Black Swan Inn in Lee — Indian food on the lake, great view, kinda cramped and only Indian food, but top tier. RJs Seafood is an exquisite Italian seafood-focused restaurant in Pittsfield.

Hotel on North’s “Eat on North” also has impeccable food, all varieties, but American typical bar fare and entrees. Rem Roc’s is authentic soul food that you could take to-go and eat the best fried chicken of your life atop Mt. Greylock or the like. Treat yourself to some Ayelada frozen yogurt on the way back. If you find yourself in Lenox and starved, but don’t want to pay a mint to eat — Loeb’s grocery has a deli in back, the Earl’s Favorite is scrumptious. Chocolate Springs is worth a stop if you pass it. La Fogata in Pittsfield has out of this world empanadas, and Pancho’s on North is a solid authentic Mexican restaurant - neither have a view, but keep reading and I’ve got you covered.

Pittsfield is centrally located and you’re likely to see less traffic if you peep north of Pittsfield aka “Shire City” and much less waiting time for anything, especially food, in Pittsfield. I would steer clear of south county, Great Barrington, the Stockbridges including Lee and Lenox, if you want to stay relaxed and not up to your ears in peepers. There’s waterfalls in Dalton and lakes to drive by in Lanesborough, Pittsfield State forest area and up towards Adams.

Edit: if you’re coming from the east, take rt. 20 into Dalton/Pittsfield and go North from there. This will allow you AMAZING peeping while driving into the country, while avoiding all of South County where allllllllllllllllllllllllLLLLLLLLLLLLLL the congestion is, always. Waconah Falls should be on the way, which is a 50 yard walk to a beautiful slice of nature.