Trail Running calendar near Leonardtown 2026-2027

Experience a dog friendly trail race through the varied terrain of Caledon State Park. Run a 10K or 1 mile course with your leashed companion to support local natural resources and educational programming.

Experience the scenic beauty of Pocahontas State Park at this trail festival featuring a loop course 10k and half marathon. Enjoy runnable trails and professional timing in a picturesque Virginia forest setting.

Trail runs at Laurel Hill in Lorton, VA on October 4, 2026, with singletrack through forest and meadows. Choose 5.4 miles or 10 miles; event features aid stations, post-race food, a kids program, and optional medals.

A trail event at Bretton Woods Recreation Center on October 11, 2026 featuring a 5K run and 1 mile walk to raise funds for addiction prevention, education and support; registration opens March 24, fee $30.

A trail run at Lake Fairfax Park in Reston, VA offering **5.1 mile** and **10 mile** singletrack courses with lake views, short technical sections, on-site bathrooms, a kids program, race swag, and optional finish medals.

Experience a scenic trail run through the Assawoman Wildlife Refuge at the 23rd annual Mariners Bethel event featuring various distances and a post race bluegrass celebration.

A scenic, well-marked trail event in Patapsco Valley State Park offering in-person and virtual 50k and 25k options, Brooks shirts, five aid stations, and distinct finishers awards for each distance.

A 24 hour endurance race at Greensprings in Williamsburg on October 24, 2026. Runners complete certified 2.215 mile loops on a mainly flat crushed gravel trail while supporting The Arc in Williamsburg.

Runnable, rolling trail loops in Prince William Forest Park offer **50 km** (two 16-mile loops) and **25 km** (one 16-mile loop) options on shaded trails with creek crossings. Entry is limited to 110 runners and there is no formal entry fee..

Experience a seasonal trail run or walk through the scenic Conway Robinson State Forest in Gainesville with 5k and 10k distance options for all participants.

Experience a scenic 5K cross country run through the historic Rocklands Farm Winery followed by an after party with live music and wine.

Trail races at Button Farm in Germantown, MD on November 7, 2026 feature twisty singletrack and open farm fields, with distances of 13.5, 6.7 and 3.2 miles. The event includes aid stations, portajons, finisher medals and post-race food.

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.

The Talaria Trail Run is a fall event at Trap Pond State Park in Delaware. It features a 4.5-mile race on the scenic Bob Trail and a 2-mile walk. Participation supports Legacy Academy.

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.

The Tuckahoe 25k in Queen Anne, MD on November 21, 2026 is a 25 kilometer trail race featuring mostly single track, runnable hills, and some muddy sections. Three stocked aid stations support runners and awards go to the top three men and w..

A trail race at Riverbend Regional Park on November 22, 2026 offering 5 mile and 10 mile routes on riverside singletrack with aid stations, post-race food, parking, and a kids program.

A 5K and 10K held at Carderock Park along the Chesapeake and Ohio Canal Towpath on November 22, 2026, with a flat, fast trail, walkers welcome, and virtual entry options that include medals and shirts.

Run a scenic Turkey Trot through the historic trails of Manassas National Battlefield. Choose between a 5k or 10k trail course and finish with a glass of wine from the Winery at Bull Run. Your participation supports the preservation of the..

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.