Trail Running calendar near Leonardtown 2025-2026

The Pemberton 24 is a unique endurance running event held at Pemberton Park in Salisbury, Maryland. Participants, either solo or in four-person teams, run multiple 5K races over a 24-hour period, with a new 5K starting every hour. The scenic trail course features an aid station stocked with refreshm..

9K for Semper K9 is a community running and walking event in Fredericksburg, Virginia, held at Old Mill Park along Canal Path by the Rappahannock River. The program includes a 9K race and a Kids .9 Mile Fun Run, welcoming runners, walkers, families. The course runs along canal paths in downtown Fred..

St. Anselm's Family 5k is a family-friendly fundraising race in Washington, DC, held at 4501 South Dakota Ave NE. The event covers a 5k distance on a double-loop trail course, suitable for runners and walkers alike.It benefits a memorial scholarship fund at St. Anselm's Abbey School, supporting stud..

The Kellie Thompson Shiley 5k and Family Fun Run is an annual event held at the Terrapin Nature Trail in Stevensville, Maryland, on the scenic Eastern Shore. It features a 5K trail run/walk and a 1-mile fun run for children aged 10 and under. The race honors Kellie Thompson Shiley’s competitive spir..

The Brandy Station Battlefield 10k is a trail running event held at Brandy Station Battlefield in Virginia. The course combines cross country terrain with gravel dirt roads, featuring slight elevation gains but no major climbs. Runners can choose between 5k and 10k distances, with the 10k route bein..

Run the Vineyards - Wind Vineyards 5K is a scenic trail race held at Wind Vineyards, 5178 Richmond Highway, Tappahannock, Virginia. The 5K route runs on well-groomed, hard-packed dirt and grassy trails across the 200-acre property, with two short hills and mostly flat sections. The event features ch..

Run to the Taproom - Creekside Farm Brewery 5K & 8K takes place at Creekside Farm Brewery in King George, Virginia. The event offers scenic 5K and 8K courses on a well-maintained dirt trail through a 1,000-acre farm bordering the Rappahannock River. It is chip-timed with awards for Top 3 Overall and..

Hosted by the Association of the United States Army Southern Virginia Chapter, the Southern Virginia 5K offers a 5K Run/Walk and a 10K Run/Walk along the Capital Trail in Charles City, Virginia. The course runs on the scenic Capital Trail with options for all paces. The event takes place at 9220 Joh..

Quantico 24-Hour Walk, Run & Relay for Charity is held in Quantico, Virginia, benefiting Semper Fi & America's Fund, which supports wounded service members and military families. The event invites walkers, runners, and relay teams to cover mileage by doing laps or jogging several miles, with team an..

The Fall Harvest 5k is a scenic trail race held at Claude Moore Park in Sterling, Virginia. Set amidst the vibrant colors of autumn, the course features forest paths and leaf-covered trails, offering a picturesque experience for both runners and walkers. This event is part of the Run Your PRCS Parks..

Howlin' Coyote Canicross Trail Race, held in King George, Virginia (11617 Caledon Rd), offers two canicross options: a 10K Canicross and a 1-mile Wild Pup. This dog-friendly, non-profit event is part of the Friends of Caledon State Park series and supports natural resources and educational programmi..

The Pocahontas Trail Festival is a trail running event held at Pocahontas State Park in Chesterfield, Virginia. It features a Half Marathon and a 10k race, both starting and finishing on a large grass field near the park's boat launch. The course was redesigned to emphasize trail running, incorporat..

The Full Distance 10k is a scenic trail running event held at Locust Shade Park in Triangle, Virginia. The course features a mix of trails and pavement, with about 40% paved and some hills, consisting of four loops for the 10k distance. This chip-timed race welcomes both runners and walkers and is p..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. The course is a natural trail through the park, with water st..

Coastal Walk & 5K Run is a charity running and walking event held at Assateague State Park in Berlin, Maryland, located at 6915 Stephen Decatur Highway. Organised to support Coastal Hospice, it offers two options: a Coastal Hospice 5K Run and a Coastal Hospice 2 Mile Walk. The 5K course starts on a..

The Westover 5k & 10k is a flat, scenic race at Bluemont Park in Arlington, Virginia, along the W&OD Trail. The course is an out-and-back, with the 10k running out-and-back twice. The event is part of Bishop’s Events’ Year-Long 5k/10k/Back of the Pack Series and Fall Series.Walkers and strollers are..

The Wilderness Run 10k is a scenic cross-country trail race held at Wilderness Run Vineyard in Spotsylvania, Virginia, situated on historic Civil War battlefields. The course features rolling hills, with the 10k consisting of two laps of the 5k out-and-back route. Participants enjoy a vibrant atmosp..

The 22nd Annual Mariners Bethel 6.2m & 3.1m Trail Run takes place at Camp Barnes in Frankford, Delaware. The flat, fast course begins and ends at Camp Barnes, winding through cross-country roads and trails in the Assawoman Wildlife Refuge. In addition to the 6.2-mile and 3.1-mile trail runs, there a..

EX2 Adventures hosts the Fall Backyard Burn Trail Run at Lake Fairfax Park in Reston, Virginia. The event offers 5-mile and 10-mile trail options on a mostly singletrack course with a short prologue and minimal pavement, featuring views of Lake Fairfax, challenging rocks and roots, and a few short c..

North Point Fright Night 5K & Haunted Trail is a Halloween-themed community event at North Point High School in Waldorf, Maryland, on October 25, 2025. The day features a 5K on the school’s official cross-country course (certified for competition) with three race waves: Elite, Middle School & Younge..