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: printern@whdh.com
October Events
Salem Haunted House Grand Parade
Date: October 1st, 2026
Time: 6:30pm
Location : Prime Group Shetland Park to Salem Common Salem, MA 01970
Link : https://www.meetboston.com/event/salem-haunted-happenings-grand-parade/92868/
The Salem Chamber of Commerce invites the community to join the Haunted Happenings Grand Parade on Thursday, October 1, 2026, celebrating this year’s “Old-School Halloween” theme. The parade will follow its traditional route from Prime Group Shetland Park to Salem Common and will officially kick off the Halloween season with music, colorful costumes, and community spirit. Costumes are highly encouraged for all ages!
Sommerville Connection Expo
Date: October 4th, 2026
Time: 10:00am-2:00pm
Location : Arts at the Armory, 191 Highland Ave #1c, Somerville
Link : https://linktr.ee/somervilleconnectionexpo
A Connection Expo is a simple way to connect people with the groups, organizations, and activities that make a community thrive. By bringing many organizations together in one place, a Connection Expo makes it easy for people to discover opportunities, meet organizers, ask questions, and even try activities. Instead of searching online or attending event after event, attendees can explore everything at once. More than an event, a Club Fair is an invitation to participate. It helps people find their place while strengthening the connections that make communities more vibrant, engaged, and resilient.
Kendall Square Farmers Market
Date: October 8th, 2026
Time: 12:00pm-6:00pm
Location : Henri A. Termeer Square , 675 W Kendall St , Cambridge, MA 02142
Link : https://www.massfarmersmarkets.org/kendall
Modeled after the Community Supported Agriculture (CSA) system, the Kendall Square Farmers Market and BioMed Realty partner to provide SNAP recipients with an easy and affordable way to enjoy the market each week through a SNAP-subsidized CSA Market Box. Launched in 2024, the Market Box features seasonal produce from Crimson and Clover Farm, a protein of your choice from Stillman’s Quality Meat or Cape Ann Fresh Catch, mushrooms from My County Mushrooms, and rotating specialty items such as honey, bread, coffee, and chocolate. By sourcing locally, the Market Box offers fresh, seasonal food while supporting farmers and food producers in the region. Located in Kendall Square’s Canal District, the market is a short walk from the Kendall/MIT T station and offers convenient access from the scenic Kendall Canal, creating a welcoming space to explore, connect, and support our local food system.
HONK! Festival 2026
Date: October 9th-11th, 2026
Time: Friday 4:00pm-9:00pm, Saturday 1-9, Sunday 12-2
Location : Davis Square, Somerville Boston, MA 02143
Link : https://honkfest.org/2026-festival/schedule-2026/
HONK! is a free, three-day street music festival in Somerville featuring brass bands from around the world. The festival includes parades, live music, dancing, and community events, with more than 30 bands taking over Davis Square and the streets between Somerville and Harvard Square. It celebrates music, creativity, community, and activism in a fun, energetic, and welcoming atmosphere.
The Head of the Charles Regatta
Date: October 16th-18th, 2026
Time: 8:00am-5:00pm
Location: Charles River Reservation , Boston/Cambridge, MA
Link: https://www.hocr.org/
The Head of the Charles Regatta is one of the world’s largest rowing events and a major Boston tradition, bringing together more than 11,750 athletes and 325,000 spectators each October. Now in its 61st year, the three-mile race winds through Boston and Cambridge along the Charles River, passing Harvard, MIT, and BU and featuring seven historic bridges and challenging turns. Taking place October 16–18, 2026, the regatta celebrates rowing, community, and athletes of all ages and abilities from around the world.
Open Streets Boston
Date: October 18th, 2026
Time: 10:30am-3:30pm
Location: Roslindale Square from Belgrade Ave. to Washington St.
Link:https://www.boston.gov/departments/transportation/open-streets-boston
Open Streets Boston returns in 2026 with free, car-free neighborhood events for the whole community. Enjoy music, games, biking, local businesses, and more in pedestrian-friendly streets. Events run 10:30 AM–3 PM. Streets close to vehicles at 9 AM and reopen at 4 PM. Parking is prohibited along the route from 6 AM–4 PM.
Greenway Artisan Market
Date: October 24th-25th, 2026
Time: 11:00am-5:00pm
Location: Rose Kennedy Greenway
Boston, MA
Link: https://www.greenwayartisanmarket.com/
Explore a vibrant open-air market along Boston’s Waterfront at the Rose Kennedy Greenway, featuring 50+ local artists, makers, designers, and small businesses. Browse unique art, handmade goods, jewelry, clothing, food, and more from local vendors.
Boston Book Festival 2026
Date: October 17th, 2026
Time: 10:00am-5:00pm
Location: Copley Square, 10 Guest Street, Suite 220 Boston, MA 02135
Link: https://bostonbookfest.org/
The Boston Book Festival celebrates the power of books and ideas through year-round events and an annual festival that brings readers, writers, and the community together. Featuring a diverse lineup of acclaimed authors and speakers, the festival promotes a love of reading, encourages meaningful conversations, and celebrates Boston’s vibrant literary community.
Sweater Weather Fest
Date: October 17th, 2026
Time: 2:00pm-11:00pm
Location: Boston City Hall Plaza , 1 City Hall Square . Boston, MA 02201-2006
Link: https://www.boston.gov/calendar/sweater-weather-fest
Sweater Weather Fest is a free, all-ages celebration of Boston’s film community taking place October 17 at City Hall Plaza. The event features panels with local filmmakers and production companies, a short film contest, seasonal vendors, local food, and a beer garden. The day wraps up with an outdoor feature film screening, offering a fun way to enjoy fall while connecting with Boston’s local film industry.
SoWa Vintage Market
Date: October 25th, 2026
Time: 11:00am-4:00pm
Location: SoWa Boston, 450 Harrison Ave , Boston, MA 02118
Link: https://www.sowaboston.com/sowa-vintage-market
Located downstairs at 450 Harrison Ave, the SoWa Vintage Market is Boston’s weekly destination for antiques, collectibles, vintage goods, and other one-of-a-kind curiosities. The Vintage Market is open every Sunday year round, rain or shine.