Art on the Square is one of JWCW's principal fundraisers to support community art initiatives. 

Art on the Square is a juried show that is dedicated to providing original, high quality, handcrafted and diverse mediums of art. It is located on Duke of Gloucester and North Boundary Street in Merchants Square, Williamsburg, Virginia. The event features more than 150 artists and is free and open to the public. Proceeds from artist booth fees are donated to visual and performing arts organizations throughout the greater Williamsburg area including Williamsburg, James City and York counties.