Trail Running calendar near Wicomico Shores 2026-2027

Experience a scenic cross country trail run through Wilderness Run Vineyards featuring a 5K and 1 Mile distance. Enjoy post race live music and refreshments at the winery to support St. Patrick School.

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

Run loops on the scenic trails of Calvert Cliffs State Park. You have six hours to cover as much distance as you like, with aid and hot meals provided. A virtual option is available.

The Capital Backyard Ultra is a "last runner standing" race in Lorton, Virginia, capped at 60 runners. Competitors run a 4.167-mile loop every hour until only one remains. The winner receives a $1000 prize.

Event Details The Women's Trail Festival is a two-day event at Freedom Park in Williamsburg, VA, scheduled for a Saturday and Sunday in late March. The event features trail running and hiking options over two distances. Distances and Format..

Experience a scenic trail run through the forests and fields of Rosaryville State Park. Choose from several distances on fast and smooth terrain located just off the Capital Beltway in Maryland.

Experience a timed trail ultra at Little Bennett Regional Park with 5 and 9 hour individual or relay options. Runners navigate a 4.4 mile loop supported by a fully stocked aid station in Clarksburg.

Run along the paved B&A Trail in Maryland at this established event featuring a full and half marathon. Managed by the Annapolis Striders, it offers a well supported experience starting at Severna Park High School.

Run 7 miles of scenic trails at Cromwell Valley Park. Enjoy rolling hills, single-track paths, and a fast downhill finish. Proceeds support the park and therapeutic programs for veterans.

Experience a fast and flat trail run along the Rappahannock River in Fredericksburg. This 5k course features a smooth lollipop style loop with minimal elevation gain and scenic views starting from the local quarry.

Experience a 50 mile trail run along the scenic Occoquan River in Virginia during the peak of spring. This historic event features forested paths and the largest bluebell stands on the East Coast.

Run a scenic 5k cross-country course at a Virginia vineyard. The event welcomes runners and walkers alike and offers virtual participation options. It takes place in Warrenton on April 4, 2026.

Run a memorable 14-mile point-to-point trail adventure from one Sheetz to another. This untimed event features themed aid stations with unique snacks, supports local charities, and provides useful swag like an insulated travel mug.

This backyard ultra adds a brutal twist: runners must complete a 4.167-mile loop every hour while carrying an extra pound each lap. The race goes on until only one person remains. It's a test of endurance where the load increases but the ti..

Experience a hilly and technical trail race through the scenic property in Bluemont Virginia. Choose between the 5k and 10k distances and enjoy a glass of beer after conquering the technical terrain.

Experience scenic trail running at Pohick Bay Regional Park with 5.9 and 10.4 mile courses. Enjoy waterfront views and technical single track trails followed by a community atmosphere and post race breakfast burritos.

Experience a fast and flat race along the scenic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners are invited to set new personal records at Carderock Park.

Run to Remember is a multi-distance trail event held in Sykesville's Piney Run Park. Runners traverse a scenic 5.25-mile loop past woods, meadows, and a lake. The event honors lost loved ones and supports cancer research.

Join the Sip & Stride 5k and 10k in Louisa Virginia for a chance to earn points in the Sippin’ Series. Choose between in person racing or multiple virtual participation options with medals and shirts.

Experience the scenic grounds of Barrel Oak Winery in Delaplane, Virginia, through 3k and 6k race options. This inclusive event welcomes both walkers and leashed pets for a day of activity in a beautiful vineyard setting.