Pittsfield Fall Festival

Get ready to kiss your summer blues goodbye at the Pittsfield Fall Festival, where downtown Pittsfield transforms into the ultimate headquarters for seasonal excitement and unapologetic funnel-cake consumption. Held every Labor Day Weekend, this legendary gathering packs the square with thrilling carnival rides, fiercely competitive pageants, and enough local food vendors to make your diet tap out early. Motorheads can drool over the shiny classics at the Hooligan Car Show, while families enjoy the petting zoo and the show-stopping Big Parade that comes fully equipped with an epic drumline battle. Capped off with live local music and plenty of community spirit, it is the absolute best way to celebrate the changing seasons without having to lift a finger—except to hold your corn dog.