Trail Running calendar near Annapolis 2026-2027

A 50 mile trail run in Clifton, Virginia on April 4, 2026, featuring forested, rolling terrain and spring bluebells. The 32nd running includes a 13 hour cutoff, a $125 entry fee, and Trail Sisters approved amenities.

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.

Experience a unique 14 mile point to point trail run through the forests of Virginia. Enjoy a flat course featuring themed aid stations serving pie and s'mores while supporting local children's charities.

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 a unique trail run on the private ThorpeWood estate in Maryland. Offering 5K and 10K distances, this club event features marked loops through beautiful natural terrain for FSRC members.

A turtle-themed 5K trail run at Hopkins Farm Brewery that supports local wildlife conservation. Participants receive a wooden medal and costume prizes are awarded. The event concludes with a festive after-party featuring live music.

Experience a scenic trail run at Pohick Bay Regional Park featuring waterfront views and historic surroundings. Choose between 5.9 and 10.4 mile courses through single track trails with professional support and activities for the whole fami..

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.

A memorial trail event at Piney Run Park featuring a 5.25 mile loop used for 50K, 25K, a 5 miler and an 8 hour challenge. Aid stations and loop transition support are provided and finishers receive a hat or visor and a medal.

Enjoy a cross country style 5k run or walk through the scenic Hauser Hill Event Center. Participants receive a finisher medal and a pour of wine in a collectible glass at the finish line.

A trail ultramarathon in Gunpowder State Park with 25K and 50K options on a 15.5 mile loop. Staffed aid stations and a nine hour time limit support runners throughout the course.

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.

Trail run at Lake Fairfax Park in Reston, VA featuring mostly smooth singletrack, lake views, and short technical sections. Choose 5.1 miles (one lap) or 10 miles (two laps) with options for swag, optional medals, and a supervised kids prog..

Experience a scenic 5K cross country race through the hop yards and vineyards of Red Shedman Brewery. Finishers enjoy a complimentary beverage at this unique farmhouse event in Mount Airy.

A *100-mile* ultramarathon on the C&O Canal towpath near the Potomac River, run as one ~40-mile loop plus two ~30-mile loops. Aid stations appear every 3–6.9 miles and the event is a WSER 2027 qualifier.

Experience a unique trail race through an active rock quarry at the Luck Stone Leesburg Plant. This 5K event supports environmental preservation and features family activities and awards for all ages.

An annual 5K at Marymount University on April 25, 2026, run on the Bluemont and Custis Trails with a post-race gathering, a virtual option, chip timing, and guaranteed shirts for early registrants.

Run a scenic 5k around the Bluemont Station Brewery property in Virginia. The event welcomes both runners and walkers and offers in-person and virtual participation options.

Run or walk a 5K trail race under the Flower Moon at Brandywine Creek State Park. This inaugural event supports local trail nonprofits and finishes with a moonrise celebration featuring s'mores and lawn games. Leashed dogs are welcome to jo..

Farm Park Challenge is a trail running event at the Agricultural History Farm Park in Derwood, Maryland on May 2, 2026. Options include a marathon, a 25K, and timed three hour six hour and ten hour challenges run as five mile laps.