Your Three-Day Fall Getaway to the Berkshires

The Berkshires is at its most vibrant and enchanting in autumn. Crisp mornings, fiery foliage, and cozy small-town charm set the scene for an unforgettable escape. Rolling hills burst into a kaleidoscope of color painted across the mountains, orchards brim with ripe apples and pumpkins, and every bend in the road offers an Instagram-worthy photo op.

Fall here is about slowing down; sipping warm cider or mulled wine, strolling through cozy downtowns, and savoring farm-to-table flavors alongside the beauty of the foliage. This three-day itinerary takes you across the Berkshires, giving you a perfect taste of all the region has to offer.

Mount Greylock. Photo courtesy of Nick Mantello.

Day One

Base yourself in the northern hills with a stay at the Blue Vista Motor Lodge or the centrally located Hotel Downstreet in North Adams. 

Begin your morning in Williamstown with a hearty breakfast at The Spring Street Market & Cafe, followed by a leisurely stroll down Spring Street. Pop into Tea & Boba Lounge for a cozy drink before heading to The Clark Art Institute, where world-class art collections blend seamlessly with walking trails drenched in fiery foliage. Don’t miss the chance to sit along the reflecting pool while admiring the colorful foliage surrounding.

Afterward, make your way to MASS MoCA in North Adams. Its sprawling industrial galleries are a feast for the imagination, and the converted mill buildings themselves glow against the backdrop of fall colors. Refuel at the inventive Casita for lunch or stop into Bright Ideas Brewing for the craft beer and atmosphere. Next, make your way up Mount Greylock before the roads close at the end of October. The summit, framed by the Veterans War Memorial Tower, offers panoramic views stretching across multiple states—arguably the crown jewel of fall in the Berkshires. If you want a bit of history with your foliage views, consider hopping on the Hoosac Valley Train Rides in Adams where you will ride the 1950s classic speedliner through the local vistas. 

After coming down the mountain, cap off the day with some shopping at Lanesborough Local Country Store. You’ll find homemade treasures, fun blast from the past items, and even a dessert (and ice cream scoop – or two)! Or if you’re looking for a more immersive experience, check out Ioka Valley Farm. Pick your own pumpkins, grab some of their fresh pure maple syrup, wander through the mini corn maze, and visit the farm animals! In the evening, enjoy dinner at Common Table, where the menu celebrates local flavors and fresh ingredients. Sit outside near the firepits with a cocktail or warm beverage for a beautiful fall view. 

Whitney’s Farm Market. Photo by Great Sky Media.

Day Two

The next day, make your way to the central county. Swing by Whitney’s Farm Market for cider doughnuts, pumpkins, and autumn treats. In the heart of the county, check into Hotel on North in Pittsfield for a stylish boutique stay, Vacation Village for luxury condominium style units, or opt for the romantic Seven Hills Inn in Lenox.

Start your day with a classic breakfast at Otto’s Kitchen and Comfort, beloved for its comfort food. Then step back in time at Hancock Shaker Village, where 19th-century barns and gardens sit framed by blazing maple trees. Consider stopping by Balderdash Cellars just down the road for a wine tasting and gaze over the foliage covered water! 

No fall trip is complete without apple-picking! Pick your own at Bartlett’s Orchard or include a cider tasting at Hilltop Orchards & Furnace Brook Winery, then browse treasures at Susan Silver Antiques. Make your way back to Pittsfield for dinner at Mazzeo’s or Proprietor’s Lodge. Don’t forget to treat yourself to indulgent sweets at Chocolate Springs Cafe along the way! 

Stroll through downtown shops like Bottomless Bricks, or catch a show at Barrington Stage Company. Before turning in, grab a local brew at Hot Plate Brewing and enjoy some local entertainment. 

Catamount Mountain Resort

Day Three

Anchor your final day in the south county, choosing between the storied Red Lion Inn in Stockbridge, Little Lion in Great Barrington, or the chic Black Swan Inn in Lee.

Fuel up with fresh-baked goods from Berkshire Mountain Bakery in Housatonic and grab lunch at Pleasant and Main before exploring two of the region’s most impressive culturals: the Norman Rockwell Museum and Naumkeag. Naumkeag’s Incredible Pumpkin Show is a not-to-be-missed fall staple in the Berkshires! 

Then, take a scenic drive down Route 7 through Sheffield and Egremont, stopping at Hoffman Pottery for local crafts or Berkshire Mountain Distillers for a tasting. Want to explore some fall adventure? Glide above the treetops on the Catamount Catamonster! 

Cap the afternoon with a sweet treat from High Lawn Farm or Robin’s Candy Shop! Don’t forget to stop by Guido’s Fresh Marketplace for some fresh travel snacks. While in Great Barrington, be sure to visit the newly unveiled W.E.B. Du Bois sculpture and learn more about Great Barrington’s most famous native son. As the sun sets, dine lakeside at Mint Indian, the charming historic Old Inn on the Green, or enjoy the warm mountain-lodge atmosphere at Dream Away Lodge. 

In the morning before hitting the road, end your time in the Berkshires on a sweet note with a custom creation from Shire Donuts.

A Cozy Send Off

The Berkshires shine in every season, but autumn holds a special magic. October is peak foliage time and November offers quiet trails and cozy inn stays before winter sets in. This weekend itinerary offers a taste of the region’s richness, but the real joy of the Berkshires in fall is slowing down—crunching leaves underfoot, sipping cider, and letting the colors of the hills take your breath away. Wherever you stay, whatever you eat, and however you spend your time, the Berkshires in fall will leave you enchanted and likely planning your next visit before you’ve even left. To truly “see it all” we recommend you extend your visit or come back again! Visit in every season to see the true magic we host #intheberkshires. 

Before your visit, be sure to check out our local event calendars for seasonal festivals, coupons and discounts, and events, which vary year to year. You won’t want to miss it! Looking for more ways to enjoy the vibrant foliage? These routes offer scenic views—plus great places to eat, stay, and explore!

For even more inspiration, itineraries, and not to miss spots, visit Berkshires.org and request your free copy of The Official Guide to the Berkshires, the ultimate resource for anyone planning a trip to the region, year-round.

Find more of what’s happening in the Berkshires this fall here.

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