Trail Running calendar near Bentonville 2025-2026

The Bull Run Run 50 is a trail race of 50 miles scheduled for April 4, 2026, in Clifton, Virginia. The event is organized by volunteers from the Virginia Happy Trails Running Club and was established in 1993. The listed entry fee is $125 and a 13 hour time limit applies. Registration is planned to..

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. Walkers are welcome, and a virtual race option is available for r..

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 workout. Runners can choose between the 5k or 10k distances..

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 run, offering participants a scenic course winding through a..

April 18, 2026, Sip & Stride 5k & 10k returns to Southern Revere Cellars in Louisa, Virginia, for a winery-style cross-country race. The 5k is two laps and the 10k four laps around the winery property, featuring mostly flat terrain with no major hills. Seven water stations along the 10k and three on..

Mountain & Vine Vineyard 3k, 6k, & 9k takes place at Mountain & Vine Vineyards in Faber, Virginia (500 Delfosse Winery Ln.). The course loops the winery property: 3k is one lap, 6k two laps, and 9k three laps, delivering a hilly but scenic route with vineyard views. The atmosphere emphasizes a welco..

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 pets are welcome.Runners receive a glass of wine, a finisher’..

The C&O Canal 100 is a 100-mile ultramarathon held in Knoxville, Maryland, along the scenic C&O Canal towpath near the Potomac River and Appalachian Mountains. The course features one approximately 40-mile loop followed by two 30-mile loops, starting and finishing at Camp Manidokan. Runners enjoy a..

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 Series. A virtual race option is available. Walkers are permitted. Registere..

Farm Park Challenge is a trail running event at Agricultural History Farm Park in Montgomery County, Maryland, presented by My Muddy Shoes. The race offers multi-hour lap formats: 3-Hour, 6-Hour, and 10-Hour challenges, totaling 3, 6, or 10 laps, each start at the top of the hour and must be complet..

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, demanding endurance and technical footing. The race starts and fini..

The More Miles Last One Standing Challenge is an endurance running event held in Knoxville, Maryland, featuring a unique "last one standing" format. Participants run a 4.167-mile loop, known as "the yard," every hour on the hour, continuing as long as they can complete the distance within the hour...

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 unique event tests runners' versatility across multiple ter..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, a historic site once used to train World War II OSS spies. The race features a 25+ mile loop primarily on single-track trails, fire roads, and several bridge and road crossings, which runners c..

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 National Forest with sections on Timberline Ski Resort and the C..

The 3H Trail Half Marathon + DHRT 50K is scheduled for Saturday, August 8, 2026, in King George, VA (4224 University Drive, 22485). The event features two races: 3H Trail Half Marathon Dahlgren Heritage Rail Trail 50K Registration opens October 1, 2025. The half marathon fee is listed at $65 and..

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 steep climbs, exhilarating descents, and technical sections over..

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 route traverses forest trails with technical sections and mi..