Annual Events

Stockbridge Chamber of Commerce Events

Stockbridge Main Street at Christmas Weekend  
Saturday-Sunday, December 5 & 6, 2026

Stockbridge Chamber Summer Arts and Crafts Show 
August 15 & 16, 2026, 48 & 50 Main Street, Stockbridge, MA

Halloween Parade & Party 2026
October 30, 2026 6pm – Marchers will meet at the corner of Main & Pine Street at 6:00PM and march up Main Street to the front lawn of the Stockbridge Library for cider & donuts and pumpkin walk-about with lighted pumpkins carved by local businesses and area children. A Halloween storytime will take place at 6:30PM and Drop-in Halloween crafts inside the library from 6:00-7:30PM. Children and businesses interested in showcasing a Jack O’Lantern of their own, should drop them off at the library any time before 5:30PM (The library staff will light them and provide candles).  You may take them home at the end of the evening. In case of rain the parade is cancelled.  Events will continue in the library.

Other Chamber Membership Events 2026

Annual Meeting & Member Celebration, February 18, 2026 5-7PM | The Berkshire Botanical Garden, 5 West Stockbridge Rd, Stockbridge, MA
Please join us for a gathering of chamber members as we review our 2025 year, look towards the future, elect officers and have a conversation among members. This years honoree is Lee Bank.

Spring Tri-town Chamber Mixer hosted by the Lee Chamber of Commerce
Date & Location TBD, MA, 5:00-7:00pm, Network with members of the Lee, Lenox and Stockbridge Chamber’s of Commerce. Light Fare & Cash Bar.  Open Free to Chamber members and their employees

Fall Chamber Mixer
Date & Location TBD, 5:00-7:00pm, Network with members of the Stockbridge Chamber of Commerce. Light Fare & Cash Bar. Open Free to Chamber members and their employees.