Wilna Hervey & Nan Mason are a same-sex couple who lived in Woodstock, one of the few American communities where they could feel comfortable in the early-mid 20th century. As artists, Hervey, a former actress known for her tall stature, and Mason, whose father worked on stage with Hervey, evolved into accomplished and imaginative talents, exploring a wide variety of genres over the course of their long careers. Seven years after the Maverick Festival was forced out of commission, the couple picked up the reins, renaming it the Full Moon Costume Picnic. They kept the festival alive from 1938 to 1962, paving the way for the Woodstock Festival of 1969.

Created for the Maverick Concert Hall's centennial in 2016, Stephen Blauweiss' short film Music in the Woods covers the history of the Maverick Concert Series in Woodstock, presented by curator Susana Leval, in association with an art exhibition held at the Woodstock Artists Association & Museum (WAAM) in partnership with Byrdcliffe. The film also covers Hervey White himself and the history of the iconic horse sculpture by sculptor John Flannigan, a memorable feature of the concert hall.

Ze'ev Willy Neumann creates sculptures out of wood. This film documents his Love Knot project, which used 40 sheets of plywood and took a year and a half to complete. The premise is to link two neighboring towns in upstate New York—Woodstock and Saugerties—via identical sculptures to help bring the towns closer by encouraging each town to visit the other. He designed these love seats as a knot in the shape of a heart, incorporating the infinity sign. Visitors are encouraged to see both. "To bring forth the idea of conceptual art is a wonderful way of actually translating a daily object into a story," says Neumann.

In this day and age, as we easily record videos on pocket-sized devices, we stand on the shoulders of the Video Freex who led the way using large, bulky, and primitive analog technology. Before there was cable television, there was pirate television, which was pioneered by Video Freex, whose origins date back to the 1969 Woodstock Festival. The Freex settled in the tiny hamlet of Lanesville, just outside Phoenicia in Greene County. At a time when most people didn't have access to any video equipment, the Freex captured everything from the most mundane aspects of daily life to important national events. As member Bart Friedman commented while roaming around with their "Lanesville TV Newsbuggy" looking for action, "sometimes [you get] peanuts and sometimes shells." The group developed educational projects for children and created one of the first ever museum exhibitions of video art. They documented social events such as the May Day protests against the Vietnam War in Washington DC which took place from May 3–5, 1971 and led to the largest mass arrest (12,000 people) in U.S. history.

Elliot Landy is best known for his iconic photographs from the 1960s classic rock period, including at The Filmore East in Manhattan and the Woodstock Festival in Bethel. He began his photographic career working with the underground newspaper The Rat in support of the rising tide of anti-war sentiment during the late '60s. His press pass and camera not only gave him access to the political scene but also provided him a personal entry into the new rock music counterculture, capturing Bob Dylan, Janis Joplin, The Band, Jimi Hendrix, Jim Morrison, Eric Clapton, Jefferson Airplane, Santana, Frank Zappa, John Lee Hooker, and many others.

The 212 project ran summer retreats from 1967 to 1969 in the old Holiday Country Inn midway between Saugerties and Woodstock on Route 212. It was briefly home to professionals in the visual arts, music, performing arts, filmmaking and sciences. The collective fostered a collaborative meeting point and simplified time and space constraints for the participating artists. It encouraged them to experiment with the diverse new media and helped them to explore and synthesize the exploding potentials then being articulated through happenings, expanded cinema, environmental music, and multimedia theater, dance and sculpture.