One of the Berkshires’ hidden gems is right on our venue grounds! The Race Brook Falls Trail starts directly from Race Brook Lodge and leads to a series of stunning waterfalls nestled in the forest. It’s a moderately challenging hike, but even a short walk rewards you with beautiful views and peaceful surroundings. For our adventurous friends, the trail continues up to the Appalachian Trail and Mount Race. But even a 30–45 minute round-trip to the lower falls is a perfect way to start your day.
Make a weekend of it! The South Berkshires and corners of nearby CT and NY are full of charming towns worth exploring: Great Barrington, MA Bustling and walkable, this is the area's cultural hub. Browse indie bookstores, shop boutiques, or catch a film at the historic Mahaiwe Theater. Sheffield, MA Home to our venue, Sheffield is peaceful and pastoral, with antique shops, farm stands, and the scenic Race Brook Falls trail just behind the lodge. Lenox, MA Elegant and artsy, Lenox is home to Tanglewood, stylish shops, and excellent dining. Stockbridge, MA Straight out of a Norman Rockwell painting—literally. Visit the museum, stroll Main Street, and enjoy classic New England charm. Millerton, NY Just over the border, this quaint town has a fun main street, an indie movie theater (The Moviehouse), and a great old-school spot: Oakhurst Diner. Norfolk, CT Tiny but beautiful, with an artsy spirit, gorgeous architecture, and nearby trails like Haystack Mountain and Campbell Falls.
A classic hike in the Berkshires! Monument Mountain is a favorite among locals and visitors alike. There are spectacular view facing east (great for sunrise!). Afterwards, head right out of the parking lot and you'll find yourself in downtown Great Barrington after a few miles. We love the Patisserie and/or Fuel Bistro.
While the summer season ends before October, Tanglewood remains vibrant into the fall thanks to the Tanglewood Learning Institute (TLI). Located on the Tanglewood grounds in the Linde Center, TLI presents chamber concerts and talks in an intimate indoor setting, perfect for a cozy cultural outing. Keep an eye on TLI’s fall lineup—programs often include musical gems like Schubert's Octet in F, jazz‑in‑fluenced chamber works, and performances by Boston Symphony Orchestra musicians.
Edith Wharton’s historic estate, beautifully landscaped and open for guided tours, talks, and events.
If you’re staying a little longer and feel like a day trip, we highly recommend visiting Mass MoCA in North Adams. It’s one of the coolest art museums around—huge, bold, and totally unexpected. Plus, there’s a brewery next door (Bright Ideas Brewing) and great food in the area.