Trail Running calendar near Prince Frederick 2026-2027

Community trail event at Camp Barnes in Frankford, Delaware offering 6.2 and 3.1 mile runs, 1 to 3 mile family walks, and a Kiddie Color Run. Post race lunch and live bluegrass music support Mariners Bethel youth ministries.

A donation supported 5.25 miles trail race at Gunpowder State Park with a steep opening climb, single track sections, and on site race day registration.

Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

Trail 5 km and 10 km races plus several virtual entry options at Conway Robinson State Forest on October 25, 2026; walkers are welcome.

Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.

5th Annual Mackyard Ultra is a race by the Baltimore Road Runners Club on October 31 at Shawan Downs in Cockeysville, MD with a $20 entry fee and a 100 runner limit.

Scenic 5 km and 10 km races through Burke Lake Park on October 31, 2026, with in-person and virtual entry options; walkers and strollers are welcome.

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Trail 5 km and 10 km races at Burke Lake Park on November 7, 2026, with walkers welcome and virtual entries offering medal and shirt options.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.

Trail and virtual runs at Valor Ranch in King George VA featuring timed 10K and 5K events, a 10K ruck, a 1 mile fun run, and 100 percent of proceeds supporting Valor Ranch charitable programs.

A fall trail event at Trap Pond State Park featuring a 4.5 mile loop on the Bob Trail and a 2 mile walk. Participant fees support Legacy Academy.

Looped 50K and 20K trail races at Rosaryville State Park near Upper Marlboro MD, single track woods, two aid stations, drop bag support and military awards.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre Thanksgiving run at Barrel Oak Winery in Delaplane offering 3K and 6K courses, virtual entry options, and walk and leashed pet access.

A free 5K cross country at Herring Run Park on November 15 featuring mixed surfaces, two river crossings, wooded trails, and donations accepted for local scholarships and park support.

A 25K trail race in Queen Anne, MD on November 21, 2026 featuring single-track and horse trails, three aid stations, and awards for top finishers.

A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are re..