Best ice cream in the Berkshires!! Plus the friendliest cows you'll ever meet.
Edith Wharton's estate is lovely for wandering around the grounds, taking in nature and admiring the art installations that have popped up during the season.
Classic nostalgia/Americana! If you're looking for some museum time, this is close by and is a very charming option.
Want to see where the statue in the Lincoln Memorial was sculpted? This is the place for you! Bonus: mild hiking around the grounds, with additional art installations to captivate and delight.
This is our favorite watering hole in the Berkshires, and the food is also delightful. Live music is available certain nights, and it's just a terrific place to hang out and chill. We may or may not have borrowed the bartenders for our event...