Experience the magic of autumn in the Berkshires with our ultimate Fall Travel Guide. Known for its rolling mountains and brilliant foliage, the Berkshires is one of New England’s most iconic destinations for a seasonal getaway. This guide highlights the best things to do, see, and taste during fall—from world-class art museums like MASS MoCA and the Norman Rockwell Museum to charming cafés, award-winning restaurants, and cozy farm-to-table dining. Outdoor lovers will find endless hiking trails with sweeping views, from Monument Mountain to Mount Greylock, while foodies can sip and savor at local wineries, breweries, cideries, and distilleries. Whether you’re planning a weekend escape or a longer road trip, our Berkshires guide covers top attractions, scenic drives, cultural experiences, and hidden gems that make autumn here unforgettable. Discover where to eat, drink, hike, and explore, and start planning your perfect Berkshires fall getaway today.
Historic
Sign up to see location
Edith Wharton’s historic Gilded Age estate
Restaurant
Sign up to see location
All-day breakfast & brunch classics
Bar
Sign up to see location
Cocktail bar & restaurant
Restaurant
Sign up to see location
The Club Room is our signature dining space
Culture
Sign up to see location
Renowned summer theater performances
Museum
Sign up to see location
Art, history, and science exhibits
Museum
Sign up to see location
Outdoor sculpture park with views
Sightseeing
Sign up to see location
Charming art gallery in Massachusetts
Sightseeing
Sign up to see location
Art hub in Pittsfield
Museum
Sign up to see location
Artists' retreat and studio
Museum
Sign up to see location
Art museum with diverse exhibitions
Museum
Sign up to see location
Norman Rockwell art museum
Museum
Get access to see location
Art and nature in harmony
Museum
Get access to see location
Contemporary art museum in Massachusetts
Café
Get access to see location
Charming local coffee shop
Café
Get access to see location
Charming dessert spot in Massachusetts
Café
Get access to see location
Cozy creperie with delicious options
Café
Get access to see location
Cozy cafe with delicious food
Café
Get access to see location
Cozy coffee roastery and cafe
Café
Get access to see location
Charming Lenox bakery with pastries
Café
Get access to see location
Charming bakery with delightful pastries
Café
Get access to see location
Charming getaway in Massachusetts
Restaurant
Get access to see location
Cozy eatery with delicious comfort food
Restaurant
Get access to see location
Casual fry restaurant in Massachusetts