Trail Running calendar near Annandale 2026-2027

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.

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.

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.

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 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..

Races at Third Winchester Battlefield in Winchester VA on August 8, 2026 include 5K, 10K, a half marathon and virtual options with medal or shirt. Walkers are welcome and registration shows tiered pricing.

Trail races on mostly single-track woods in Gunpowder Falls State Park, using a roughly 4 mile loop. Participants can run one loop for 4 miles or repeat it for 8 miles; registration is race morning only.

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.

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.

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.

A trail race at Bull Run Marina on August 15, 2026 offering 5K and 10K distances plus several virtual entry options. The route follows the Bull Run Occoquan Trail and registration uses tiered fees that include mandatory charges.

A 7K trail race at The Woodstock Equestrian Center in Dickerson, Maryland, presented as part of MCRRC's low key series for members. Non member registration has a $20 fee and runs from February 10, 2026 to August 16, 2026.

A four mile out and back run on the NCR Trail starting from the Paper Mill parking lot in Cockeysville. This weekday evening event is part of the Baltimore Road Runners Club Grand Prix Series.

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..

A community road event at Leopold's Preserve in Broad Run on August 23, 2026 offering 5 km and 10 km on-course races plus virtual options with medal and shirt choices. The race is part of the Sippin Series with Farm Brewery at Broad Run and..

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.

A self-timed 5 miles on a packed rail trail in Darlington, Maryland, held as part of the Harford County Running Club Dog Days of Summer Series. The course is stroller friendly with parking at Fisherman's Log and free registration.