[1] The silver medal, designed by sculptor Emanuel Hahn, is a tribute to well-known Canadian humorist Stephen Leacock (1869–1944) and is accompanied by a cash prize of CA$25,000.
It is presented in the late spring or early summer each year, during a banquet ceremony in or near Leacock’s hometown of Orillia, Ontario.
In 1977 the group established an annual Student Award for Humour, which honours and encourages young Canadian writers from secondary and post-secondary levels with recognition and cash prizes for the top three.
The Leacock Award is ceremonially led by a past winner or nominee, who holds the honorary title "Mayor of Mariposa".
Subsequently, the 2011 Leacock Medal winner Trevor Cole served as the Honorary Mayor for two years with the 1993 medalist John Levesque selected to assume the post in 2025.
A jolly face represents the sun resting on waves, and the latitude and longitude of Orillia, Ontario, Canada, appear in small figures at the top.