Trail Running calendar near Frederick 2026-2027

This cross-country event takes place at the Agricultural History Farm Park in Derwood, Maryland. It's part of a free series for members, with paid registration available for non-members and a youth discount.

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

A summer trail race at Gunpowder State Park in Sweet Air, Maryland, listed as 7 miles but described as roughly 8 miles with county crossings, rolling hills, water crossings and occasional mud. Capacity is limited to 100 runners.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

Experience a scenic run through the 868 Estate Vineyards in Purcellville. Choose between 5k and 10k distances or participate virtually for an afternoon of outdoor activity at a Virginia vineyard.

Experience the twisty single track and scenic farm fields of Germantown at this trail running event. Participants can choose between two distances while supporting local non profits in Montgomery County.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in Georgetown for the Christmas in July 5k and Half. Participants can choose between two race distances or join virtually from any location.

Trail races at Little Bennett Regional Park on August 1, 2026 feature a 3.7 mile 5K plus and a 6.2 mile 10K on twisty singletrack with hills and streamside sections. Staging is near the Prescott Horse Trailer Area in Clarksburg Maryland.

Experience a rugged all terrain race through a working Century Farm in Southern York County. Run across grassy trails and muddy creeks to support cancer patient care while enjoying scenic farm views.

Experience the scenic and historical landscape of Winchester Virginia with a 5k, 10k, or Half Marathon at Third Winchester Battlefield. Both runners and walkers are welcome to participate in person or virtually.

Join this annual memorial event in Schellsburg for a 5K run or walk through scenic rolling hills or a family friendly flat course. Support local scholarships while competing for age group awards and cash prizes.

Trail race in Elkridge, Maryland offering 25K and 50K on rolling single track with river crossings, technical sections and multiple aid stations serving real food, water and Tailwind.

Experience the MCRRC Groovin Woodstock 7K XC at the Woodstock Equestrian Center in Maryland. This low key cross country race offers a scenic 7 km route for club members and non members alike.

Experience the Leopold’s Preserve 5k and 10k in Broad Run Virginia. This Sippin Series event welcomes both runners and walkers for a scenic race through the preserve in collaboration with the Farm Brewery at Broad Run.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

Conquer rugged terrain and steep inclines at Dirt Farm Brewing in Bluemont. Choose between 5k and 10k distances through breathtaking landscapes and enjoy a post race beer at the finish line.

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

Experience a cross country race through Nottoway Park followed by a community picnic. This event features a three mile course and a kids fun run to celebrate the end of the summer season.

Test your limits in Kennedyville with the Savage Race or Savage Blitz. Navigate miles of mud and over 25 obstacles to earn exclusive medals and state pins at this premier Maryland event.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.