Start from 38 curated places around Lenox, MA, then choose the recommendations that fit your guests.
Restaurants & cafés
Alta Restaurant & Wine Bar
A long-running Lenox anchor that pairs Mediterranean-inspired cuisine with one of the most serious wine programs in western Massachusetts — nine pages of bottles and 24 wines by the glass. Organic local ingredients, goat cheese mousse with beets, cider-braised pork cheeks, and roasted chicken paella keep regulars returning season after season. A natural choice for celebrating something.
Bistro Zinc
A Lenox institution whose Church Street dining room — tiled floor, tin ceiling, mirrored walls, red banquettes — could have been lifted straight from a Paris side street. Boeuf bourguignon, coq au vin, steak frites, and a classic onion soup are done with real care. One of the most reliably satisfying dinners in the Berkshires.
Trails & outdoors
Trail of the Ledges — Pleasant Valley Wildlife Sanctuary
The premier hike in Lenox and among the best in the southern Berkshires — a 2.8-mile round trip with 938 feet of elevation gain up Lenox Mountain through the Mass Audubon sanctuary. The ledge views near the summit reveal Mount Greylock, the Taconic Range, and on clear days, the Catskills. Rated 4.7 stars by over 760 AllTrails reviewers.
Kennedy Park Trail Network
A 15-mile network of multi-use trails spread across the town conservation land on the hill above downtown Lenox, accessible on foot from Church Street in minutes. Hikers, trail runners, mountain bikers, and cross-country skiers all use the same well-groomed routes through mixed hardwood forest. The loop past the old Aspinwall Hotel ruins is the most historically interesting route.
Things to do
Tanglewood Music Festival
The crown jewel of the Berkshires summer — the Boston Symphony Orchestra's summer home since 1937, running from late June through August with a season of 100-plus performances. Main stage concerts in the Koussevitzky Shed, chamber recitals in the intimate Seiji Ozawa Hall, the popular popular-artist series, and student showcases from one of the world's great music academies all happen across a single magical campus.
Shakespeare & Company
Founded in 1978 and now one of the most respected Shakespeare companies in the United States, operating a campus with three performance spaces including an outdoor Roman Garden Theatre. The summer season runs Shakespeare alongside contemporary plays and new works, and the company's approach — physical, passionate, and populist — makes even the tragedies accessible to first-time theatergoers.
Landmarks & sights
Tanglewood
The summer home of the Boston Symphony Orchestra since 1937 and the spiritual center of the Berkshires summer season. The 524-acre estate holds the grand Koussevitzky Music Shed, the intimate Seiji Ozawa Hall, and rolling lawns where thousands spread picnic blankets and listen under the stars. Beyond BSO performances, Tanglewood hosts the popular artist series and the Tanglewood Music Center's student concerts.
The Mount — Edith Wharton Estate
Built in 1902 by Pulitzer Prize-winning novelist Edith Wharton, The Mount is a National Historic Landmark where the author spent her most productive years writing 'The House of Mirth' and 'The Age of Innocence.' The grandly restored mansion, formal terraced gardens, and surrounding woodlands reflect Wharton's philosophy that architecture and landscape should be inseparable. Book talks, outdoor theater, and lectures fill the summer calendar.