Trail Running calendar near Frederick 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 vineyard run at 868 Estate Vineyards in Purcellville, VA on July 25, 2026 offering 5k and 10k routes plus virtual entry options and tiered registration 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 July 25, 2026 running event in Georgetown, Washington, DC offering a 5K and a half marathon on the Chesapeake and Ohio Canal path, with in-person and virtual options; walkers are welcome.

Locust Shade 5k & 10k on July 25, 2026 at Locust Shade Park in Triangle VA offers shaded, scenic trail courses plus virtual options with medals and shirts. Walkers are welcome.

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.

Scenic road and trail races at Third Winchester Battlefield in Winchester VA on August 8, 2026, offering 5K, 10K and a half marathon plus virtual entry options with medal or shirt. Walkers are welcome and registration runs in phased windows..

A 5K run plus two 5K walks on August 9 2026 at Camp Living Water in Schellsburg PA, raising funds for annual scholarships for Bedford High School students and for families facing financial need after the loss of a young person.

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 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 running event on August 15, 2026 at Bull Run Marina in Clifton VA, offering in-person 5K and 10K races plus multiple virtual entry options with varying merchandise choices and tiered 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.

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 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, offering in-person and virtual options and included in the Sippin Series with the Farm Brewery at Broad Run.

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.

Trail-style 5K and 10K at Dirt Farm Brewing in Bluemont, VA on August 29, 2026, featuring rugged terrain, steep climbs, and virtual entry options with medals and shirts.

Muddy Dash Mechanicsville is a 5K mud run at Budds Creek Motocross Park with obstacles, mud pits and slides plus a festival style after party with music, food and beer. Registration options include standard and VIP packages.