It's 1969, and Elliot Teichberg (DEMETRI MARTIN) is a young man who works and lives in New York City, but helps his immigrant parents, Sonia (IMELDA STAUNTON) and Jake (HENRY GOODMAN), run their dilapidated El Monaco Motel in the small town of Bethel, New York. When not trying to help his friend, Billy (EMILE HIRSCH), who's returned from Vietnam a troubled young man, Elliot also serves as the president of the chamber of commerce.
There, he presides over local permit hearings, such as for Billy's brother, Dan (JEFFREY DEAN MORGAN), while also organizing summer fine arts events in the town, including the Earth Light Theater troupe and its lead actor, Devon (DAN FOGLER). In that role, Elliot comes up with an idea that he believes will not only boost the fortunes of Bethel, but also his parents and their mostly vacant motel.
After hearing that a nearby town has turned down hosting a music event that might draw thousands, Elliot decides to invite them to Bethel, and soon escorts the promoters of the Woodstock Music & Art Fair -- including Michael Lang (JONATHAN GROFF), Tisha (MAMIE GUMMER), and their money men -- over to a nearby dairy farm run by Max Yasgur (EUGENE LEVY).
After some negotiating, the venue is set, with both the musical acts and the number of expected spectators growing each day. As the likes of construction worker Paul (DARREN PETTIE), Reverend Don (RICHARD THOMAS) and former Marine turned transvestite Vilma (LIEV SCHREIBER) show up to help with the three days of peace and music, Elliot tries to keep things running as smoothly as possible, all while finally beginning to break out from under his overbearing mother.