EXPLORE THE BERKSHIRES
Get out there.
Then come back to ButtonBall.
A mountain morning. A museum afternoon. A bookstore you disappear into for an hour. From South Egremont, the southern Berkshires and neighboring Connecticut and New York offer plenty of ways to fill a day. Leave a little room for dinner, live music, and a very comfortable bed back at ButtonBall.
Farm stops and cider detours
Some outings come with a souvenir. These tend to come with cheese, apples, or a bag of cider doughnuts that mysteriously empties on the way home.
High Lawn Farm
Lee, MA · Farm visit and creamery
Meet the Jersey cows, visit the calf nursery when open, and stop at the Farmstead Creamery for ice cream, cheese, and local goods. Check barn access before a visit focused on the animals.
Hilltop Orchards
Richmond, MA · Cidery and orchard
Cider and wine tastings, orchard walks, and cider doughnuts make a convincing afternoon plan. Apple picking follows the harvest season; ask about cidery tours and production access rather than assuming pressing is happening when you arrive.
Bartlett’s Orchard
Richmond, MA · Farm market and seasonal picking
A stop for apples, cider, doughnuts, and baked goods. Check the orchard’s latest harvest and picking updates before making apple picking the main event.
Fresh air looks good on you
Monument Mountain
Great Barrington, MA
Earn your view with a hike above the Housatonic Valley. Choose a route that suits your group and check the official trail map and conditions.
Bash Bish Falls State Park
Mount Washington, MA
Make time for a waterfall outing near the Massachusetts–New York border. Check the state park’s current access, parking, and trail guidance before setting out.
Shops worth getting sidetracked in
Ward’s Nursery and Garden Center
Great Barrington, MA
For gardeners, houseplant collectors, and anyone who believes there is room for just one more pot. Browse plants, garden supplies, gifts, and seasonal displays.
Lakeville Books and Stationery
Great Barrington, MA
Pick up your next fireside read at the Great Barrington shop. A good book is an entirely respectable reason to spend the rest of the afternoon back at the Inn.
Oblong Books
Millerton, NY
Cross into New York for a bookshop browse and a wander around Millerton. Leave enough space in your bag for the book you came for and the others you didn’t.
Art with an afternoon attached
Norman Rockwell Museum
Stockbridge, MA
Explore Norman Rockwell’s work and the wider world of American illustration. Pair your museum visit with time in Stockbridge before returning to the Inn.
Worth making a day of it
MASS MoCA
North Adams, MA · Farther afield
Go north for contemporary art on a former factory campus. Give yourself time to explore, and check admission details and any installations that require advance reservations.
Make a weekend of a performance
The Mahaiwe Performing Arts Center
Great Barrington, MA
Build an evening around a concert, comedy show, dance performance, or screening at this historic downtown theater. Check the calendar and book your seats.
Tanglewood
Lenox, MA · Summer concerts
A Berkshire summer deserves a little music under the sky. Explore the Boston Symphony Orchestra’s summer home and choose a performance that fits your stay.
Music Mountain
Falls Village, CT · Summer festival
Chamber music and jazz make a fine reason to head into the Connecticut hills. Check each concert listing for its date and venue, especially outside the summer festival.
A little horsepower
Lime Rock Park
Lakeville, CT · Scheduled events and programs
Racing, car shows, and driving programs in a countryside setting. Choose an event from the calendar; track access and driving experiences depend on the scheduled program.
Ski all day. ButtonBall all night.
Catamount Mountain Resort
South Egremont, MA / Hillsdale, NY · Seasonal adventures
Ski or snowboard in winter; check the seasonal calendar for aerial adventure and ziplining when the snow is gone. One mountain, several good reasons to get outside.
Ski Butternut
Great Barrington, MA · Winter
Build a winter getaway around a day on the slopes. Check lift tickets, lessons, rentals, and current conditions before heading out.
Bousquet Mountain
Pittsfield, MA · Winter
Another Berkshire option for skiing and snowboarding, with lessons and night skiing on scheduled dates. Check the mountain’s current operating calendar.
For people who brake for gardens
Naumkeag
Stockbridge, MA · Seasonal admission and special events
A historic estate with distinctive gardens and Berkshire views. Plan around the current garden season or a ticketed seasonal event, and reserve ahead when required.
Trade Secrets
Annual garden tours, rare plants, and garden antiques
Rare plants, garden antiques, and enough inspiration to reconsider your entire backyard. The organizer has announced May 15–16, 2027; follow its website for that year’s venues, garden tours, tickets, and sale details.
Three ways to spend a ButtonBall day
Country wandering
Visit High Lawn Farm, then make a Richmond orchard stop. Check visitor and tasting hours before heading out.
Art and browsing
Start at the Norman Rockwell Museum, wander Stockbridge, and browse the shops in Great Barrington.
Snow day
Choose Catamount, Butternut, or Bousquet, then return for dinner and a Barn show when the calendar lines up.
The best part is coming back
Dinner at the Inn. A drink and a show at the Barn. A room close enough that the journey home is the easy part. Make ButtonBall your base, then see where the day takes you.
Explore the Restaurant · See What’s On at the Barn · Book Your Stay
Hours, tickets, visitor access, and seasonal activities can change. Follow each destination’s official link for current details.
Have something we should know about?
We’re always on the hunt for fun things to do in the Berkshires. If you’d like to be considered for inclusion, send a short description, your website link, and a high-resolution photo you have permission to share to info@buttonball.com.