Downtown Pittsfield, Inc. (DPI) will be facilitating a Holiday Downtown Pittsfield Passport giving shoppers a chance to win one of three prize packages made up of donations from the 40 participating local businesses. The grand prize value will be over $500. The promotion will run Friday, November 24 through Sunday, December 3 and will encompass Black Friday, Small Business Saturday, and DPI’s Festive Frolic (December 1-3). See the Event Website for details on how to participate.