Trail Running calendar near Annapolis 2026-2027

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.

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..

A community trail series meeting one Saturday each month through the summer, with three mornings and a sunset closing. Participants pick their own distance and return to a shared tent for breakfast, drinks, and company.

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 trail-style 5K and 10K at Dirt Farm Brewing in Bluemont on August 29, 2026, with rugged terrain, steep sections, and winding paths; virtual entries available with different medal and shirt options.

The Muddy Dash - Maryland will take place in Wicomico Shores on Saturday 29 August 2026.

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.

Opening Night 2026 at Morven Park in Leesburg, VA opens the cross country season with races for middle and high school divisions, a spectator friendly course, music and food. Course updates and awards info will be announced in May 2026.

A four-part community trail series with three morning gatherings and a final sunset event in Marietta and Lancaster County. Participants choose their own distance, share food and hydration, and may register per event or buy a multi event pa..

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

A half marathon and a 10K at Lums Pond State Park on 09/06/2026 using Little Jersey and Swamp Forest trails. Routes include single track and wider trails and have a relatively flat elevation profile.

Experience the 15th annual Sasquatch Preservation Trail Run in Seven Valleys. Choose between the 5K or 10K courses and explore the natural landscapes preserved by the Farm and Natural Lands Trust.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

A 24-hour event at Pemberton Park where individuals and four-person teams run repeated 5K loops, earning points per finish and for placing, with bonus points for late-night miles and a big bonus for completing all 24.

Trail races at Codorus State Park near Hanover PA offering a 40 mile ultra, a team relay and a 25K. The looped course mixes singletrack, fields and lakeshore and includes a stocked aid station.