Find yourself in Stockbridge, MA and discover the best of New England, as the Stockbridge area offers history, celebrity, romance & intrigue. Home to the Norman Rockwell Museum, Tanglewood, Naumkeag, The Berkshire Theatre Group, Chesterwood, Berkshire Botanical Garden, & Stockbridge Main Street at Christmas.

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Stockbridge Main Street at Christmas
December 5 & 6, 2026
We invite antique car owners to be part of this cherished tradition by showcasing their vehicles during Sunday’s recreation. Pre registration required.

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REMINDER NOTICE: The Stockbridge Halloween Parade and Pumpkin Walk will take place on Friday, October 30, 2026 for area children. Marchers will meet at the corner of Main & Pine Street at 6:00 p.m. and march up Main Street to the front lawn of the Stockbridge Library for cider & donuts, and pumpkin walk-about with Jack-O-Lanterns carved by local businesses and area children. The fire truck will be stationed for discovery. A Halloween story time will take place at 6:30PM and Drop-in Halloween crafts inside the library from 6:00-7:30 p.m. Children and businesses interested in showcasing a Jack-O-Lantern of their own, should drop them off at the library any time before 5:30 p.m. (The library staff will light them and provide candles). You can take them home at the end of the evening. In case of rain the parade is canceled, and activities will take place in the library. These events are sponsored by the Stockbridge Chamber of Commerce, Stockbridge Library, Stockbridge Police & Fire Departments, and Trustco Bank.
October is the ideal time to visit this glorious Ventfort Hall Mansion and Gilded Age Museum ! With All Hallows Eve on the brink, they have a little something for everyone below, including a Halloween Light Tea Service, a Saturday Salon Talk on the Art of Cemetery Symbolism, and enthusiastic offerings for Lenox’s October 30th Trunk or Treat -- as well as our ever-popular Ghost Tours with Robert Oakes, and a Paranormal Investigation with David Raby. Start your Lenox Trunk or Treat Tour at Ventfort Hall! They’re staying open later on Friday, October 30 and after 2pm, they’re offering free admission for those who dressed for the occasion! On October 31, Join them for a Halloween Light Tea Service at 12:30pm, and hop across the hall for Louise’s Salon Talk discussing the art and interpretations of Cemetery Symbolism. Open Late Till 7:30pm on October 31 - Free For Anyone in Costume After 2pm - Book Your Admission Ticket Now!
The Incredible Naumkeag Pumpkin Show is offering a special offer to Stockbridge residents on Halloween night. All town residents will receive 50% off admission and kids in costume are welcome free. Use coupon code STOCKBRDIGE when buying tickets for the event at @naumkeagofficial #StockbridgeMA
@naumkeagofficial Pumpkin Show running Wednesday thru Sunday to October 31st! #visitstockbridgema #stockbridgema