Jenna Levin October 3, 2025
Fall in New England is one of the most beautiful times of year—and the Boston area is packed with events, community happenings, and local updates. Whether you’re in the mood for live music, family fun, or want to stay in the loop on neighborhood news, here’s your October guide!
Oct 1–5 | Charles River, Cambridge
One of the largest rowing events in the world—catch breathtaking fall views along the river while cheering on the rowers.
Oct 11 | Boston Common Frog Pond
Perfect for families! Pumpkin bowling, haunted mazes, and glowing fun for kids of all ages.
Hamilton – Boston Opera House (Oct 1–Nov 2)
Rocky Horror Picture Show (Oct 1)
Rodgers & Hammerstein’s Cinderella (Oct 2)
Kevin Bridges, Comedy Night (Oct 8)
Big Apple Circus (Oct 9–Nov 2)
Chance The Rapper – Oct 4
Yusuf Islam / Cat Stevens – Oct 6
Jesse McCartney – Oct 7
Maná – Oct 10
Gipsy Kings – Oct 14
Downtown Boston Arts Market
Freedom Trail History & Brewery Tours
SpicetoberFest Food Festival
Ghosts & Gravestones Haunted Trolley Tour
Fall Foliage Cruises
Needham Harvest Fair – Oct 5, 11 AM–3 PM at Greene’s Field
Needham Farmers Market – Sundays, 11 AM–3 PM at Town Hall
Elizabeth Seton Residence Casino Night – Fundraiser
Walk to End Alzheimer’s – Greater Boston (morning event)
Climate Action Event – Oct 1, 12–1:30 PM
Wellesley Night at Babson College – Evening in October
Wellesley College Art Exhibits & Sound Lounge Sessions – Ongoing
National Chamber Orchestra of Armenia – Oct 5, 6 PM
Tiya Miles: Eco-Consciousness Talk – Oct 8, 7 PM
Inner Circle Boston Social – Oct 9, 6 PM
Musical Bingo & Acoustic Open Mic – Early October
Newtonville Village Day Registration Deadline – Oct 12
Enjoy all that October in New England has to offer! And as always, if you’d like recommendations on neighborhoods, dining, or homes in the Boston suburbs, I’d love to connect.
Stay up to date on the latest real estate trends.
Why Wellesley Is a Luxury Real Estate Hub
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