Trail Running calendar near Annapolis 2025-2026

The Fall Backyard Burn Trail Run at Hemlock Overlook in Clifton, VA, is a scenic trail running event featuring 5-mile and 10-mile race options. Set in a 425-acre park along the historic Bull Run, the course offers a mix of hiking trails, old dirt roads, stream crossings, grassy fields, and minimal p..

The Tuckahoe 25k is a trail race in Queen Anne, Maryland. It covers 25k (about 15.5 miles) on mostly single-track trails with some wider horse trails. The course is not overly technical but includes runnable hills, rooty, muddy sections, and varied conditions.Runners can expect three fully stocked a..

Hex Hollow Half takes place at Spring Valley Park in southern York County, Pennsylvania. Runners choose between a 13.13-mile half marathon (two loops) and a 6.66-mile single loop. The course traverses low meadows, mature hardwood forests, and pine-covered wide tracks, featuring roots, rocks, two str..

The Fall Backyard Burn at Laurel Hill is a trail running event held at the Workhouse Arts Center in Lorton, VA, set within 1600 acres of scenic former prison grounds. The course features a mix of forested and open meadow singletrack trails, primarily dirt and crushed stone, with minimal pavement and..

The Winery at Bull Run Turkey Trot offers a scenic trail 5k and 10k through the Manassas National Battlefield Park, starting and finishing near The Winery at Bull Run in Centreville, VA. The course is a cross-country style route across battlefield trails, including dirt paths, a boardwalk, and grave..

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..

Now in its 27th year, the Milford Cross Country Booster Reindeer Stampede 5k takes place at Killens Pond State Park in Felton, Delaware. The event offers a 5k run/walk and a competitive walking option, benefiting Milford High School Cross Country. The course, mapped in advance, emphasizes a family-f..

The Run for Valor 10K is a trail running event held at Valor Ranch in King George, Virginia. The race features a 10K run, a 10K weighted ruck, a 5K run, and a 1-mile fun run/walk suitable for all ages and paces. The course traverses farm trails, pastures, woods, and gravel roads, with uneven terrain..

Devil Dog Ultras is a trail ultramarathon in Prince William Forest Park, VA. It offers 100-mile, 100K, and 50K loops on trails with roots and rocks, plus fire roads. The first loop is 23 miles; subsequent loops are 19.5 miles.The 50K is one loop plus a 9-mile extension; the 100M runs five loops and..

The Fall Backyard Burn Trail Run at Fountainhead Regional Park in Fairfax Station, VA, is a popular trail running event held annually, with the 2025 race scheduled for December 7. The course features scenic hiking trails and old dirt roads along the Occoquan Reservoir, offering two distance options:..

Angela Ivory Memorial Runs take place at Killen’s Pond State Park in Felton, Delaware, offering three distances: 50K, 100-mile, and a 24-hour race. The course is a 3.1-mile dirt loop contained within the park, featuring mostly flat terrain with a few roots and rocks and a short footbridge. Races are..

Located at Rockburn Branch Park in Elkridge, Maryland, the Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon built from six loops of about 5.18 miles through wooded trail terrain. The event also offers a 50k relay, allowing teams of up to six runners to share the distance with exchanges aft..

The Dahlgren Trail Half Marathon, held in King George, Virginia, offers a scenic out-and-back course along the flat, smooth Dahlgren Railroad Heritage Trail. This event features a 13.1-mile race on an old railroad bed, providing a comfortable and picturesque running experience. Participants enjoy ca..

Froggy Hollow 5 & 9 presented by Altra is a Charm City Run signature trail ultra held at Little Bennett Campground in Clarksburg, Maryland, inside Little Bennett Regional Park. The event includes 5-Hour Challenge, 5-Hour Relay, 9-Hour Challenge, 9-Hour Relay, and More Than a 4-Miler, all based on a..

Paradise Springs 5k & 10k is a trail race at Paradise Springs Winery in Clifton, VA, offering a technical Hemlock Overlook Park course by the river. The 10k is two laps of the 5k route, with substantial elevation changes and a rocky section. Runners receive a finisher medal, technical shirt, a glass..

The Winter Conway Robinson 10k is a trail running event held at Conway Robinson State Forest Park in Gainesville, Virginia. The race features a scenic loop course through forest trails with some technical terrain and minor hills, with the 10k consisting of two laps of the 5k route. Walkers are welco..

No Man's 50K is a women-only trail running endurance event held in Triangle, Virginia, featuring 25K and 50K distances. The course consists of two loops of approximately 15 miles each, designed as a great first-time ultramarathon route. Runners experience a mix of terrain with about 70% single track..

The Dark Side 8 Hour Ultra is an eight-hour trail race at Little Bennett Park in Montgomery County, Maryland, near Clarksburg. The course is a 5.5-mile loop run mostly on single-track trails, starting at the Little Bennett Campground Pavilion. Runners may complete as many laps as they wish within th..

Blazing Saddles is a trail running event hosted by the York Road Runners Club at Codorus State Park in Hanover, Pennsylvania. Scheduled for March 14, 2026, it offers two race distances: a 25K and an 8 Miler. Both courses run along the scenic Ranger Trail, featuring a mix of horse trails, single-trac..

HAT Run 50k takes place in Havre de Grace, Maryland, offering a challenging 50-kilometer trail race. The course blends mostly single-track trail with open fields, dirt roads, and a stretch of paved road, featuring nearly 4,400 feet of total climbing. Runners start with a 3-mile loop, then complete t..