Fall Events in the Berkshires

Ongoing

Make sure you stop in the gift shop for goodies!

Location: Berkshire Scenic Railway, Photo Credit: Laura Brennan

Berkshire Scenic Railway Fall Foliage Train Rides, North Adams

A 10-mile, hour-long round-trip experience between North Adams and Adams offering beautiful views of Mount Greylock and the surrounding Hoosac Mountain Range. The onboard narration is provided to offer educational, historical and cultural information.

Housatonic Heritage Walks

What better way to see the beautiful Berkshire foliage that up close and personal!

Haunted Hancock @ Hancock Shaker Village, Pittsfield

What happens in the Village after the last bell rings? Find out on this 90-minute after-hours tour. Your guide will lead you through the darkening Village where you will hear tales of ghostly sightings, learn about the Shakers’ role in the spiritualist movement, and perhaps catch a few spirit sightings of your own! The adventure concludes in the 1830 Brick Dwelling where hundreds of Shakers once made their home. Do any spirits remain? Fridays, October 6 – 27.

13 Nights at Jiminy, Hancock

Experience the terror as you descend into the depths of Jiminy’s past as a haunted holdout. This season tour the local prison of the Jericho Valley where you never know what will be lurking around the corner – you’ll pray for solitary…..and then ride through the darkness to the summit of Jiminy Peak where chaos lies in wait for you. Your haunt experience will last approx. 40 minutes but will you?

Friday Night Fright @ The Mount, Lenox

Creaking floors, slamming doors, and ghostly footsteps…The Mount’s haunted history includes it all! For over a century, The Mount has been home to writers, actors, wealthy families, hardworking servants, and teenage girls. Take a special guided tour of the most haunted parts of the estate to find out who may still call The Mount home. You never know who–or what–might happen to show up!

The Rocky Horror Show, Pittsfield
Let’s do the Time Warp again! Just in time for Halloween, this kitschy rock ‘n’ roll sci-fi musical is a live experience not to be missed! Audience participation is encouraged! Presented by the Pittsfield Town Players at Berkshire Community College Robert Boland Theatre. October 20 – 29.

Flashlight Scavenger Hunt at Berkshire Museum, Pittsfield
Come explore the Museum’s galleries with only a flashlight in a spooky, after-hours adventure. Saturdays, October 14 – 28, 6pm.

 

October 23

Ghosts & Legends Walking Tour, Pittsfield
Hosted by local folklorist and historian Joe Durwin, the 1 1/2-hour tour, recommended for ages 12 and up, explores some of the stranger-than-fiction history of downtown Pittsfield through the lens of its folklore, legends and mysteries. Tours take place after dark, so sturdy shoes and light-colored clothing are recommended. At The Common, First Street, 7 PM.

October 26

Luminaries: Exploring Stockbridge Cemetary, Stockbridge

Join Norman Rockwell Curator of Education Tom Daly for a walking history tour of Stockbridge Cemetery, which boasts the burial sites of such luminaries as Norman Rockwell, Elizabeth Freeman, the Sedgwick Family, and other notable town residents. A cider and donut reception will precede the tour on the lawn adjacent to the bell tower parking area at the Old Town Hall.

Ghosts & Legends Walking Tour, Pittsfield
Hosted by local folklorist and historian Joe Durwin, the 1 1/2-hour tour, recommended for ages 12 and up, explores some of the stranger-than-fiction history of downtown Pittsfield through the lens of its folklore, legends and mysteries. Tours take place after dark, so sturdy shoes and light-colored clothing are recommended. At The Common, First Street, 7 PM.

October 27

Halloween Party at Eastover Estate & Retreat, Lenox
Join us in the TALLY HO building at Eastover Estate and Retreat for a Halloween Party with DJ Dondada, DJ Le Grand and DJ Gusano Rojo. 18+ event, serving 21+. 8 PM; $15pp.

Halloween Parade & Pumpkin Walk-About, Stockbridge
Participants should meet at the corner of Main & Pine Street and march up Main Street to the Stockbridge Town Offices for cider & donuts. After the party, take a walk-about outside the Stockbridge Library and see lighted pumpkins carved by local businesses and area children. Spooky stories and more fun treat (or tricks??) will be offered inside. Rain cancels the parade. 6pm.

October 27 & 28

Haunted House at Naumkeag, Stockbridge
This Trustees property promises their haunted house will make you “run, scream and tremble with fright.” The ghost of the Choate’s gardener is back and he has set a harrowing course through the creaking Carriage House at Naumkeag. Scared? Bring your friends and your courage to join the fun.

October 28

Halloween at Hancock Shaker Village, Pittsfield
Come in costume for trick-or-treating throughout the Village. Visit the Brick Dwelling for ghost stories and fortune telling. Enjoy face painting & balloon art (fees apply), make-n-take slime, bobbing for doughnuts, and pumpkin decorating. Hear spooky stories in the barn. FREE to members/included in admission.

Pumpkin Carving Workshop, West Stockbridge
Join us at Turn Park for our last event of the season! Pumpkin Carving Workshop led by artist Dawn D’Aluisio and joined by other local artists.

Pumpkin Walk at Turn Park, West Stockbridge
Join us for our Pumpkin Walk to see the pumpkins carved earlier, during the Pumpkin Carving Workshop. Plan to enjoy a bonfire, hot cider, wine, food and music.

Trick or Treat in The Fields at Art Omi, Ghent NY
Join us at Omi at Fields Sculpture Park for a free afternoon of Halloween fun! We’ll provide art-making, hayrides, and a candy hunt amongst the sculptures. Come in your favorite costume, craft your own treat bag, and enjoy cider, popcorn and fresh apples in the park. 1 PM – 3 PM.

October 29

Halloween Séance Spirit Message Circle, Lenox
Berkshire Scenic Railway Museum presents Medium Julie MacDonald in a Séance designed specifically for communing more closely with Spirit. Enjoy a guided mediation followed by Spirit Communication.

Epic Halloween Party & Stained Glass Art Salon, Lenox
Join us at L’Atelier Berkshires for an Epic Halloween Party & Stained Glass Art Salon with Artist Talks by Debora Coombs and Iva Kailkow. Live Brazilian Jazz By Vita Kay and Horror’dourves and Spooky Cocktails by Amuse Catering. 5 PM – 8 PM.

Ghosts & Legends Walking Tour, Pittsfield
Hosted by local folklorist and historian Joe Durwin, the 1 1/2-hour tour, recommended for ages 12 and up, explores some of the stranger-than-fiction history of downtown Pittsfield through the lens of its folklore, legends and mysteries. Tours take place after dark, so sturdy shoes and light-colored clothing are recommended. At The Common, First Street, 7 PM.

October 31

Pittsfield Halloween Parade, Pittsfield
The Parade steps off at 7 PM on Tyler Street. A great event for the entire family!

Halloween Ghost Tour at The Mount, Lenox
Once again, The Mount presents a special tour on the spookiest night of the year!

Halloween Trick or Treat, Lee Premium Outlets, Lee
Lee Premium Outlets invites all area families to come dressed in their Halloween best for a festive (and free) evening of Trick-or-Treating at the center. Visit participating retailers for a treat bag and let the candy collecting fun begin! Whether you’re a ghost, goblin, princess or a witch… Lee Premium Outlets hopes to see you for some tricks and treats! 5 PM – 7 PM.