Trail Running calendar near Annandale 2026-2027

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..

A running event at Third Winchester Battlefield on August 8, 2026 offering 5K, 10K and a Half Marathon. Virtual entries are available and walkers are welcome.

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 the Patapsco Pickall Area near Elkridge, MD offering 25K and 50K courses with single-track, river crossings and 2000+ ft of climbing, staffed aid stations, and a post-race food and beer spread.

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.

In-person 5K and 10K races run along the Bull Run Occoquan Trail at Bull Run Marina in Clifton, VA on August 15, 2026; virtual entries are available with different medal and shirt options and fees vary by registration period.

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..

In-person 5K and 10K races at Leopold’s Preserve in Broad Run on August 23, 2026, with virtual entry options and registration tiers. The event is part of the Sippin Series in conjunction with the Farm Brewery at Broad Run; walkers welcome.

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.

A trail event at Dirt Farm Brewing in Bluemont offering 5K and 10K courses over rugged, hilly terrain on August 29, 2026. Virtual entries are available with medal and shirt options.

A family-friendly 5K mud run on August 29, 2026 at Budds Creek Motocross Park featuring obstacles, mud pits, a pre event warm up, and an after party with music and food. Value and VIP registration options are available.

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.