Trail Running calendar near Oakton 2026-2027

Event Overview The Catoctin 50k Trail Run takes place in June. It offers two distances: a 50k (approximately 32 miles) and a 25k called the "Half Cat." The event is held in Cunningham Falls State Park and Gambrill State Park near..

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in the heart of Georgetown. Choose between a 5k or 10k course located right near the nations capital.

A trail running event at Seneca Creek State Park on June 27, 2026, offering measured 5K and 10K courses through singletrack with lake views, aid stations, post-race food, and age division awards.

Experience a mud run featuring obstacles and trails in King George Virginia. With four mile and one mile options plus team challenges this event supports local community eye and hearing care services.

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 scenic out and back race on the mostly flat Dahlgren Railroad Heritage Trail. Choose between a half marathon or 50K distance and enjoy a well supported course featuring finishers medals and cash prizes.

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.

The MD Heat Trail Race on August 15, 2026, offers 50K and 25K trails with river crossings and valley views. Finish with a celebration featuring craft beer and BBQ.

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.