Trail Running calendar near Annapolis 2025-2026

We have found 57 Trailruns within 80 miles of Annapolis. See below where and when you can find the races.

Devil Dog Ultras in Prince William Forest Park offers 50K, 100K and 100 mile trail loops on well marked single track and rolling fire roads. Expect staffed aid stations, limited bunkhouse beds and a lively winter ultrarunning weekend.

Join the Fall Backyard Burn at Fountainhead Regional Park for scenic trail running around the Occoquan Reservoir with shorter and longer course options. Post race food, music and charity support add to the fun.

The Founders Half Marathon in Potomac on December 14 showcases a scenic 13.1 mile out and back along the C&O Canal Towpath and serves as race two of the DCRR Snowball Series. USATF certified with post race snacks and online registration.

Join the Anniversary Run 15K at Quiet Waters Park, a scenic trail race that wraps up the Annapolis Striders Championship Series. Finish at Sassafras Pavilion for awards, a lively community vibe, and volunteer opportunities.

January 2026

Join the Food for Others 5k and 10k at Leesylvania State Park on Jan 17, 2026 for scenic trail and paved sections, small hills, and a festive finish with tech shirts and medals. Proceeds benefit the charity and a virtual option is available..

Angela Ivory Memorial Trail Races at Killens Pond State Park on Jan 24 and 25 offer ultra distances including 50k, 100 mile and 24 hour events. The 50k is full with no wait list; enter another distance and drop in on race day if spots open.

Run the Mid Maryland Trail Festival at Rockburn Branch Park in Elkridge, MD, a scenic 50K on wooded trails made up of six loops of about 5.18 miles each. Solo runners or teams up to six can tackle the full distance or share loops in a relay..

Take on the Dahlgren Trail Half Marathon on January 31, 2026 in King George VA, a flat and scenic out and back along the Dahlgren Railroad Heritage Trail ideal for a fast, enjoyable run. All finishers earn a custom medal and well spaced aid..

February 2026

Run a timed trail ultra at Little Bennett Campground on scenic 4.4 mile loops, choosing 5 or 9 hour solo or relay challenges. Enjoy aid stations, Altra shoe demos, a long sleeve race top and a post race chili bar while supporting Montgomery..

Take on a technical trail at Paradise Springs with rocky riverside singletrack in 5k or 10k. Finishers get a medal, technical shirt and a glass of wine while supporting the John P. Mayhugh Foundation.

Run scenic laps around Saint Marys Lake and through Salem Forest in Leonardtown, MD, choosing 17K, 34K, or 50K. Rugged single track, forest roads, and lakeside trails offer technical fun and a small, friendly field for a low key trail day.

March 2026

Run scenic but technical forest loops at Conway Robinson State Forest on March 7, 2026 with 5k and 10k options plus a virtual race. Support Lost Dog and Cat Rescue and earn a finisher coin, tech shirt and chip timing.

Test your limits at the Dark Side 8 Hour Ultra in Little Bennett Park, Clarksburg. You have eight hours to run as many 5.5 mile loops on scenic single track trails as you like, with hearty on course aid and a post race meal to refuel.

Tackle the MCRRC Seneca Creek Trail Marathon or push on to the 50K in scenic Seneca Creek State Park. Expect hilly muddy rocky single track and a choose your distance finish for a customizable trail challenge.

No Man's 50K is a women only trail race in Triangle, VA offering 50K and 25K across two scenic 15 mile loops. Limited to 120 entrants, the course is mostly single track with stocked aid stations.

Join the Smoketown Brewery 5k and 10k on March 8 for flat gravel out and back routes, with a virtual option and walkers welcome. Finishers get a medal, tech shirt, chip timing and a beer while supporting Wear Blue Run to Remember.

Blazing Saddles at Codorus State Park on March 14, 2026 offers 8 mile, 25K and 50K trail loops over singletrack and horse trails with runnable hills, mud, and possible snow. Proceeds support a local animal rescue.

Tackle the HAT Run 50K in Havre de Grace, Maryland, a scenic trail challenge with rolling single track, open fields and nearly 4,400 feet of climbing. Expect stream crossings and a rewarding day on rugged, looped trails.

UTMB Index

Test your endurance at the Genesee Valley Ultra, a timed loop on scenic farm roads where runners log as many 2.5 mile laps as they can in 6, 12, or 24 hour events. Solo runners and relay teams are welcome for a fun, competitive challenge.

Last Runner Standing action at the Capital Backyard Ultra near DC on March 28, 2026, with runners repeating a 4.167 mile loop each hour until one remains. Silver Ticket, 60 spots, $1,000 prize and finisher award.