The Town of Roxbury is at the eastern end of the county.
The town was the birthplace and the home of naturalist John Burroughs. A memorial site has been placed by his birthplace. Jay Gould, the Railroad financier, was also born in the town. The Main Street Historic District includes the Jay Gould Memorial Church and was listed on the National Register of Historic Places in 1988. Other sites on the National Register of Historic Places include the First Old School Baptist Church of Roxbury and Vega Cemetery, Isaac Hardenbergh House, Second Old School Baptist Church of Roxbury, Walter Stratton House, and Ulster and Delaware Railroad Depot and Mill Complex.
Author Walter R. Brooks was a resident. He began visiting Roxbury in 1937 and he and his wife Anne moved to a home on Main Street in 1948, where he lived until his death in 1958. He wrote a number of books while in Roxbury, including many titles in the popular "Freddy the Pig" series.