Lenox has a charming downtown with some very good restaurants to choose from. My top recommendations include:
On my recent trip in July 2026, I met a friend for lunch at The Old Heritage Tavern in downtown Lenox at 12 Housatonic St. This is a casual, tavern with both indoor and outdoor seating. They have a large menu of burgers, sandwiches, wings, salads and mains including fish and chips and chicken pot pie. They also have a breakfast menu. I really enjoyed my fish and chips with sweet potato fries.
After lunch we stopped in for dessert at Patisserie Lenox. Located at 30A Church St., this is a traditional French bakery featuring a menu of desserts, pastries, croissants, macarons and breads. I really enjoyed my wildberry tart and a chai latte.
Brava: opened in 2012 at 27 Housatonic St., this is a small Tapas Bar featuring traditional Spanish tapas, pizzas, salads and cheese and charcuterie plates. On my first visit, I had a really good arugula salad, a nice scallop dish with balsamic reduction and garlic shrimp. I highly recommend it!
Alta Restaurant & Wine Bar: At 34 Church St., this Mediterranean inspired restaurant is open for lunch and dinner and features local and organic ingredients. It is considered one of the best restaurants in town.
Lenox Coffee, featuring Barrington Coffee Roasting Co., is a good spot for a caffeine hit in a charming old house. 52 Main St. Shots Cafe at 27 Housatonic St. is a good coffee spot as well along with a bakery and cafe open for breakfast and lunch. I went in July 2026 before my lunch and had a great latte.
Another fun spot is The Bookstore and Git Lit Wine Bar. This is a local bookstore with a large selection of fiction, nonfiction, classics and childrens books. They also have a wine bar which I love the name!
I recently read about Chocolate Springs Cafe at 55 Pittsfield Rd. It is a casual cafe, south of Lenox, featuring their freshly-made chocolates, cakes, gelato and other treats as well as coffee, espresso and their award-winning hot chocolate.