Trail Running calendar near Winchester 2026-2027

Run the scenic Puso 10K on the flat, gravel C&O Canal path in Georgetown, Washington DC. This chip-timed event benefits the PUSO Foundation and awards top finishers. All participants receive a finisher's medal and tech shirt.

The Canaan Valley Trail Run takes place on the scenic Promised Land Trail loop in West Virginia's state park. Choose a 5.9-mile or 11.8-mile distance and receive a medal, shirt, and post-race refreshments. Experience the natural beauty of T..

Kick off the Blue Crab Bolt trail series with this scenic run at Seneca Creek State Park. Choose between a 5K or 10K course on park trails featuring lake views and streams. The event also offers a chance to support a local nonprofit charity..

This cross-country event takes place at the Agricultural History Farm Park in Derwood, Maryland. It's part of a free series for members, with paid registration available for non-members and a youth discount.

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

A cross country 5k and 10k at 868 Estate Vineyards with chip timing, a virtual option, race awards, and a postrace glass of wine for participants.

Tackle the flowy and fun trails at Schaeffer Farms in Germantown, Maryland. Choose from a 5K or a 10K++ course featuring single-track, stream crossings, and open fields. Enjoy post-race food, optional medals, and a festive atmosphere.

Run a festive half marathon or 5K on the scenic C&O Canal path in Georgetown. The event benefits the Purple Heart Foundation and counts towards year-long running series points. Participants receive a medal, tech shirt, and chip timing.

Explore the wooded trails of Little Bennett Regional Park in this trail run. Choose between a beginner-friendly 5K+ or a 10K course featuring single-track paths, hills, and streams. The event includes race swag, post-race food, and a free k..

Run a 5k, 10k, or half marathon on the scenic trail loops of the Third Winchester Battlefield. The event includes chip timing, a finisher's medal, and supports Operation Enduring Warrior. Walkers are welcome, and participation counts toward..

A trail race in Elkridge, MD on August 15, 2026 offering 25K and 50K options on rolling single track with river crossings, aid stations with real food, and an on-site finish area with pavilions and refreshments.

Run on the flat, scenic dirt trails of Leopold's Preserve in this 5k and 10k event. Participants receive a medal, shirt, and chip timing, with points counting towards several annual series. A virtual race option is also available.

The Inferno 10k is a forest trail race on a looping course behind Dirt Farm Brewing in Bluemont. Runners tackle a route with roots, rocks, and elevation changes. Finishers earn a medal, a tech shirt, and a post race beer.

Trails 4 Tails at Codorus State Park features a 40 mile ultra, a 40 mile team relay, and a 25K on looped trails with varied terrain, on-course aid, nearby camping, and awards for top finishers.

Test your endurance on a scenic 10-mile loop at Seven Bends State Park. Choose from distances like the 10-miler, 50k, 50-mile, 100-mile, or a Last Man Standing Ruck challenge. This event features mixed terrain, strict cutoffs, and is organi..

Event Information The River's Edge Endurance Challenge takes place in Brunswick, Maryland. The event is the 8th annual edition and offers three different race distances. Distances 5K (3.1 miles) 3 Hour Endurance Race 6 Hour Endurance Chall..

The Trails 4 Miles will take place in Stephens City on Saturday 26 September 2026.

This community 5K run/walk takes place on a wide natural trail at the Agricultural History Farm Park. The event includes a pre-race pep rally, post-race snacks, and awards for top finishers.

This annual trail event in Mount Airy, Maryland, offers three distinct challenges: a 5-mile trail run, a 4-hour challenge, and an 8-hour ultra. Organized by the Frederick Steeplechasers, it honors the memory of beloved club members. Proceed..

The Rocky Gap Trail Run features a 25K and 50K course through the scenic loops of Rocky Gap State Park. Runners can participate solo or in relay teams of 2 or 3. The event includes a base camp aid station and on-course support.