There’s a ton of great places to eat in Pittsfield. It’s leaf peeping season, so Pittsfield state forest, Lanesborough has a great lake, take a drive up Mt. Greylock, or go to Waconah Falls. Eat on North has great fare, soul food at Rem Rocs, RJ’s seafood has exquisite Italian food, Teo’s is a local dive hot dog stand, cash only, La Fogata has empanadas that are life changing, as well as the arroz con pollo, Papa Joe’s pizza and cannoli are great. There’s hourly kayak and rowboat rentals on Lake Onota. Ayelada is a local froyo place or Chocolate Springs down the road if you want a decadent sweets experience.