Halloween in Stockbridge, MA

Stockbridge, Massachusetts – Looking for a festive way to celebrate Halloween with your family? Stockbridge offers a few opportunities to scare up some fun and frights for all ages.

About three quarters of a mile from downtown Stockbridge you’ll find Naumkeag, a Trustees of Reservations property and the former country estate of noted New York City lawyer Joseph Hodges Choate, located at 5 Prospect Hill Road. Creep through the woods at night during the annual Pumpkin Trail on October 13 & 14 as 200 carved jack-o-lanterns light your way. Listen for the woodland creatures on the trail who will greet you and regale you with funny and informative stories of their nocturnal activities. Ideal for kids under 12.

Feeling a little more daring? Ready to be frightened in grand Berkshire style? Visit Naumkeag October 20 & 21 and 27 & 28 for their recently resurrected Annual Halloween Haunted House. Be prepared to be scared as you stroll the gardens and tour all three floors of the Gilded Age “cottage” where ghosts and ghoulish creatures await you. Recommended for ages 12+ (parental discretion). You can contact Naumkeag at 413-298-3239 to learn more about house tours and events.

For more traditional fun, the Stockbridge Chamber of Commerce will host the annual Halloween Parade & Party on October 27. Those looking to participate in the parade should gather in costume at Main & Pine Streets prior to 6 p.m. ready to march up Main Street to the Town Offices where cider and donuts will be served. This event is open to area children and their families. In case of rain, all activities will take place at the library.

Immediately following the Halloween Parade, the Stockbridge Library Association will host the 7th Annual Pumpkin Walk-About in the Stockbridge Library gardens. If you are carving a jack-o-lantern, drop it off at the Library between 5:00 & 6:00 p.m. When you come back after the parade the path will be lit by all the pumpkins carved by local businesses, your neighbors, and you! There will also be some spooky stories and a Halloween treat.

Come out and join in the traditions, both old and new in this quintessential New England town!