The fair was first established in 1954 when two young antiques dealers, John Bihler and Henry Coger, suggested the creation of an antique show-fundraiser for East Side House Settlement to the charity's co-director Grace Lindquist. Their proposal came days after socialite Norris Harkness enlisted Lindquist's help to sell five
Louis Vuitton trunks at the National Antiques Show, during which time Bihler and Coger witnessed Lindquist's acumen for antiques. On Monday, January 24, 1955, the fair opened at the Seventh Regiment Armory with one hundred dealers from the East Coast. By the end of the decade, The Winter Show was seen as the leading event of its kind in the United States. In 2018, Helen Allen was appointed The Winter Show's Executive Director. Michael Diaz-Griffith is the Show's Associate Executive Director. In 2025, The Winter Show will return to the Park Avenue Armory to celebrate its 71st year. ==Loan exhibitions==