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 North Boundary Street from Richmond Road to Scotland Street, Williamsburg, Virginia. The event features 90 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. Raffle tickets, 2023 commemorative posters, and posters from past years will be available at the JWCW tent at the intersection of Prince George and North Boundary Streets.