Trailhead Berkshires

Trailhead Berkshires is located at Race Brook Lodge on Route 41 in Sheffield, MA, between Salisbury, CT and South Egremont, MA.

 

Dear friends, Race Brook Lodge will be closing permanently at the end of November 2025. Please join us sometime in November for a final visit! We have some fantastic events planned for the final month, including a special Thanksgiving buffet dinner and a Holiday market on the final weekend. We will keep the campfires roaring right up to the end! Our family has been honored to steward this land since Dave first landed here in 1990, and now the time has come for a new chapter here. We have put the property up for sale and we are hoping to find a buyer who will care for the property in a way that is respectful to the land and our local community. Please reach out if you have any ideas. In the meantime, after November 30th, we will be offering long-term residencies, some events and pop-up dinners in the tavern until a sale is confirmed. With much Love & Gratitude for over 30 years of hospitality…. Sincerely, Dave, Casey & Saadia.


A POP-UP CASUAL DINING EXPERIENCE AT 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.


MENU & ONLINE ORDERING
Trailhead Info & Links

TRAILHEAD HOURS

Thursday—Saturday: 4-9pm
Sunday 11-3pm: Jazz Brunch

Open at other times for special events



Events coming up at Race Brook Lodge (click for full schedule)