There is nothing quite like autumn in Berkshire County. The vivid display of foliage sweeping across the hills, and that cozy, distinct turn in the season attract plenty of visitors–but if you’re making your move to our area full-time, we have all the tips on how the locals make the best of it.
As area experts who make it our business to know what towns and amenities will make your next chapter a success, we’ve rounded up nine of our favorite fall activities across the region.
1. Stroll around a Fall Festival
Fall in the Berkshires kicks off with some of our favorite annual traditions. Whether the focus is live music or local foods, some of our favorites include:
FreshGrass at MASS MoCA: a roots music festival that comes to North Adams every September. You’re likely to see some familiar names as well as new favorites!
Harvest Festival at Berkshire Botanical Garden: An annual festival in Stockbridge that’s perfect for the whole family. Enjoy a vendor market, a community scarecrow design competition, square dancing and more!
The Apple Squeeze in Lenox: Downtown Lenox comes alive at the end of every September with local bites, craft beer, live music, beautiful trinkets and plenty of activities for the kids.
2. . Visit a local farmstand, orchard, or tasting room
Make the most of the gorgeous fall weather while it lasts! Gather up family and friends to stock up on fresh cider, local produce, and seasonal treats.
Pick apples and enjoy pristine views at Bartlett’s Apple Orchard in Richmond.
Pick your favorite pumpkin and explore seasonal displays at Whitney’s Farm Market in Cheshire.
Stop into the cidery at Hilltop Orchards and weigh in on the great debate of “who has the best cider donuts?”
Sit in one of the iconic red adirondack chairs of Balderdash Cellars in Richmond for a crisp glass of wine with stunning lakeside scenery.
Swing by Highlawn Farm in Lee for fresh dairy, ice cream, and iconic rural landscapes.
3. See the glow of the Naumkeag Pumpkin Show
For a truly magical evening, head to Stockbridge for the annual Incredible Naumkeag Pumpkin Show. The historic estate’s famous gardens come alive at night with thousands of intricately carved, glowing jack-o'-lanterns and fall light displays. It is a hit for all ages—just be sure to reserve your tickets early!
4. Visit the Ghosts at Ventfort Hall
If you like a little ghost-story history with your fall aesthetic, visit Ventfort Hall Mansion and Gilded Age Museum in Lenox. Known for its stunning architecture and documented ghost sightings, the mansion hosts special spooky tours, Victorian tea sessions, their new fundraising gala the “Masquerade Macabre” and paranormal investigations throughout the autumn season.
5. Take in the Foliage by Foot, Car, Trail, or Train
Whether you prefer a high-elevation hike or a leisurely drive, there are endless ways to surround yourself with peak fall color:
Drive to the summit of Mount Greylock for panoramic, multi-state foliage views.
Hike up Monument Mountain for sweeping vistas over the Housatonic River Valley.
Take a relaxed bike ride or walk along the paved Ashuwillticook Rail Trail.
Book a scenic train excursion with the Berkshire Scenic Railway for a nostalgic look at the changing landscape
6. Join a cozy social group
As the evenings get cooler, warm up inside and connect with neighbors at local community hangouts:
Gather your friends and show off your knowledge on Tuesdays for Hot Plate’s ongoing Taproom Trivia series in Pittsfield.
The Clark Collage Club meets on the third Wednesday of the cooler months in Williamstown’s renowned fine arts museum.
The Ramsdell Knitting Group in Great Barrington welcomes teens and adults of all skill levels to come craft.
7. Forget Summer Stock: See a staged show this autumn
Our local theatres are famous for their summer programming, but many continue to offer amazing shows during the fall as well:
The Mahaiwe Theatre continues to offer jazz, opera, contemporary and everything in between–along with more intimate shows like comedy nights in their Indigo Room.
Interested in seeing some young, local talent? Shakespeare and Company hosts students from 10 local high schools at the Tina Packer Playhouse in Lenox to showcase the Bard’s plays. Shake & Co also switched gears to stage works inspired by Jane Austen each year as the weather cools.
Berkshire Theatre Group continues to show new plays, tribute shows,children’s programming, and more throughout the year.
8. Catch a Classic Halloween Movie at an Independent Theater
We advise you to skip watching all your Halloween classics on Netflix–instead, enjoy a nostalgic movie night at one of our beloved local independent theaters:
Images Cinema: on the north side of the county, enjoy curated series like “Nightmare on Spring Street” and “Monster Movie Matinee.” From black-and-white science fiction movies, to new works by directors under age 30, every age is bound to find something to be excited about at Images. Outside of seasonal “spooky” offerings, you’ll also find film series dedicated to other perspectives, from the Indigenous Peoples Film Festival to collaborations with different departments at Williams College.
The Triplex Cinema: On the south side of the Berkshires, the Triplex also holds the live-scored silent horror films you’re craving to see this season. The “Triplex of Terror” series unites with the Great Barrington Public Libraries to offer locals a true page-to-screen experience, with classics like “The Shining” and “Rosemary’s Baby” taking center stage.
9. Lace Up for a Fall Race (or Cheer from the Sidelines!)
Fall is peak racing season in the Berkshires. Whether you are competing or spectating, the energy is infectious at iconic events like:
Harvest Run at Berkshire Community College: takes place every September with a 5K trail run, and 1-mile “fun run” for kids.
Josh Billings Runaground Triathlon: A beloved bike-canoe/paddleboard-run triathlon, featuring a lap around the Stockbridge Bowl and finish-line party on the grounds of Tanglewood.
Soldier On Veterans Day 5K: A road race that welcomes runners and walkers in Dalton to support Soldier On.
If you're seeking a Berkshire County home to call your own, don't hesitate to get in touch. Our agents would love to guide you into a lifestyle that suits you in every season!
