Music performances include Kristoffer Andrew Ross: Castle Street Corner, Madison and friends: Rubiner's Cheesemongers, Jaane Doe: Triplex Courtyard, Berkshire Hills Chorus: First Congregational Church, and Sherry Steiner: Carr Hardware.

Main Stage Raillroad Street music performances include Greg Glassman Band: Lower Railroad Street and Michael Lesko & Suns: Upper Railroad Street