Taking place in 1969, this film draws inspiration from the true story of Elliot Tiber, a hopeful interior designer from Greenwich Village. His parents, Jake and Sonia, own the dilapidated El Monaco Resort situated in the quaint town of Bethel, New York. Amid financial difficulties, they face the possibility of losing their establishment, particularly as a hippie theater group called The Earthlight Players struggles to meet their rental obligations. In an emotional plea, Elliot urges a local bank to refrain from foreclosing on their mortgage, while his mother launches into a heartfelt monologue about her tribulations as a Russian refugee. The family has until the summer ends to remedy their situation.
In a bid to turn fortunes around, Elliot devises a plan to organize a small music festival. He manages to secure a permit for just one dollar from the town's chamber of commerce, an organization he also leads as president. When he catches wind that the Woodstock Festival organizers are encountering obstacles at their initial location, he promptly offers them his permit along with the accommodations at the motel. Michael Lang, one of the organizers, gratefully accepts the offer. Additionally, local farmer Max Yasgur provides nearby land for the event. Initially agreeing on a fee of $5,000, they later renegotiate it to $75,000 upon recognizing the scale of attendance, a decision that is met with some reluctance.
While Elliot finds common ground with Yasgur regarding the motel fees — especially after Sonia's initial resistance subsides following an upfront cash payment — they both encounter significant local pushback. The diner refuses to serve Elliot, local inspectors target his motel for violations, and some youths disfigure the property with hateful graffiti. Yet, as the festival approaches, tension gives way to an influx of peace, love, and commerce, enriching the Tiber family in the process.
An unexpected addition to their team, a cross-dressing Korean War veteran named Betty von Vilma, is hired to maintain security during the festival. Meanwhile, Elliot faces his own struggles, particularly concerns about concealing his homosexuality from his family, while he develops feelings for one of the festival organizers residing at the motel.
As the rock concert unfolds, Elliot, alongside his father and Vilma, hears the distant sound of music. His father, revitalized by the newfound energy in Bethel, encourages Elliot to attend the concert. Riding on the back of a compassionate state trooper's motorcycle through the buzzing traffic, he finally arrives at the event. There, he meets a free-spirited couple who invite him for an LSD experience in their VW Bus. Initially uneasy, Elliot eventually succumbs to the psychedelic atmosphere, emerging under the mystical glow of the festival after sundown.
Returning home, he shares breakfast with his parents and suggests the idea of replacing him now that financial burdens are lifted, but his mother finds it too painful to entertain such a notion. Following another festival day filled with joy, during which his friend Billy, a Vietnam veteran, begins to heal from his trauma, Elliot discovers his parents in a fit of laughter after consuming Vilma's hash brownies. The previously strained family dynamic transforms into one filled with love and joy.
However, the next morning reveals a secret; Sonia discloses that she has secretly hoarded \$97,000 beneath the floorboards. Displeased that his mother hid such a substantial sum while he exerted effort to alleviate their struggles, Elliot resolves to head to California. As he packs his things, he states heartfelt goodbyes to his father, who supports his decision to pursue independence. In a final visit to the festival's site, Elliot reflects on the muddy aftermath of the concert, where Lang rides by on horseback, and they share a moment of gratitude for the event's success, with Lang hinting at his ambitious future project—hosting a free concert in San Francisco featuring The Rolling Stones.
