1Berkshire Shares 20 Ways to Enjoy Fall Foliage and Seasonal Experiences in the Berkshires

From Mount Greylock and Bash Bish Falls to apple orchards, and small-town exploring, the Berkshires enters one of its most colorful seasons

NEW YORK, NY, UNITED STATES, October 2, 2026 /EINPresswire.com/ -- Fall does not arrive in the Berkshires all at once. The transformation begins gradually. September mornings become cooler, the first leaves brighten along mountain roads, apples ripen in local orchards, and restaurant menus make room for the flavors of the harvest. Then the green landscape increasingly gives way to the reds, oranges and golds that have made the Berkshires one of New England’s best-known autumn destinations.

Because the region encompasses 32 communities, river valleys and the highest elevation in Massachusetts, there is no single weekend that defines fall in the Berkshires. Color typically begins emerging at higher elevations and in the northern Berkshires before moving south, creating opportunities to experience the season well into October.

From classic foliage destinations to some less expected stops, 1Berkshire has identified 20 ways to experience fall across the region:

1. See Massachusetts from the top of Mount Greylock. At 3,491 feet, Mount Greylock is the highest point in Massachusetts. The seasonal road through Mount Greylock State Reservation winds toward the summit, where the Veterans War Memorial Tower overlooks the surrounding mountains and valleys. Miles of trails offer another route to experiencing the mountain and its autumn scenery.

2. Explore the Ashuwillticook Rail Trail. The 12-mile paved trail through Cheshire and alongside Cheshire Reservoir provides cyclists and walkers with views of mountains, forests, water and wildlife. Its relatively accessible terrain also makes it an option for families seeking an outdoor foliage experience without a strenuous mountain hike.

3. Go apple picking. Apples are as much a part of a Berkshire autumn as changing leaves. Bartlett’s Orchard and Hilltop Orchards & Furnace Brook Winery are among the region’s destinations for pick-your-own apples, cider and seasonal treats. September can be an especially active time in the orchards, even before foliage reaches its peak.

4. Experience Bash Bish Falls. A short hike through dense hardwood forests leads to Massachusetts's tallest single-drop waterfall. Cascading nearly 80 feet into a dramatic emerald pool between soaring rock faces, Bash Bish Falls offers a striking focal point framed by vivid autumn color. Straddling the border of New York and Massachusetts in the southern Berkshires, the park's scenic trails provide multiple vantage points for admiring both the falls and the surrounding mountain views.

5. Get spooky at The Mount. The Lenox estate of author Edith Wharton comes alive with seasonal atmosphere each autumn. Visitors can take guided Ghost Tours after dark to explore the historic home and grounds while hearing eerie tales of strange occurrences and paranormal encounters. Surrounded by formal gardens and woodlands bathed in fall foliage, The Mount combines New England literary history with a touch of supernatural intrigue during the Halloween season.

6. Join the Adams Ramble. Adams Ramble Weekend combines outdoor recreation with a community celebration beneath Mount Greylock. RambleFest on October 11th features music, local food and craft beverages, followed on October 12th by the traditional hike toward the summit of Mount Greylock. The weekend also provides opportunities for hiking, cycling and exploring Adams during foliage season.

7. Celebrate the harvest at Berkshire Botanical Garden. The Berkshire Botanical Garden Harvest Festival transforms the garden’s 24 acres into an autumn celebration of community, agriculture and the natural world. Activities traditionally include hayrides, a hay maze, pony rides, face painting, live music, food, shopping and family programming.

8. Step into history at Hancock Shaker Village. Historic buildings, fields and gardens make Hancock Shaker Village particularly suited to a New England autumn. In addition to exploring Shaker history and daily life, fall visitors can encounter seasonal programming at the Pumpkin Extravaganza on October 17th.

9. Spend an autumn evening at Naumkeag. The historic Stockbridge property is known for its distinctive gardens and landscape, which take on a different character as the season changes. The annual Incredible Pumpkin Show adds another layer of fall color, while nearby Stockbridge provides restaurants, shops and opportunities for a village stroll.

10. See the northern Berkshires by train. Hoosac Valley Train Rides, operated by the Berkshire Scenic Railway Museum in Adams, provide a slower way to see the landscape. Seasonal excursions allow passengers to experience the northern Berkshires and its changing foliage from the rails.

11. View foliage from the water. Berkshire fall color can also be experienced by kayak or canoe. Stockbridge Bowl, Laurel Lake, Onota Lake, Pontoosuc Lake, Richmond Pond, Goose Pond and Lake Buel are among the waterways offering a different perspective on the autumn landscape. BerkshiresOutside.org provides additional information on outdoor recreation throughout the region.

12. Add some altitude and adrenaline. Jiminy Peak Mountain Resort, Catamount Mountain Resort, Berkshire East Mountain Resort and Bousquet Mountain offer alternatives to traditional hiking. Depending on seasonal schedules and conditions, activities can include scenic rides, ziplining and aerial adventures that provide elevated views across the landscape.

13. Discover Natural Bridge State Park. North Adams is home to one of the region’s more unusual geological landscapes. Natural Bridge State Park contains a natural marble bridge and the remains of an abandoned marble quarry, creating a setting markedly different from the traditional mountain vistas associated with Berkshire foliage.

14. Pick the perfect pumpkin. Stroll through local pumpkin patches to find the perfect gourd for your fall carving adventures. Whitney’s Farm Market Features Pumpkin Fest every weekend through October, with rows of pumpkins to explore, corn mazes, and plenty of seasonal fun along the way. Or, stop by Ioka Valley Farm for pumpkin slingshot fun, fresh maple syrup tastings, and seasonal treats. A pumpkin-picking outing is the quintessential Berkshires fall experience, so don’t forget to snap a few photos while you’re there!

15. Find a quieter fall landscape at Notchview. Notchview in Windsor offers miles of trails through woodland and open landscapes. The property provides a quieter alternative for experiencing changing leaves away from some of the region’s better-known foliage destinations.

16. Taste the season. Autumn also changes what appears on Berkshire tables, with apples, squash, mushrooms, root vegetables, maple and cider among the ingredients associated with the season. Dining choices stretch across the county, including Casita, The Barn Kitchen and Bar and Freight Yard Pub in the northern Berkshires; Otto’s Kitchen & Comfort and Mazzeo’s in Pittsfield; and Mint Indian, Old Inn on the Green and Dream Away Lodge farther south. Guido’s Fresh Marketplace and the Berkshire Food Co-op offer picnic provisions and locally produced foods, while Hilltop Orchards and Bartlett’s are among the stops associated with another fall staple: cider donuts.

17. Make the view part of an overnight stay. Lodging across the Berkshires places visitors within the autumn landscape. Northern and central Berkshire options include The Porches Inn at MASS MoCA, Blue Vista Motor Lodge, Hotel Downstreet, Hotel on North and The Guest House at Field Farm. Farther south are The Inn at Stockbridge, The Red Lion Inn and Little Lion, while area campgrounds provide another way to spend a night surrounded by foliage.

18. Explore a Berkshire downtown without an itinerary. Williamstown, North Adams, Lenox, Stockbridge, Adams, Lee, Great Barrington, Sheffield and West Stockbridge each offer different combinations of shops, bookstores, galleries, cafes, restaurants, architecture and local history. Leaving time simply to walk a downtown or village center can provide a different perspective on the region beyond its major attractions.

19. Take the long way along the Mohawk Trail. Route 2 and the historic Mohawk Trail wind through the mountains between North Adams and Williamstown. The Hairpin Turn offers one of the region’s recognizable vistas over the Hoosac Valley, but the broader appeal is the journey itself, with changing landscapes and opportunities to stop along the route.

20. Leave room for the unexpected. A Berkshire fall itinerary does not necessarily have to account for every hour. Farm stands, unexpected overlooks, trails, galleries and small-town discoveries are often found between planned destinations. The region’s network of country roads and communities leaves room for exploration beyond a predetermined schedule.

About The Berkshires:
Less than three hours from New York City and Boston, the Berkshires offer culture and adventure year-round. The surrounding mountains provide plenty of opportunity for outdoor excursions in all seasons while world class culture and entertainment, along with a deeply rooted food culture and an array of lodging options amidst picturesque towns, set this region apart. The Berkshires is a picturesque rural destination with a cultural scene to rival far larger urban dwellings. For more info visit berkshires.org.

About 1Berkshire:
1Berkshire is a county-wide marketing and economic development organization that works to simultaneously preserve, position, and promote Berkshire County’s profound sense of place. Its mission is to advance Berkshire County’s economy by advocating for the business community and attracting visitors. Powered by membership, 1Berkshire provides programs that connect businesses with resources and potential customers, as well as develop future leaders and support entrepreneurs. For more information, visit 1Berkshire.com

For more information about 1Berkshire (the regional tourism and economic development organization) visit www.1berkshire.com

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Norah Lawlor
Lawlor Media Group, Inc.
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