Trail Running calendar near Winchester 2025-2026

Hone Quarry Ultra - Dayton, VA The Hone Quarry Ultra is a trail endurance race that begins and ends at Briery Branch in the Shenandoah Valley and enters the George Washington National Forest near the Hone Quarry Recreational Area. The cours..

The Molon Lave 5k is a scenic cross-country running event held at Molon Lave Winery in Warrenton, Virginia. The course features three loops around the winery property, offering a fairly flat terrain with natural vineyard surroundings. Walke..

The Trail Demon 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features a technical forest trail loop with tree roots, rocks, and elevation changes, offering scenic views and a demanding..

Run a 50 mile trail race at Hemlock Overlook Regional Park, following the Occoquan River and Bull Run through rolling forest and long bluebell stands. The event blends local Civil War history with a Trail Sisters approved, inclusive vibe an..

The Breeze Thru The Trees 5k is a cross-country running event held at Ruppert Nurseries, a 500-acre tree farm located in Gaithersburg, Maryland, within Montgomery County’s Agricultural Reserve. The event features a 5K run and a 1-mile fun r..

Run to Remember at Piney Run Park features scenic 5.25 mile loops through woods, meadows and lakeside views, with distances from a 5 Miler to a 50K. Take on the 8 Hour Challenge, earn finisher swag, and support youth programs and cancer res..

Barrel Oak 3k & 6k is a cross-country running event at Barrel Oak Winery in Delaplane, Virginia. The course winds through vineyard grounds with gravel sections and rolling hills, and the 6k is two laps of the 3k route. Walkers and leashed p..

Run 100 miles along the scenic C&O Canal towpath near Knoxville Maryland on April 25 2026, a WSER 2026 qualifier. Smooth, low elevation loops along the Potomac with volunteer staffed aid stations.

Event information The event is a 5k held on April 26, 2026 at Bluemont Station Brewery & Winery in Bluemont, VA (18301 Whitehall Estate Ln). Points from the race count toward the Year-Long 5k & Back of the Pack Series and the Sippin..

Run scenic trails at Agricultural History Farm Park for the Farm Park Challenge. Choose marathon, 25K or 3 hour, 6 hour or 10 hour lap challenges where each lap must be under an hour. Volunteers get the same swag as finishers.

MMT 100 is a rugged, rocky ultramarathon on the Massanutten Mountains in Virginia’s George Washington National Forest, Shenandoah Valley. The 100-mile course includes short but steep climbs and more than 18,500 feet of total ascent, demandi..

Take on the More Miles Last One Standing Challenge on May 30 in Knoxville MD, a backyard ultra where runners cover a 4.167 mile loop each hour until one remains. Prize money, a 1 mile race, and a Backyard Ultra qualifier add the drama.

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This..

Run under the stars in Prince William Forest Park on a rugged 25 mile loop once for 25 miles or twice for the 50 mile night challenge. Singletrack trails, stocked aid stations, and limited crew and pacer support.

Highlands Sky 40M is West Virginia’s premier ultramarathon, hosted by West Virginia Mountain Trail Runners. The 21st edition centers at Canaan Valley Resort State Park in Davis, WV, and covers 40 miles primarily through the Monongahela Nati..

Event overview The MD Heat Trail Race is a trail running event at the Patapsco Pickall Area in Elkridge, MD. The event offers the following distances: 50K 25K On-site parking is adjacent to the pavilions and start/finish area at Shelter #..

The Inferno 5k & 10k, held at Dirt Farm Brewing in Bluemont, Virginia, offers a rugged forest-trail challenge for runners of all paces. The course is a loop behind the brewery, with the 5k completing one loop and the 10k two, featuring stee..

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..