My favorite town in the Berkshires is Great Barrington. It is a quintessential New England town with a hippy edge and history. If you’re starting with lunch, you should really check out the Gypsy Joynt Café, come for the ambiance and stay for the food.
This is a mystical place and the eclectic decorations may make you want to sit inside even if the sun is shining. If you come on the right day, you might even find a band playing some live music. The food is what will complete the experience at this joynt. Their focaccia is baked daily, and it is so darn good. Get a sandwich, you won’t be sorry. If you’re feeling really good, enjoy one of their delicious frozen margs.
Walk off some of that meal on the Housatonic River Walk, a short jaunt with some lovely scenery.
Learn a bit of history on the way about W.E.B. Du Bois, an early civil rights activist who lived in Great Barrington.
Enjoy popping in to all of the interesting stores, and just walking around town wishing you lived here.
Make sure to end your trip with some ice cream from SoCo Creamery, you can’t get it in the Capital District. With flavors such as banana brownie and Mexacali Chocolate you may find yourself wanting to visit the Berkshires more often.
Go! Enjoy Great Barrington! I know I did.