Trail Running calendar near Annapolis 2026-2027

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.

Run a technical 8K trail through vineyards and along the river at Bohemia Manor Farm. The chip timed event includes a tech shirt and wine glass. Celebrate after with a waterfront party featuring live music and food.

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.

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.

An informal, self-supported ultramarathon at Killen's Pond State Park with 50-mile, 50K, and 12-hour options on a shaded 3.1-mile dirt loop, manual lap counting, water provided, and strict storm safety rules.

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.

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.

The Tom LaMonica Memorial Trail Run will take place in Parkton on Saturday 22 August 2026. You can run 5 kilometers.

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.

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.

Experience the 15th annual Sasquatch Preservation Trail Run in Seven Valleys. Choose between the 5K or 10K courses and explore the natural landscapes preserved by the Farm and Natural Lands Trust.