Paint Webster is a plein air outdoor painting competition held on the second Saturday in May. Open to both amateurs and professionals, the competition encourages artists of all ages to capture on canvas the outdoor spaces of the charming Webster Groves community. At the end of the day, artists can submit their works to compete for more than $2,200 in awards. A reception is held for the community to meet the artists and view the paintings. Artists can have their works hung at the Old Orchard Gallery, in Webster Groves, for the week following the event.