Trail Running calendar near Annapolis 2026-2027

Test your limits on this timed trail ultra at Little Bennett Campground with 5 and 9 hour solo and relay options on a scenic 4.4 mile loop. Enjoy aid stations, Altra demos and a post race chili while supporting Montgomery Parks Foundation.

Looped trail races at Killen's Pond State Park offering 50K, 24 hour and 100 mile options on an about 3.1 mile dirt loop with low technical difficulty and limited support.

A trail 5 km and 10 km run through Manassas National Battlefield with chip timing, finisher medal, technical shirt, and a virtual race option. The event benefits the Manassas Battlefield Trust and starts and finishes at the Winery at Bull R..

A seven mile trail race at Cromwell Valley Park featuring rolling hills, fire roads, fields and single-track trails, with post-race food and beer and proceeds supporting the park and Talmar’s therapeutic programs.

Celebrate Valentine’s Day with a fun and friendly 5K at Kinder Farm Park in Millersville on Feb 14, 2026. Enjoy a mostly flat loop with gentle hills, chip timing, and awards for top finishers in a welcoming community race.

Hit the forest trails in Parsonsburg for the 4STEPS Therapeutic Riding 5K on Saturday, February 21, 2026. Enjoy a scenic first time 5K through Wicomico Demonstration Forest while supporting therapeutic riding programs for riders with specia..

Trail races in Columbia, Maryland along the Little and Middle Patuxent Rivers, offering 5K, 10K and half marathon distances with start and finish at the Guilford Pratt Truss Bridge. Registration includes a long sleeve shirt, finisher medal..

A club-based 10 miles race in Columbia, MD where runners score points for their RRCA club; awards are given by club and the event is part of the Maryland RRCA Grand Prix series.

Trail 5k and 10k races at Paradise Springs and Hemlock Overlook Park with series points, chip timing and a post race glass of wine. The 10k is two laps of the 5k technical route with multiple water stations.

Trail races near Leonardtown, MD on an ~10.5 mile loop around a 250 acre lake, offered as 17K, 34K, or 50K with two aid stations and a 100 runner limit.

Run a scenic 50 km trail at Hashawha Environmental Center near Westminster MD on Feb 28, 2026, featuring rolling hills, stream crossings and two big loops. Expect runnable single track, ample climbing and warm post race hospitality.

Trail races of 5 Miler, 10 Miler and a two person 10 Miler relay take place at Rockburn Branch Park in Elkridge on March 1, 2026; a portion of proceeds supports Bigfoot Endurance for Parkinsons research.

On March 1, 2026 at Wakefield Park in Annandale, the Spring Backyard Burn offers 5.5 mile and 10 mile trail race options across singletrack, doubletrack, stream crossings and minimal pavement. The event features aid stations, post race food..

A 31 mile trail event at Rockburn Branch Park in Elkridge Maryland featuring six loops of about 5.179 miles. Relay teams of two to six can share the distance and an aid station is stocked with food and drinks.

A women only trail endurance event near Triangle VA offering 50K and 25K options, two roughly 15 mile loops, five aid stations, and a limited field with a 9 hour cut off.

Tackle forest trails on a two lap loop at Conway Robinson State Forest. This winter 10k offers series points, a technical shirt, and supports pet rescue. Walkers are welcome, and a virtual option is available.

Trail marathon and 50K on March 7, 2026 at Seneca Creek State Park near Gaithersburg, MD. Runners may stop at the marathon finish or continue to complete the 50K, and entries include a tech shirt and finisher medal.

A 3k and 5k cross country event at Creek’s Edge Winery on March 7 with chip timing, finisher medal, technical shirt and a post-race wine option. Walkers and a virtual race option are available, and points count toward multiple series standi..

A 5k and 10k at Smoketown Brewery on March 8 with out and back gravel courses, limited water stations, a virtual option, chip timing, a finisher medal, a technical shirt and a postrace beer.

A free International Women’s Day endurance day at Beaverdam Reservoir Park featuring a 7.5-mile loop and varied trail surfaces. The event centers women, offers course support through sunset, and focuses on movement and mutual support.