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 11
Spirits in The Corn Maze
Whitney’s Farm Market & Garden Center presents Spirits in The Corn Maze featuring local beer, wine and spirits tasting in the Haunted Corn Maze. 6PM – 8PM

October 11 & 12
Naumkeag Pumpkin Trail
Follow the Naumkeag Pumpkin Trail for a magical treat. Along the pumpkin-lit garden trail you will meet nocturnal woodland creatures from our local forests will emerge to share their stories. Learn fun facts about some of your favorite local critters. This is a non-scary event for all ages! Costumes welcome. Flashlights are encouraged. The trail is not stroller friendly and does have uneven footing. Children free. Register today as this event fills up quickly. 5:30PM – 8PM

Purgatory Road Ouija!
Let the Ouija Board draw you in for the final time! Walk your way through a 2-acre haunted corn maze. Children 12+.

October 12
Annual Pub Crawl
This year marks the 10th year of our Zombie Pub Crawl! Hundreds of Zombies will fill the streets and pubs of Downtown Pittsfield. They may be looking for BRAINS so BEWARE! Creative costumes are encouraged and rewarded. 21+ event.

Kid’s Fall Fest!
Join us at the Lee Farmers’ Market for pumpkin painting, games, scarecrow contest, face painting, popcorn, bake sale, and music! Food available for purchase. 10AM – 12PM.

Fall Festival at Jiminy Peak Mountain Resort
Join us for our annual Fall Festival celebration featuring sales on snow sports equipment and apparel, a craft fair, scenic chairlift rides and fun at Mountain Adventure! 9AM – 5PM.

October 12 & 13
Berkshire Botanical Garden Harvest Festival
Children’s activities, pony and hayrides, games, live entertainment, over 100 regional artisan vendors, a farm market, tag and plant sales, and education offerings! 10AM – 5PM

October 13 & 14
RambleFest & Greylock Ramble
Party on Sunday! Held outdoors at the Adams Visitors Center at 3 Hoosac Street, admission is free to a festival full of music, food and fun in celebration of autumn in the Berkshires. 12PM – 4PM. Hike on Monday! The Annual Greylock Ramble is the ultimate way to experience autumn in the Berkshires. Free shuttles take hikers from downtown Adams to and from the base of the Cheshire Harbor Trail from 8 am to 4 pm. Using the shuttle is strongly recommended, as parking near the trailhead is very limited.

October 19
15th Annual Pittsfield City Jazz Festival
Presenting Jazz vocalists Sephanie Nakasian & Veronica Swift, Cuban pianist and Jazz visionary Dayramir Gonzalez and more!

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.

October 20
Children’s Pumpkin Painting Workshop
Join us as at Ventfort Hall in Lenox as we prepare for Halloween by painting pumpkins here at the mansion. While pumpkins dry, there will be opportunities to have some spooky snacks and craft other autumnal decorations. 12PM – 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.

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.

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 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.

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.