A NEW POP-UP CASUAL DINING EXPERIENCE ON THE RACE BROOK LODGE PROPERTY SERVING FINE-CASUAL CUISINE THROUGH NOVEMBER 2025
Trailhead Berkshires is a seasonal, casual pop-up dining spot at the base of the Taconic Range in Sheffield, MA. The menu blends comfort food, trail snacks, and elevated fine-casual options, all served in a relaxed, welcoming setting. Guests can order online or at the counter, then eat anywhere on the property—inside our historic tavern, outside by the fire pits, or on the lawn with a game of cornhole. The vibe is informal, family- and dog-friendly. No reservations needed. We also offer trail snacks, supplies, and parking for visitors headed to Race Brook Falls and the Appalachian Trail. Keep an eye on the Race Brook Lodge calendar of events, including weekly “Reggae Wednesday Pool Club” and Sunday Jazz Brunch. Guests can also join the Pool & Fire Club for full access to the pool, sauna and other amenities on the property throughout the summer and fall.
TRAILHEAD HOURS
Wednesday: 4 - 7 pm (Reggae Wednesday Pool Club)
Thursday: 4-8pm
Friday & Saturday: 4 - 9 pm
Sunday: 12-4pm (Jazz Brunch)
Jazz Brunch continues with the Luke Franco Trio! This is the meanest Jazz Trio around. Enjoy food from the new Trailhead Berkshires pop-up restaurant!