The Brookside Art Annual is a three-day outdoor art show held on the first weekend of May in the historic Brookside Shops, in the center of Kansas City. It is the city's first outdoor art show of the year and has run for 40 years, with its 40th anniversary in 2026. Nearly 180 artists from across the country are chosen through an extensive jurying process. They show work in over a dozen mediums, from jewelry and painting to clay and photography. The show is consistently ranked among the top twenty-five art shows in the United States by Art Source. Each year it names a featured artist whose work appears on commemorative posters, shirts and cards, and it presents awards such as the Virginia Kellogg Best of Show. Alongside a variety of activities, its stated focus is the art.