Trail Running calendar near Winchester 2026-2027

Trail-based 5K and 10K at Rock Creek Regional Park in Derwood, MD, with virtual entry options and listed registration fees. The event also collects donated race medals for Medals4Mettle.

A 5K and 10K held at Nottoway Park in Vienna on July 11, 2026, with in-person and virtual entry options; published registration fees vary by entry date and include mandatory charges.

A roughly 50 km trail run on the Massanutten range with 5,700 feet of climb, six aid stations (two water only), varied terrain and scenic overlooks, finishing with a post-run gathering at the Route 211 commuter lot.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

A 5K and 10K run around the grounds of 868 Estate Vineyards in Purcellville, Virginia on July 25, 2026. Virtual entries and tiered registration options are offered, including choices for medals and shirts.

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 half marathon run along the Chesapeake & Ohio Canal path in Georgetown Washington DC on July 25, 2026. Walkers are welcome and virtual entries are available with medal and shirt options.

Trail races on the Lost Turkey Trail near Blue Knob State Park in Pennsylvania offer a 50K point to point, a 13.1 mile loop and a 10K(ish) option on single track and double track terrain.

A July trail event at Locust Shade Park in Triangle, VA offering 5K and 10K distances plus multiple virtual options. The courses run on shaded, scenic trails and walkers are welcome.

A community 5K trail run at Rock Creek Picnic Shelter in Derwood, MD, on July 26, 2026. Part of the PAMOJA Weekend, the event highlights unity, culture, wellness and community connection.

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.

A road and virtual event on August 8, 2026 at 251 First Woods Drive in Winchester, VA offering 5K, 10K, and half marathon distances with virtual options. Walkers are welcome and registration fees increase closer to the event.

Participate in a 5K run or walk at the Somerset Historical Center to support the North Star Cross Country team. Enjoy a dedicated cross country course with awards for various age groups and included event t-shirts.

A memorial trail run in the Jefferson National Forest featuring a roughly 60 km course and a 50 km Party Route option, three aid stations, limited entry, and a largely unmarked route supported by a GPX file and turnsheet.

A 6K cross country race beginning and ending at Death Ridge Brewery, using parts of the Verdun Adventure Bound course. The event features varied trails, ponds and bridged streams, race shirts for early registrants, and awards with proceeds..

An annual event on August 9, 2026 in Schellsburg offering a 5K run and two 5K walks. The race raises funds for memorial scholarships and features age group awards, race shirts for preregistered entrants and professional timing.

A trail race in Elkridge, MD on August 15, 2026 offering 25K and 50K on rolling single track with river crossings, aid stations, and a post-race gathering with beer and food.

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.