Trail Running calendar near Annapolis 2026-2027

A trail-based running event at Needwood Lake Circle in Maryland on July 11, 2026 offering 5 km, 10 km and virtual entries with medal and shirt options.

A 5K and 10K event at Nottoway Park in Vienna, VA on July 11, 2026, with multiple virtual options and tiered entry fees.

Fair Hill Firecracker XC & Endurance Race is a cross-country and endurance running event on July 11, 2026, held at 2900 Montchanin Rd in Wilmington, Delaware, listed as a MASS XC & Endurance Race.

A summer trail race at Gunpowder State Park that crosses county lines and includes water crossings, rolling hills and mixed terrain. Entry is free with donations accepted and the field 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.

A timed six-hour endurance event at Quiet Waters Park in Annapolis with solo and three-person relay formats. The course is about 4.25 miles per loop, with aid stations on the route and awards by overall and age-group distance.

A vineyard run on July 25, 2026 at 868 Estate Vineyards in Purcellville, Virginia offering 5 km and 10 km courses plus virtual entry options with varying fee tiers and medal or shirt choices.

Trail running at Button Farm in Germantown, MD over twisty single track with stream crossings, log ramps, and farm fields. Options include a 5K and an about 10K course with aid stations, post race food, and optional medals.

Christmas in July 5k & Half in Georgetown, Washington DC on July 25, 2026 features races along the Chesapeake and Ohio Canal path with 5K, half marathon and virtual options; walkers are welcome.

Locust Shade 5k and 10k on July 25, 2026 uses shaded scenic trails at Locust Shade Park in Triangle VA. Walkers are welcome and virtual entries are available with medal and shirt options.

A four-event summer trail series in Lancaster County that is not a race. Participants choose their distance on local trails and return to a Common tent for breakfast, hydration, and social time.

Trail races at Bohemia Manor Farm Winery featuring *5K* and *8K* courses through vineyards, riverfront and wooded trails, chip timing with live results, finisher wine glass and an on-site after party with music and food.

Run through the wooded singletrack trails and streams of Little Bennett Regional Park in Maryland. Enjoy a community atmosphere with professional timing, post race breakfast burritos, and distances for different experience levels.

Trail 5K, 10K and a half-mile kids run at Miller Plant Farm in York, PA, on mixed farm and wooded surfaces; overall and age-group prizes, produce samplers for 5K/10K entrants, and 100% of proceeds benefit the WellSpan York Cancer Patient He..

Trail races of 5K and 3K at Codorus State Park Marina organized by Delone Catholic High School's cross country team; early registration includes a T-shirt and goodie bag and proceeds support several local funds.

An 8K cross-country race at Anne Arundel Community College on August 2, 2026, part of the Annapolis Striders Championship and Maryland/DC RRCA Grand Prix Series, with pre-registration fees and race day registration available.

A half marathon and a 50K on the Dahlgren Railroad Heritage Trail in King George, VA on August 8, 2026. Mostly flat rails to trails courses with time limits, finisher medals, apparel options and postrace food including free MooThru ice crea..

Looped ultramarathons at Killen's Pond State Park near Felton, DE, with 50 mile, 50K, and 12-hour options on a shaded 3.1 mile dirt loop. The event is self-supported, manually timed, and limited to 30 entrants per race.

A wooded trail race at Gunpowder State Park on August 9 with mostly single track loops of about 4 miles. Participants can run one loop for 4 miles or two loops for 8 miles.

A trail race in Elkridge, MD on Aug 15, 2026 offering 25K and 50K options on rolling single track with river crossings. Aid stations provide water and real food and the finish area includes food, beer, and shelter.