In the late 1890s, this building served as a rooming house for workers in the mills of Sloatsburg until around 1950. Around 1904, Henry and Kathleen Tobin converted the ground floor into a restaurant that offered open-air dining on a large veranda-style porch as well as an elegant main dining room. The Glenwood prospered as a fine-dining restaurant for nearly fifty years, until the opening of the NYS Thruway diverted travelers away from Orange Turnpike.