The first Covered Bridges Half Marathon was first held in 1992 along some of the best running routes around Woodstock, Vermont. The course is unique because of the four covered bridges along the way, two of which the runners ran through. Like many races, the course was adjusted several times in the first few years to address traffic and parking concerns, as well as the growing popularity of the race. The current course has been in place since 1997. The popularity of the race has continued to rise, reaching 2,900 registrants in 2001, but has since been scaled back to the present cap of 2,300 runners. The on-line registration fills quickly each year, usually in a few minutes from the time that it “goes live.”

The race is organized by a completely volunteer staff, under the corporate umbrella of CBHM, Inc., a non-profit corporation formed specifically to organize running events and donate the proceeds to charity.