Bear Hill is a mountain in Ulster County, New York, south of Ellenville near Cragsmoor, identified with the Shawangunk ridge system though sometimes described as part of the Catskills. Framed by nearby peaks such as Losees Hill and Mount Meenahga, it sits within a landscape closely tied to the hamlet. Much of the mountain is protected within the privately managed Bear Hill Preserve of the Cragsmoor Association, which allows public access for hiking and picnicking for a fee. Known for broad views and the demanding Grapefruit Squeeze trail feature, Bear Hill is valued chiefly as a preserved natural area reflecting Cragsmoor’s tradition of stewardship and access.