Halloween Happenings in The Berkshires

When foliage season ends, Halloween becomes the star of the show - Berkshire County’s unique combination of ghostly history, creative cultural institutions, and sprawling Victorian estates lends itself to the festivities, so there is plenty to do! Here are a few of our favorite October activities:

Stockbridge’s historic home Naumkeag is the hub of Halloween fun in The Berkshires. The Incredible Naumkeag Pumpkin Show is incredible, as advertised – More than 1000 pumpkins and gourds adorn the spectacular gardens, along with hundreds of creepy and funny jack-o-lanterns. The Pumpkin Trail allows children to meander through Naumkeag’s pumpkin-lit property, learning about local critters as they explore. The Halloween fun at Naumkeag doesn’t stop there – they also offer one of the county’s best haunted houses, a mind-reading mentalist, and a group séance – plus all-ages trick-or-treating on Halloween Night!

Another historic property, Hancock Shaker Village, hosts Haunted Hancock every Thursday in October. This spine-chilling, after-hours tour includes true tales of ghostly sightings and discussions of the Shakers’ role in the spiritualist movement. Then, on October 26th, put on your costume for some daytime trick-or-treating during Halloween at Hancock, with ghost stories, fortune telling and more!

The Norman Rockwell Museum gets in on the Halloween fun with a guided tour of Stockbridge Cemetery on October 24th. Museum educators Tom Daly and Mary Berle lead this informative tour that includes the burial site of Rockwell himself, and provides wonderful and dark details about the history of Stockbridge.

Whitney’s Farm is a great place to bring your kids this Halloween season! The farm’s Pumpkin Fest, Haunted Corn Maze, and hayrides make it a perfect destination for fall family fun.

This year marks Pittsfield’s 10th annual Zombie Pub Crawl on Saturday, October 12th. The 21+ event includes stops at 10 great bars, beginning at 5pm. This FREE event includes a makeup station, in case you need some assistance with your costume!

Edith Wharton’s former home, The Mount, offers Friday Night Frights throughout the month – come for a two-hour ghost tour that highlights the most haunted parts of the Gilded Age mansion, and learn about eerie, unexplainable occurrences at the historic property.

IS183, our local art school, is hosting an all-ages trick-or-treat trivia on Halloween night at Pittsfield’s Colonial Theatre. It’s a great way to test your trivia knowledge, with cash prizes for the winners! Trivia will be followed by a costume contest at 8:30pm, so make sure you’re decked out and ready to compete.

October is known as foliage season in Berkshire County, but there is so much more to see and do. Come to The Berkshires for the most Spooktacular October of your life!