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Sullivan County has been a popular vacation spot since the 19th Century, with mountain climbing, boating, and other outdoor activities, and the Monticello Raceway being among the attractions. The majority of the tourism occurs in the summer months. It was the site of the hundreds of resort complexes of the Borscht Belt (with their golf courses, social events, and entertainers), between the 1920s and 1970s. It was the site of the 1969 Woodstock Festival.

Other notable cultural destinations include the CAS Arts Center, a multi-arts exhibit space and education center run by the Catskill Art Society in Livingston Manor, New York, the NaCl Theatre, a professional regional theatre company focusing on experimental work in Highland Lake, New York, and the Delaware Valley Arts Alliance (DVAA) in Narrowsburg NY, which offers two art galleries, performing arts and cultural programming, grants for artists and nonprofits, Big Eddy Film Festival and Riverfest.

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