Trail Running calendar near Hillsboro 2026-2027

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.

A just under 50 km trail run in the southern Massanutten range with about 5,700 ft of elevation change, six aid stations, and a start and finish at the Route 211 parking area. Entry is limited to 75 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.

Trail races at Miller Plant Farm featuring 5K, 10K, and a kids 0.5 mile run across mixed farm and wooded terrain, with on-site medical support and fundraising proceeds benefiting the WellSpan York Cancer Patient Help Fund.

A community 5K and 3K trail run at Codorus State Park Marina on August 1, 2026, with all profits distributed to four named funds. Pre-registration details and awards are specified, and a T-shirt is included for preregistrants.

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.

A race day at Third Winchester Battlefield on August 8, 2026 offering 5K, 10K, and half marathon distances plus virtual options and tiered registration fees; walkers are welcome and courses pass through battlefield scenery.

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.

All trail race at Patapsco Pickall Area offering 25K and 50K on rolling single track with technical sections and river crossings. Aid stations provide water Tailwind and real food and the finish includes shelter food and beer.

A trail 5K in Gettysburg on August 15, 2026, with a race shirt option for early registrants and an event bottle opener medal. Brewfest options and tours of the Daniel Lady Farm House and Barn are available the same day.

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.

A memorial 5K trail run at Genesee Valley Outdoor Learning Center in Parkton, MD, with a 5K, 1-mile walk, kids dash, team entries, and an In Spirit donation option. Proceeds support a scholarship fund and a post-race festival offers food an..

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.