Sleepy Hollow may make its bones on Halloween, but it and its sister village Tarrytown light up on other holidays, too. Case in point: the annual Winter Stroll in both downtowns, with extended shopping hours, Christmas decorations and light displays, carolers, ugly sweater contests, and much more. Ride the free Holly Jolly Trolley between both villages and enjoy seasonal food and drinks from local restaurants and bars. And check out our recent guide to Tarrytown and Sleepy Hollow to see what else there is to do in the area.