Prince Frederick
Trail Running Calendar near Prince Frederick 2026-2027
Explore the top trail runs near Prince Frederick for 2026-2027! We've gathered 7 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A scenic chip timed 5K at Running Hare Vineyard on October 11, 2026 with a complimentary drink for those 21 plus and post-race music and photos.
November 2026
Trail races of 50K and 20K through the single-track woods of Rosaryville State Park near Upper Marlboro, MD, organized by the Annapolis Striders with limited field and aid stations.
February 2027
Loop trail races at Saint Marys Lake near Leonardtown, MD offering 17K, 34K, and 50K options with marked trails, aid stations, and on-course support.
April 2027
Runs through 50 acres of vineyards at Ingleside Vineyards with 5K and 8K chip timed courses, plus post race wine and live music.
A chip timed 5K run/walk at Corteau Vineyards on a two lap grass course through the vines, with race swag, a wine pour and proceeds supporting ZERO Prostate Cancer.
May 2027
Chip-timed 5K at Running Hare Vineyards with post-race wine, live music, shirts and finisher glass; walkers and children are welcome.