From the early 20th century until today the  Woodstock Art Colony attracted a diverse group of artists to both experiment and work in various styles of the visual and performing arts. The artistic colonization of Woodstock started with the  Byrdcliffe art colony in 1902, which included facilities and studios for artists to participate in the decorative arts, fine arts, and print making, with instructors. Writers and musician and performers also came to the Woodstock area with the birth of the nearby Maverick community, which had some of the first festivals and concerts. Started in 1915 they included a performance of the Metropolitan Orchestra, festivals, plays, and avant-garde events. 

The Arts Students League, a very important art school  based in New York, attracted more than 200 art students in the area starting in 1906, when it moved its summer school to Woodstock attracting a variety of artists and teachers.  The Woodstock Artists Association started in 1919 as a venue for exhibits. The facility and association is active today.  

By the 1920s, the Woodstock Art Colony was entrenched in the hills and village of Woodstock and surrounding areas.  The establishment of this artists hub attracted many famous artists, including Milton Avery, George Bellows,Richard Diebenkorn and Yasuo Kuniyoshi. Many were experimenting with abstraction, cubism, modernism, figurative art, and the in-born multi artistic enthusiasm of this Catskill region.