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.

Trail races at Codorus State Park near Hanover, PA, featuring 8 Miler, 25K, and 50K looped courses on the Ranger Trail with singletrack, horse trails, hills, mud and variable March weather. Aid station at Mile 8 and proceeds support a local..

A trail race at the Workhouse Arts Center in Lorton on March 15, 2026, offering mostly singletrack through forest and meadows with options of roughly 5.4 miles or 10 miles. The event includes aid stations, optional medals, a kids program, a..

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.

UTMB Index

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

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.

Join Washed Clean in York PA for a fun trail 5K, 1 Mile Walk, and free Kids Fun Run with a foam finish and bumpy scenic course around Genesis Church. Family friendly with strollers welcome and proceeds benefiting local nonprofits.

Trail races at Rosaryville State Park in Upper Marlboro MD on March 28, 2026 include half marathon, 10K and 5K plus virtual options. Courses run through hardwood forests, fields and equestrian trails with multiple aid stations.

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..

April 2026

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.

The Trail Demon 10k is a technical trail race on a forest loop at Dirt Farm Brewing in Virginia. Runners receive a finisher medal, a tech shirt, and a post race beer. Proceeds support the Boulder Crest Foundation for veterans and first resp..

Trail races of 5K and 10K take place at ThorpeWood private property in Thurmont, Maryland on April 4, 2026. Both are part of the FSRC Grand Prix, chip timed, with marked loops, on-site water and designated parking.

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.

A memorial trail event at Piney Run Park offering 50K, 25K, a 5.25 mile race and an 8 hour challenge on a 5.25 mile loop with aid stations and awards for top finishers.

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.

Run through the scenic vineyards of Barrel Oak Winery on a challenging cross-country course with hills and gravel paths. Runners receive a finisher's medal, tech shirt, and a glass of wine, with proceeds supporting veterans. A virtual optio..

A trail race at Lake Fairfax Park in Reston on April 19, 2026 offering 5.1 mile and 10 mile singletrack courses with short technical sections and lake views. Aid stations, post race food, optional finisher medals, and a kids program are ava..

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.