Trail Running calendar near Annapolis 2026-2027
We have found 107 Trailruns within 80 miles of Annapolis. See below where and when you can find the races.
We have found 107 Trailruns within 80 miles of Annapolis. See below where and when you can find the races.
HAT Run 50K in Havre de Grace, MD on March 21, 2026 is a 50K trail race with nearly 4,400 feet of climbing, a 3 mile start loop and two 14 mile loops, and four stream crossings that may result in wet feet.
Join The Husky Run 5K on the scenic Ma and Pa Trail in Bel Air. This walk and run event is open to all ages and abilities. Every finisher earns a limited-edition Husky medal.
On March 29, 2026 in Severna Park, MD runners can choose a Marathon or Half Marathon mostly on the asphalt B&A Trail. USATF certified courses, staffed aid stations, finish medals, and participant quarter zips are provided.
Montchanin Trails 5K is a trail run in Wilmington, Delaware on March 29, 2026. The course uses single track trails, fields and gravel roads on private property with access and social media rules; the event is limited to 300 runners and incl..
A 50 mile trail run near Clifton, Virginia that follows forested, rolling terrain along Bull Run and the Occoquan River. The 2026 race is the 32nd running and features large bluebell stands and a Civil War theme.
A three-loop 5k at Molon Lave Winery in Warrenton, VA on April 4, 2026, run as a cross country route with two water stations and chip timing. The race counts toward multiple series and offers a virtual option.
A 14-mile untimed point to point trail run in King George, Virginia following the Dahlgren Railroad Heritage Trail. The cupless event features themed aid stations, shuttle service, practical finish swag and supports Sheetz For the Kidz.
Join the Turtle Derby, a turtle themed 5K on brewery trails supporting Susquehannock Wildlife. Enjoy a wooden finisher medal, costume contests, awards, live music and on site beer.
Experience a scenic 5k atop a ridge in apple country with cross country terrain, orchard views and a post race wine pour. Family friendly with virtual options, the event supports Nik's Wish and offers fun keepsakes for finishers.
A 100 mile ultramarathon on the C&O Canal towpath near the Potomac River. The course is one 40 mile loop plus two 30 mile loops with multiple aid stations and low elevation terrain. WSER 2027 qualifier.