Trail Running calendar near Pocomoke City 2025-2026

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

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 Run the Vineyards - Wind Vineyards 5K is a scenic race held at Wind Vineyards in Tappahannock, Virginia, featuring a 5K course on well-maintained trails of hard-packed dirt and grass across a 200-acre property. The mostly flat course includes two short hills and is chip-timed with awards for top..

The 22nd Annual Mariners Bethel Trail Run takes place at Camp Barnes in Frankford, Delaware, featuring 6.2-mile and 3.1-mile trail runs through the scenic Assawoman Wildlife Refuge. The flat, fast course follows cross-country roads and trails, beginning and ending at Camp Barnes. The event also offe..

The Talaria Trail Run takes place at Trap Pond State Park in Laurel, Delaware, featuring a scenic 4.5-mile race along the Bob Trail, a loop around the 90-acre Trap Pond. The course offers runners a vibrant autumn experience through towering hardwood forests, across a dam at Raccoon Pond, and over bo..

The Tuckahoe 25K is an annual trail running event held in Queen Anne, Maryland, featuring a 25-kilometer (15.5 miles) course primarily on single-track and horse trails. The terrain includes runnable hills, some rooty and muddy sections, but is not overly technical, making it suitable for both newcom..

The 27th Milford Cross Country Booster Reindeer Stampede 5k is a festive running event held at Killens Pond State Park in Felton, Delaware. This 5k run/walk features chip timing with MYLAPS BibTag and offers competitive walking and running categories. Participants receive long sleeve tee shirts and..

The Algonquin 50K is a challenging ultramarathon held in Pocomoke River State Park, Maryland, on the Delmarva Peninsula. The mostly flat, fast course covers approximately 31 miles on 95% trail, including single-track and horse paths, with sandy sections and possible standing water adding difficulty...

The Race4Warriors Half Marathon is part of a multi-distance event held in Lewes, Delaware, featuring 5K, 10K, and Half Marathon challenges. The race supports Wounded Warriors and Homeless Veterans and aims to unite military and civilian communities. The USATF-certified course starts and finishes at..