Things To Do
Balderdash Cellars
Enjoy a glass of wine or beer on an adirondack chair overlooking Richmond Pond. While you're in the neighborhood, grab apple cider donuts from Bartlett's Orchard.
Lenox
A cute downtown that's great for walking around the shops and grabbing coffee or lunch. Our favorite restaurants in Lenox are Haven, Alta or Boema. Heritage House is great for pub food and a beer. MacKimmie Co or Design Menagerie are our favorite shops!
Great Barrington
A little bit further of a drive, about 30 min but Great Barrington has a great walkable downtown with lots of trendy shops, cafes and restaurants.
Norman Rockwell Museum
The museum is in Stockbridge, which is another quaint Berkshires town. In Stockbridge you can grab a drink or lunch at the Red Lion Inn or check out some of the famous historical homes, Naumkeag or Chesterwood.
Olivia's Overlook
If you're looking for an easy hike or just a great view point and pretty drive, Olivia's Overlook offers beautiful views of Stockbridge Bowl. On your way, you'll pass by the famous Tanglewood outdoor music venue. If you want to continue the drive, you can head into West Stockbridge and grab a coffee at Six Depot.
Mahanna Cobble Reserve Trailhead
3-mile out and back trail in Pittsfield at the ski mountain Caroline grew up skiing at. Enjoy a drink on Bousquet's deck afterwards!