Fall Foliage Fun & Halloween Spookiness in the Berkshires

Ongoing

Friday Night Fright – The Mount Ghost Tours
It starts with the sounds—creaking floors and slamming doors, fading footsteps down empty halls—a feeling of being watched, tingling taps on the shoulders, spectral shapes crouched in corners or gathered in front of fireplaces long gone cold. Tricks of the imagination in an old house once inhabited by a skilled writer of ghost stories … or something else? Take a ghost tour and decide for yourself. Not for children under 12. Fridays, 5:45PM & 7PM.  September 6 – October 25.

Housatonic Heritage Walks
A great way to see the beautiful Berkshire foliage with these free guided interpretive heritage walks over 4 weekends, September 7 – September 29.

Ioka Valley Farm
Pumpkin picking, hayrides, mini-corn maze, homemade cider donuts and Pumpkin Whoopie Pies or visit Café-A for a BBQ sandwich and more. Great Fall fun for the entire family! Saturday & Sunday, September 20 – October 27.

Fall Foliage Train Rides
Bring the family and enjoy the colors of the season on this hour-long train ride. Children under 3 free. Departures at 10:30am, 12:30pm, 2:30pm, & 4:30pm. Runs Saturday & Sunday, September 28 – October 27.

13 nights at Jiminy Peak Mountain Resort
Experience the terror as you descend into the depths of Jiminy’s past as a haunted hold out. Ride through the darkness to the summit of Jiminy Peak where chaos lies in wait for you. Your haunt experience will last approximately 40 minutes… but will you? Friday and Saturday, September 27 – October 26 and October 30 & 31.

Pumpkin Fest at Whitney’s Farm & Market
U-pick pumpkins, haunted corn maze, hayrides, face painting, Uncle Pete’s Dairy Bar, petting zoo and more! Saturday & Sunday, 11Am – 5:30PM, September 21 – October 31.

Haunted Hancock
Join us at Hancock Shaker Village for an after-hours, spine-chilling evening of ghosts and mystery. Walk the dark paths of the village, hear true tales of ghostly sightings, and discover the Shakers’ role in the spiritualist movement. Tours are 90 minutes and include walking over uneven terrain and climbing several flights of stairs. Suitable for ages 12 and up. Thursdays in October.

The Incredible Naumkeag Pumpkin Show
In the spirit of the season, visit Naumkeag House & Gardens with our garden decorated with over 1,000 pumpkins and gourds, 400+ jack-o-lanterns, botanical arrangements, lights and more that will be guaranteed to surprise and delight visitors of any age. While this event will definitely inspire the spirit of Halloween, this is a non-scary event that is appropriate for all ages. Thursday – Sunday, October 3 – 27.

October 24
Luminaries: Exploring Stockbridge Cemetery
Join Norman Rockwell Museum educators Tom Daly and Mary Berle for a walking history tour of Stockbridge Cemetery. Find burial sites for Norman Rockwell, Elizabeth Freeman, the Sedgwicks and other notable town residents. Enjoy cider and donuts before the tour on the lawn adjacent the Old Town Hall. 5PM – 6PM

October 25
Pittsfield Halloween Parade
Ghosts and Goblins are everywhere at the Annual Halloween Parade, stepping off on Tyler Street at 7PM.

Naumkeag Haunted House
Prepare to be scared! A delightfully frightful experience that is not for the faint of heart! We’ve grown this event to become one of our areas best haunts and we continue the tradition this year with bigger scares and new surprises in the mansion and through the gardens. Recommended for ages 13 and up. Registration required. 6:30PM – 9PM.

October 26
The Best and the Wurst
Sample the best regional beers and hard ciders and enjoy live music on a late fall afternoon at Hancock Shaker Village. Additional food (old-world and Shaker-style) sausage, made with regionally sourced meats, and drinks will be available for purchase. 5PM – 7PM.

Flashlight Scavenger Hunt at Berkshire Museum
Lights out! Explore the Museum’s galleries with only a flashlight in this spooky, after-hours adventure. View the animals and visit the resident mummy, Pahat, all from a dark and shadowy perspective. Ages 5+.

Trick or Treat at Hancock Shaker Village
Trick-or-treat in costume as witches, ghosts, and goblins roam the Village. Learn how Shakers celebrated Halloween, get spooked with ghost stories and fortune-telling, bob for doughnuts, and hop on a “flying” Shaker broom. Meet Valerian the Garden Witch. Included with admission. 10AM – 3PM.

Spirited Train Ride
All aboard paranormal enthusiasts! Berkshire Scenic Railway’s Spirit Trains will be departing North Adams for a lantern-lit walk through Southview Cemetery with psychic medium Julie MacDonald. The 2-hour train ride leaves promptly at 5:30 pm from the platform near the Adams Visitor Center. Passengers are advised to dress weather appropriately; reservations required! 5:30PM – 7:30PM.

Saturday Night Fright – The Mount Ghost Tour
It starts with the sounds—creaking floors and slamming doors, fading footsteps down empty halls—a feeling of being watched, tingling taps on the shoulders, spectral shapes crouched in corners or gathered in front of fireplaces long gone cold. Tricks of the imagination in an old house once inhabited by a skilled writer of ghost stories … or something else? Take a ghost tour and decide for yourself. Not for children under 12. 5:45PM & 7PM.

Haunted Harry Potter Party at Blantyre
Join us for an all adult Halloween Party inspired by Harry Potter and the magical, mystical world or Hogwarts! Call to reserve. $125pp, 7:30PM – 11:30PM.

Naumkeag Haunted House
Prepare to be scared! A delightfully frightful experience that is not for the faint of heart! We’ve grown this event to become one of our areas best haunts and we continue the tradition this year with bigger scares and new surprises in the mansion and through the gardens. Recommended for ages 13 and up. Registration required. 6:30PM – 9PM.

October 27
Adams Children’s Halloween Parade
Children wearing Halloween costumes are invited to march from Adams Community Bank’s Center Street parking lot to the Adam’s Visitors Center, where cider donuts and drinks will be served and children will receive Halloween goodie bags. 3:45PM – 4:45PM

October 30
Spirited Tales: A Selection of Edith Wharton’s Ghost Stories
Celebrating Halloween with an evening of Edith Wharton’s spine-tingling ghost stories at The Mount! Professional actors will read a selection of Wharton’s gothic tales. Free for Members, $10 General. Spaces is limited; reserve online. 5PM.

October 31
Trick-or-Trivia! A Night of Spooky Halloween Fun
The evening will begin with a special performance by Miss Berkshire 2019 Jai Mason Miranda Moirai, who will lead us into Halloween Trivia. Grab your team and bring your thinking caps as you do not want to miss out on cash prizes, free classes at IS183, free VIP Tickets to the Only In My Dreams Events 2020 Dance party at the Colonial, and more! Wait the night is not over yet! Close the evening by participating in the costume contest for a chance to win even more goodies! 6PM.

10th Annual Sambaween
Join us at Spectrum Playhouse, Lee for the 10th Annual Sambaween featuring JBossa Triba and the Berkshire Bateria. $100 prize for Best Costume! Participate in the Thriller dance! Wine, Beer, and food available. Limited tickets available. 8:30PM.

The Nightmare Before Christmas
Halloween meets Christmas at the Mahaiwe Performing Arts Center in Henry Selick and Tim Burton’s stop-motion animated musical The Nightmare Before Christmas. Jack Skellington, the king of Halloween Town, happens upon a different world called Christmas Town and endeavors to celebrate the unfamiliar holiday. 7PM – 9PM.

Barrel Aged Halloween Party
There’s a few dark beers (not just stouts) that Bright Ideas Brewing has been holding onto for a bit, so why not tap them all on Halloween. Enjoy tunes by DJ Elixir and DJ iamsam from 7-10. Coolest costume gets a free tasting flight! 21+ event. 7PM – 11PM

Halloween Ghost Tour at The Mount
Take a special guided tour of the most haunted parts of the estate to find out who may still call The Mount home. $24 Adult; $20 Youth (12-18). 8PM & 10PM.

Naumkeag Trick or Treat
Fun, safe space for all-ages trick-or-treating along the Incredible Pumpkin Show route with special guests handing out candy. 5PM – 8PM.

Lenox Halloween Parade
The annual Lenox Community Center parade will begin at St. Ann’s Parish through town where goodies will be passed out at “trunk or treat.” Prizes will be awarded for the Most Creative, Scariest, and Kid’s Choice vehicles decoration. 5:30PM – 7PM.

Trick or Treat
Adams, 5:30PM – 7PM
Dalton, 5:30PM – 7PM
Florida, 6 PM – 8PM
Great Barrington, 5:30PM – 7:30PM
Lanesborough, 5PM – 7PM
Lee, At the Outlets from 5PM – 7PM
New Ashford, 5PM – 7PM
New Marlborough, 5PM – 7PM
North Adams, 5:30PM – 7PM
Pittsfield, 5:30PM – 7PM
Williamstown, 6PM – 7:30PM