Trail Running calendar near Cockeysville 2026-2027

A six hour endurance run and a three person relay at Quiet Waters Park in Annapolis. Loops are about 4.25 miles with two aid stations on course, awards by category, and a branded sport duffel premium.

A running event at 868 Estate Vineyards in Purcellville, VA on July 25, 2026, offering in-person 5 km and 10 km courses plus virtual entry choices with tiered fees.

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 a half marathon along the Chesapeake & Ohio Canal in Georgetown on July 25, 2026, with in person and virtual options; walkers are welcome and each race has a specific start and finish location.

In-person 5K and 10K at Locust Shade Park in Triangle, VA on July 25, 2026, run on shaded scenic trails. Virtual entries are also available and walkers are welcome.

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.

Trail races at Little Bennett Regional Park on August 1, 2026 feature a 3.7 mile 5K plus and a 6.2 mile 10K on twisty singletrack with hills and streamside sections. Staging is near the Prescott Horse Trailer Area in Clarksburg Maryland.

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.

Looped trail ultras at Killen's Pond State Park near Felton, DE with 50 mile, 50 kilometer and 12 hour options on a roughly 3.1 mile mostly dirt loop. The format is self supported with water provided and manual lap timing.

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.

Trail running at Patapsco Pickall Area with 25K and 50K options on rolling single track, river crossings, mandatory out-and-backs, staffed aid stations with real food, and a postrace gathering with food and beer.

A muddy 5K with obstacles, slides and mud pits at DREAM Park in Philadelphia on August 15, 2026. The event includes an after-party with music, food and beer, day-before packet pickup, and a Buy One & Give One donation program.

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 5K and 10K held at Bull Run Marina in Clifton, VA on August 15, 2026, with in-person and virtual entry options and variable registration fees.

An evening three hour loop event at Roundtop Mountain Resort in Lewisberry, PA featuring a 1.5 mile loop with 600 feet of elevation gain and a separate kids race of about one mile. Pogs are awarded per lap and top finishers receive slammers..

A 7K trail race at the Woodstock Equestrian Center with a hilly course that circles fields and runs through wooded single track, presented as a 1969 throwback with 60s music and period attire encouraged.

GPS Too Hot to Trot is a four mile out and back race on the NCR Trail starting at the Paper Mill parking lot in Cockeysville, MD on August 19, presented as part of the 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..

Leopold’s Preserve 5k & 10k in Broad Run, VA on August 23, 2026 features 5 km and 10 km distances, welcomes walkers, and offers virtual entry options with medal and shirt choices.