Wolf Hollow Road follows a deep gorge between the Catskill and Adirondack mountains that long served as a navigation point and passageway for Mohawk and Mohican people traveling between the Mohawk River and northern trapping and trade routes. Its steep walls enclosed a gently inclined footpath that gave Indigenous tribes an easier route, and in the 1800s European settlers adapted this well-worn path into a wagon road for hauling limestone from the Glenville hills. The route has been documented as part of Kateri Tekakwitha's flight from her Mohawk village in present-day Auriesville in 1667, and Wolf Hollow was also the site of the 1669 Battle of Kinquariones, a two-day struggle between the Mohawks and Mohicans in which the Mohawks, led by Chief Kryn, won a decisive victory and secured control of the Mohawk Valley for another century before European colonization continued the displacement of Native Americans. After the turn of the century, appreciation for Wolf Hollow's natural beauty helped inspire conservation advocacy, including articles published in 1928 and the work of Town of Glenville Historian Percy Van Epps, and preservation efforts by the Town of Glenville, Schenectady County, and the Mohawk Hudson Land Conservancy have continued as protection of the surrounding habitat and pedestrian access remain ongoing priorities. Wolf Hollow remained open to vehicular traffic until 2011, when damage from Hurricane Irene forced its closure, and as of 2025 nearly 400 acres of surrounding land had been protected from development.
