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.

September 23

Indonesian Country Fair at Turn Park, West Stockbridge

Turn Park will be transformed into an Indonesian archipelago highlighting its six main islands – Java, Sumatra, Kalimantan, Sulawesi, Bali and Papua. Upon arrival, travelers will be handed a “Passport” with six empty circles. During their visit, “tourists” can “island hop” to collect six stamps from the six costumed tour guides while enjoying the wealth of Indonesia. There will be food, dance, music, arts & crafts, as well as young Indonesian artists.

Fall Foliage Children’s Races and Family Fair, North Adams
A foot race and family fair. This event is open to all ages, with categories for various age groups, and awards for group winners. The fair includes obstacle courses, games, give-a-ways, entertainment, and food. Children’s Fair booths are hosted by local community organizations. 9 AM – 12 PM.

September 23 & 24

Head to the Hancock Shaker Village Country Fair this year!

Location: Hancock Shaker Village, Photo Credit: Quinn Gladu

Country Fair at Hancock Shaker Village, Pittsfield

Celebrate the bounty of the harvest on the spectacular grounds of Hancock Shaker Village, with a food truck rodeo including Big Elm Brewing and Balderdash Cellars, a farmer’s market and the best local and regional crafts — all for sale! Listen to live music, watch agricultural demonstrations, and even jump in a pile of hay! Just what a fall festival should be.

Lenox Apple Squeeze, Lenox

Join local shops, restaurants, artisans, musicians, farm stands, & performers as Lenox celebrates the apple harvest with a fun & engaging free street festival for all ages.

September 24

Chili & Chowder Festival, Pittsfield

Bring friends and family and join in the fun! Food, beer & wine, music, children’s activities, raffles, lawn games and more.

September 28

Downtown Bike Around – Light Up your Bike Fall Foliage Bike Parade & Rodeo, North Adams
Join the Downtown Bike Around when we hope to gather 100 cyclists for our bike parade! Meet at the lot at 5pm for a bike safety course and bike decorating! Gather at 5pm at St. Anthony’s Parking Lot. Ride begins at 6:30 PM.

September 29

Annual Fall Foliage Children’s Parade, North Adams
Children from throughout the Northern Berkshire’s are encouraged to make costumes and enter the parade. This year’s theme is “Magic in the Berkshires”. Participants must arrive at the corner of Main and Eagle streets at 5 Pm with the parade stepping off at 5:30 PM.

October 1

Fall Foliage Parade, North Adams

Join us for this memorable fall event in the Berkshires. The North Adams Fall Foliage Parade is in its 62nd year and this year the theme is Magic in the Berkshires! Steps off at 1 PM on Curran Memorial Highway and runs down Main Street and ends on Ashland Street.

October 7 & 8

Harvest Festival at Berkshire Botanical Garden, Stockbridge

October 8

Ramblefest 2017, Adams
Jam with License to Groove and enjoy local favorite food vendors BIGG Daddy’s, Desperado’s,Cliff’s Smokin’ Backyard Barbeque & Catering, Adams Lions Club. Bright Ideas Brewing and Wandering Star Craft Brewery will be quenching our craft brew thirst! Unique artisans and crafters, outdoor recreational interests and fun fall activities for kids!

October 9

50th Annual Greylock Ramble, Adams
Each Columbus Day for the past 50 years, thousands of people have made the hike to the highest spot in Massachusetts. Free shuttles take hikers from downtown Adams to and from the base of the Cheshire Harbor Trail. Use of the shuttle is strongly recommended, as parking near the trail is very limited. There are refreshments and souvenirs available for purchase at the top, but the hike itself and the spectacular views are free!

Live music, crafts, food, haunted house and more!

October 13 & 14

Purgatory Road Holidaze, Dalton

Dare to enter our Haunted Corn Maze? Your holiday favorites will be waiting for you! 7 PM-10 PM.

Naumkeag Pumpkin Trail, Stockbridge
Along the pumpkin-lit garden trail you will meet nocturnal woodland creatures from our local forests who will emerge to share their stories. Learn fun facts about some of your favorite critters. This is a non-scary event for all ages! Costumes welcome. This event is rain or shine and flashlights are encouraged and all children get in free.

October 14

Spirited Fall Foliage Berkshire Scenic Railway Train Ride, North Adams
Enjoy traveling on the area’s favorite scenic train ride with Medium Julie MacDonald and tour Southview Cemetery, receive tutoring on tuning in to the energies in this beautiful Victorian style burial ground and receive information and messages from the spirit world. 5:30 PM.

October 20

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 20 & 21

Purgatory Road Holidaze, Dalton

Dare to enter our Haunted Corn Maze? Your holiday favorites will be waiting for you! 7 PM-10 PM.

October 21

Spirited Fall Foliage Berkshire Scenic Railway Train Ride, North Adams
Enjoy traveling on the area’s favorite scenic train ride with Medium Julie MacDonald and tour Southview Cemetery, receive tutoring on tuning in to the energies in this beautiful Victorian style burial ground and receive information and messages from the spirit world. 5:30 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.

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.

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!