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.

Bethel Woods Center for the Arts, which also includes a museum of the sixties and Woodstock, holds many concerts and other events throughout the year.

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 theater company focusing on experimental work in Highland Lake, and the Delaware Valley Arts Alliance (DVAA).

Delano-Hitch Stadium in Newburgh has played host to various professional and amateur baseball teams from various leagues since opening in 1926. The stadium is currently home to the Newburgh Newts.

The state parks include Goosepond Mountain State Park, Harriman State Park and Sterling Forest State Park. It is also the location of Orange County Choppers, the custom motorcycle shop featured on The Discovery Channel television series American Chopper.