Trail Running calendar near Annapolis 2026-2027

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 six-hour endurance run and three-person relay at Quiet Waters Park in Annapolis on July 19, 2026. The course is a roughly 4.25 mile shaded loop with aid stations, age-group and overall awards, and participant premiums.

A 5K and 10K run around the grounds of 868 Estate Vineyards in Purcellville, Virginia on July 25, 2026. Virtual entries and tiered registration options are offered, including choices for medals and shirts.

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.

A 5K and half marathon run along the Chesapeake & Ohio Canal path in Georgetown Washington DC on July 25, 2026. Walkers are welcome and virtual entries are available with medal and shirt options.

A July trail event at Locust Shade Park in Triangle, VA offering 5K and 10K distances plus multiple virtual options. The courses run on shaded, scenic trails and walkers are welcome.

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.

A community 5K trail run at Rock Creek Picnic Shelter in Derwood, MD, on July 26, 2026. Part of the PAMOJA Weekend, the event highlights unity, culture, wellness and community connection.

Trail races at Bohemia Manor Farm in Chesapeake City feature 5K and 8K courses through vineyards, wooded trails and along the river, with chip timing, age group awards, finisher wine for ages 21 plus and an on-site after party with music an..

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 relaxed practice run on August 2, 2026 at Fountainhead Regional Park with route options from 6 to 13+ miles. Entry is open but limited to 60 and requires sign up; light refreshments are provided.

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 trail ultramarathons at Killen's Pond State Park near Felton, DE, with 50 mile, 50K and 12 hour options. Events are self supported, manually timed, capped at small fields, and run in summer conditions.

Part of the Harford County Running Club Dog Days of Summer Series, Rigbie Farm 5k is a free, self timed grass and trail loop near Darlington, MD. Parking is at Rigbie Farm and non members may take part in three free runs.

The Bunker Hill Trail Races will take place in Parkton on Sunday 9 August 2026. You can run between 4 and 8 miles.

Trail event in Elkridge, MD with 25K and 50K options on rolling single track featuring technical sections, river crossings, multiple aid stations with real food, and a post-race pavilion gathering.

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.