On November 19, 1916, at about 2 a.m. on a dark, cold night, a devastating fire swept through Roscoe, destroying 23 buildings, including eight prominent business places and ten or eleven other structures, with losses estimated above $150,000 and insurance covering less than a third of that amount. The fire began in the bowling alley building owned by Frank H. Mauer of Liberty, and although its cause remained unknown, reports of an explosion led to belief that a coal stove may have exploded. Wesley Sipple and his mother, trapped above the bowling alley when the lower floor was already ablaze and the stairway cut off, escaped by jumping from a front window, and his mother broke her leg at the ankle when she struck the sidewalk. Firefighters quickly stretched hose to a hydrant near the hardware store and at first thought the blaze was under control, but failing water pressure left them unable to stop its spread as residents hurried goods from neighboring buildings farther and farther down the sidewalk. More than a hundred men in Livingston Manor gathered ready to help, but the O and W railroad refused to send a special train despite having crews and equipment available, so the men instead collected automobiles and wagons and came to Roscoe, joined by helpers from Liberty. Though little could be done without water, Roscoe credited the men of Livingston Manor and Liberty, especially the Manor boys, whose efforts saved the Maus house and likely also the Presbyterian church and other buildings.