The Prairie Whale

Nestled in a scenic meadow, this seasonal roadside shack serves up gourmet burgers and sandwiches alongside lawn games and picnic tables for a perfect casual dining adventure.

Nestled in Great Barrington, the Mahaiwe Performing Arts Center is a charming 1905 theater offering an intimate vibe and stellar acoustics for everything from classic films to live performances.

Westerlind merges rugged outdoor gear with chic, stylish clothing, offering a unique selection of high-quality pieces for the fashionable adventurer.

A serene riverside park with a short, easy trail, scenic views, benches, and historic plaques perfect for a peaceful stroll.

Bernay Fine Art in Great Barrington is a vibrant gallery showcasing a diverse mix of contemporary artists in a relaxed, welcoming atmosphere.

For over 40 years, Guido's Fresh Marketplace in the Berkshires has been the go-to spot for local, high-quality produce, meats, and gourmet offerings, where the friendly staff ensure a delightful shopping experience.

BOBA TRAIN in Great Barrington serves creamy milk teas, fresh fruit smoothies, aromatic coffee, and vegan boba in a cozy, welcoming spot.

Familiar Trees is a cozy gem in Great Barrington, blending vintage and contemporary books on art, design, and more with an eclectic selection of decorative objects.

In a chic old bank, this foodie haven offers 125+ curated cheeses, charcuterie, wines, and gourmet bites for true flavor explorers.

Pixie Boulangerie is a cozy spot dishing up flaky croissants, rustic breads, and seasonal pastries with authentic French flair.