Festivals in Lenox, MA
Looking for festivals events or things to do in Lenox, MA? Historic downtown streets and expansive parklands transform regularly into lively open-air gathering spaces for community celebrations. Visitors and locals typically start by exploring downtown village plazas or historic estate grounds where seasonal gatherings bring people together.
- Through the walkable downtown historic village, visitors find lively artisan markets and seasonal celebrations like the annual Apple Squeeze taking over local plazas.
- Expansive historic estate grounds host major cultural gatherings, providing open-air lawn seating and immersive seasonal programs.
- Intimate community parks offer relaxed evening music series and family-friendly outdoor gatherings during peak warmer months.
All-inclusive Christmas by Candlelight Getaway | Bus, Admission & Dining
Sat, Dec 12, 4:30 PM
Sturbridge · Old Sturbridge Village
All-inclusive Christmas by Candlelight Getaway | Bus, Admission & Dining
Sat, Dec 12, 4:30 PM
Sturbridge · Old Sturbridge Village
Winter Wonderland Pizza With Santa At The Learning Experience Southington
Sat, Dec 19, 11:00 AM
Southington · The Learning Experience
Winter Wonderland Pizza With Santa At The Learning Experience Southington
Sat, Dec 19, 11:00 AM
Southington · The Learning Experience
2027 Hudson Valley Wine & Food Festival
Sat, Sep 11, 11:00 AM
Rhinebeck · Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA
2027 Hudson Valley Wine & Food Festival
Sat, Sep 11, 11:00 AM
Rhinebeck · Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA
Stew Leonard's Danbury 32nd Annual Christmas Tree Lighting Celebration
Thu, Dec 3, 4:30 PM
Danbury · Stew Leonard's
Stew Leonard's Danbury 32nd Annual Christmas Tree Lighting Celebration
Thu, Dec 3, 4:30 PM
Danbury · Stew Leonard's
Diwali - Festival of Lights- A sizzling variety Entertainment Program
Saturday at 3:30 PM
Stamford · Westover Magnet Elementary School
Diwali - Festival of Lights- A sizzling variety Entertainment Program
Saturday at 3:30 PM
Stamford · Westover Magnet Elementary School

2026 New Britain Holiday Makers Market New Britain, CT
Sat, Nov 21, 10:00 AM
New Britain · New Britain Museum of American Art

2026 New Britain Holiday Makers Market New Britain, CT
Sat, Nov 21, 10:00 AM
New Britain · New Britain Museum of American Art
VINYL FUN! The Plainville Record Riot! Sunday December 6th 9:30 AM-3:30 PM
Sun, Dec 6, 9:30 AM
Plainville · Veterans of Foreign Wars
VINYL FUN! The Plainville Record Riot! Sunday December 6th 9:30 AM-3:30 PM
Sun, Dec 6, 9:30 AM
Plainville · Veterans of Foreign Wars
Frequently asked questions about Lenox
