The Pineland Trail Running Festival, located at Pineland Farms in New Gloucester, Maine, is a two-day extravaganza of trail races, beer drinking, barbeque, potluck salads and desserts, old timey music, and fun family events. Held annually on Memorial Day weekend the current event includes seven races with distances from 5k to 50 miles that will draw over 2,200 registered participants and about 1,500 spectators from across the US and Canada.Founded in 2006 by race directors Erik Boucher and Ian Parlin the event has undergone a number of transformations prior to its current configuration. From 2006 to 2007 the event included a 25k and 50k race held on Sunday and was called the Pineland Farms Trail Challenge. Then in 2008 a 4k canicross and a 50 mile race was added. In 2010 a second day of races was added and the event was renamed the Pineland Farms Trail Running Festival. Starting that year the 5k (with shoes), Barefoot 5k, 5k Canicross (with dogs), and 10k race was held on Saturday, and the 25k, 50k, and 50 miles races were held on Sunday. In 2013 the event was renamed the Pineland Trail Running Festival.
In 2012 Runner’s World magazine named the Barefoot 5k the Best Barefoot Event in the country. It is believed that the Barefoot 5k and 5k Canicross races are both the largest competitive and sanctioned races of their types in the United States.