to 8:30 p.m. at Rowes Wharf Plaza.
What is included in Fall Fest?
Fall Fest includes food trucks, artisan vendors, music by DJ JayVibez, glow mini golf, inflatable obstacle course, face painting, crafts, and pumpkin decorating.
When do Greenway Fall Movie Nights start and what will be shown?
Greenway Fall Movie Nights will start on Oct. 3 at 6:30 p.m. with “The Addams Family” (1991).
What other movies are scheduled for Greenway Fall Movie Nights?
Other scheduled movies include “Goosebumps” on Oct. 10, “Twilight” on Oct. 17, and “Halloweentown” on Oct. 24.
Will there be concessions at the movie screenings?
Free popcorn and candy will be available while supplies last during movie screenings.
Are there blanket rentals for the Greenway films?
Exclusive Greenway blankets can be rented for free during the film with a valid ID or credit card.
When and where is the MassQ Ball 2025: Color event?
The MassQ Ball 2025: Color event celebrating cross-cultural arts and the MassQing art practice will be held on Oct. 4 from 10 a.m. to 4 p.m. at the Arnold Arboretum.
When and where is Wicked Comic Con?
Wicked Comic Con will occur on Oct. 5 from 10 a.m. to 5 p.m. at the Westin Boston Seaport District, featuring comic book vendors and artwork.
When will museums offer free access to honor Indigenous American peoples?
Free access to museums in Boston to honor Indigenous American peoples will be available on Oct. 13, including the Museum of Fine Arts and the Institute of Contemporary Art.
Are there other notable screenings and dates?
“Hocus Pocus” screening on Oct. 15 at 9 p.m. at The Anchor as part of its Watch Wednesdays movie series.
When is the Head Of The Charles Regatta?
The Head Of The Charles Regatta, a major rowing competition, will take place from Oct. 17-19 on the Charles River.
When is the Howl-O-Ween pet costume contest and parade?
Howl-O-Ween pet costume contest and parade will be held on Oct. 18 from 9 a.m. to 1 p.m. at Peter’s Park Dog Park.
What is the schedule for the Boston Book Festival?
The Boston Book Festival will celebrate literature on Oct. 25 from 10 a.m. to 6 p.m. at Copley Square, featuring multiple author discussions.
When is the Great Bridal Expo and PruBoo?
The Great Bridal Expo will showcase wedding vendors on Oct. 26 from noon to 4 p.m. at the Westin Boston Seaport District. PruBoo trick-or-treat event benefiting Boston Children’s Hospital will take place on Oct. 26 from 11 a.m. to 1 p.m. at the Prudential Center, with a $5 donation per child for a trick-or-treat bag.
Are there other seasonal activities mentioned?
Additional seasonal offerings include the Moonwalkers: A Journey with Tom Hanks and Candlelight Concerts throughout the month. Opportunities for apple picking and other fall activities such as visiting haunted attractions in Massachusetts are highlighted for seasonal enjoyment.
Quick reference table
| Date | Event | Time | Location | Cost / Notes |
|---|---|---|---|---|
| Oct. 3 | Fall Fest | 4:30–8:30 p.m. | Rowes Wharf Plaza | Free entry; activities include food trucks and vendors |
| Oct. 3–Oct. 24 (Wednesdays) | Greenway Fall Movie Nights | 6:30 p.m. start times | Greenway (Rowes Wharf Plaza) | Free popcorn and candy while supplies last; Exclusive Greenway blankets can be rented for free during the film with a valid ID or credit card |
| Oct. 4 | MassQ Ball 2025: Color | 10 a.m.–4 p.m. | Arnold Arboretum | Celebrates cross-cultural arts and the MassQing art practice |
| Oct. 5 | Wicked Comic Con | 10 a.m.–5 p.m. | Westin Boston Seaport District | Comic book vendors and artwork |
| Oct. 13 | Free museum access | Varies by museum | Museum of Fine Arts; Institute of Contemporary Art | Free access to museums in Boston to honor Indigenous American peoples |
| Oct. 15 | “Hocus Pocus” screening | 9 p.m. | The Anchor | Part of Watch Wednesdays movie series |
| Oct. 17–19 | Head Of The Charles Regatta | Varies | Charles River | Major rowing competition |
| Oct. 18 | Howl-O-Ween pet costume contest & parade | 9 a.m.–1 p.m. | Peter’s Park Dog Park | Pet-focused family event |
| Oct. 25 | Boston Book Festival | 10 a.m.–6 p.m. | Copley Square | Multiple author discussions |
| Oct. 26 | Great Bridal Expo; PruBoo | Expo: noon–4 p.m.; PruBoo: 11 a.m.–1 p.m. | Westin Boston Seaport District; Prudential Center | PruBoo trick-or-treat event benefiting Boston Children’s Hospital; $5 donation per child for a trick-or-treat bag |
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Additional Resources
- Boston Uncovered: Things to Do in Boston – October
- Boston.com: Haunted Houses and Halloween Events
- Rock 92.9: Halloween Glassblowing Events
- Modern Luxury: Boston Events in October 2025
- Jewish Boston: Evening of Remembrance & Hope
- Wikipedia: Boston
- Google Search: Boston Events October 2025
- Encyclopedia Britannica: Boston
- Google Scholar: Boston October Events
- Google News: Boston October 2025 Events
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.
