Trail Running calendar near Dickerson 2026-2027

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.

Pre-Thanksgiving 3K and 6K runs at Barrel Oak Winery in Delaplane with in-person and virtual options; walkers and leashed pets are welcome.

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 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..

Experience riverside singletrack at Riverbend Park with 5 and 10 mile trail races. This event offers scenic Potomac River views, a dedicated kids program, and professional race support in a beautiful natural setting.

Maryland Turkey Trot on November 22, 2026 at Carderock Park in Potomac MD offers 5k and 10k courses with virtual entry options; walkers are welcome.

A 5 km and 10 km trail race at The Winery at Bull Run in Centreville, VA, routed through the Manassas National Battlefield with virtual entry options.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

Thanksgiving morning 5K and 10K at Burke Lake Park with virtual options, medals, and a long sleeved technical shirt available.

Thanksgiving Day events at Sherando Park on 11/26/2026 include a 3.1 mile 5K plus a 100 m Tot Trot and two kids fun runs, each with specified registration windows and fees.

A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.

A trail-based 5K and 10K in Wheaton Regional Park on November 26, 2026, with in-person and virtual categories and points toward year-long series.

A Thanksgiving morning 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural trails; open to all ages, $15 registration fee.

Black Friday 5k and 10k at Frying Pan Park in Herndon on November 27, 2026, offering in person and virtual options plus onsite farm animals.

Trail and road races at Lake Anna State Park on November 27, 2026, offering 5K, 10K and half marathon distances plus virtual options.

A scenic Thanksgiving weekend 5K and 10K at Henway Hard Cider in Bluemont, VA on November 28, 2026, featuring post-race cider and virtual participation options.

Holiday-themed trail races at Burke Lake Park with 5K, 10K and half marathon distances plus virtual entries with medal and shirt options.

Trail loop ultras in Triangle VA offering 100 mile, 100K and 50K courses on mostly single-track terrain with stocked aid stations and set cutoffs.

Experience the beauty of Fountainhead Regional Park on a course featuring hiking trails and dirt roads. With two distance options and a dedicated program for kids, this event offers a complete day of trail running near the Occoquan Reservoi..