Guides › Halloween

Halloween events in Great Barrington

If you only go out for one thing this fall, make it Halloween in Great Barrington. The haunted attractions, corn mazes, and pumpkin patches below are the real lineup — check back, because dates land through October.

Annual traditions — dates TBA

These happen every year; exact dates are announced closer to the day.

Fairview Hospital Monster Dash 5K

Dates TBA (Sat Oct 24, 2026; Halloween-themed charity 5K in Great Barrington) · Fairview Hospital - Monster Dash 5K More info

Great Barrington Downtown Trick-or-Treat

Dates TBA (Halloween evening, Oct 31; Berkshire listings give Great Barrington trick-or-treat hours of 5:30-7:30pm, and downtown businesses join the annual Downtown Trick-or-Treat celebration) · Great Barrington Downtown Trick-or-Treat · Free More info

Housatonic Halloween Parade & Costume Contest

Dates TBA (Sat Oct 31, 2026 in Housatonic Village: Halloween parade, costume contest and family activities during town trick-or-treat hours 5:00-7:00pm (road closure 3:30-7:30pm); parade from Ramsdell to the Housy Dome and the Commons) · Housatonic Village Halloween Parade & Costume Contest More info

If you book through these links, Dayfari may earn a commission at no extra cost to you.

Good to know

Haunted houses sell out on the last two weekends — book ahead, don't walk up.
Pumpkin patches are best on weekday mornings: smaller crowds, better light for photos.
Bring cash for the farm stands; card readers and corn mazes don't always mix.
Check age guidance before bringing small kids to a haunt — 'family fright nights' are the gentler pick.

More in Great Barrington

Open the Dayfari app for this weekend's events.
More things to do in Great Barrington