Trail Running calendar near Winchester 2025-2026

The Historic Waterford Trail Run/Walk is an outdoor event taking place in Waterford, Virginia, on May 10, 2025. Participants can choose from a 5K Trail Run/Walk, a 10K Trail Run/Walk, or a Fun Run, all set against the scenic backdrop of Western Loudoun County. The course features a mix of trails, pa..

The Ed Poling Memorial PA Challenge is a demanding hiking event that covers over 20 mountainous miles on the Appalachian Trail in Pennsylvania, starting at Caledonia State Park and concluding at Pen Mar Park. Participants receive comprehensive support, including lunch, snacks, drinks, and transporta..

The Massanutten Mountain Trails (MMT) 100 Mile Run is a challenging ultramarathon held in the Massanutten Mountains within Virginia's Shenandoah Valley. Starting and finishing at Caroline Furnace Lutheran Camp in Fort Valley, VA, the rugged course features rocky trails and steep mountain climbs tota..

The Fountainhead Half Marathon and 10K Trail Run takes place at Fountainhead Regional Park in Fairfax Station, Virginia, just 30 minutes from Washington D.C. This challenging event features a half marathon of approximately 13.5 miles and a 10K of about 7.2 miles, both on rugged trails with rocks, ro..

The Night Raider 10k and 5k is a scenic trail run held at the Manassas National Battlefield, starting and ending at The Winery at Bull Run in Centreville, VA. Participants can enjoy a course that includes cross-country paths, dirt trails, a boardwalk, and gravel sections, with some hills. The event..

The Capital Backyard Ultra is an endurance running event held in Lorton, Virginia, featuring a unique format where participants run a 4.167-mile loop every hour until only one runner remains. The race supports experienced backyard ultrarunners aiming to push their limits, with a maximum of 60 partic..

The Ed Poling Memorial Hike for Hunger & Hope is a non-competitive fundraising event suitable for all ages, featuring hikes of varying distances along the scenic C&O Canal towpath in Maryland. Participants can choose from a 4K, 10K, or half marathon hike, catering to both casual and serious hikers...

The Barrel Oak 6k is a challenging cross-country running event held at Barrel Oak Winery in Delaplane, VA. Participants can choose between a 3k or 6k race, with the 6k being two laps of the 3k course. The event features scenic routes through vineyards, gravel roads, and hills.Runners receive a finis..

The More Miles Last One Standing Challenge is an annual ultramarathon event held in Knoxville, Maryland, featuring a unique "last one standing" format. Participants run a 4.167-mile course, starting each hour on the hour, and must complete the yard within that time to continue. The event also offers..

The Dash Through the Dirt event offers 5k, 10k, and half-marathon races at Carderock Recreation Area in Potomac, MD. The courses run along the scenic C&O Canal Towpath, featuring light gravel trails with minimal elevation changes, ideal for personal records. Participants receive a finisher’s coin, t..

The One Family Brewing 5k & 1-Mile event is a family-friendly race held at One Family Brewing in Lovettsville, VA. Participants can enjoy a scenic cross-country course around the brewery, with the 5k consisting of three laps around the brewery fields. Runners receive a beer, finisher’s medal, techni..

The Old Dominion 100 Mile Endurance Run is a challenging ultramarathon held in Fort Valley, Virginia, featuring a measured loop course through the Massanutten Mountains and Shenandoah River Valley. The race covers 100 miles with 14 significant climbs totaling 14,000 feet of elevation gain. Participa..

The Half Ass 25k & 10k is a challenging trail running event held in Newville, Pennsylvania, at 1599 Doubling Gap Road. The race offers two distances: a 10k with over 2,000 feet of elevation gain, and a more demanding 25k featuring over 4,000 feet of vertical gain, including iconic park highlights li..

The Crooked Run Valley 10k is a scenic and challenging trail race held at Sky Meadows in Delaplane, VA. Participants can choose between a 5k or 10k course, with the 10k being two laps of the 5k loop. The event features chip-timed results, finisher medals, and technical event shirts.It supports the c..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, known for its historical ties to the U.S. intelligence community. The race features a 50-mile course primarily on single-track trails, with some fire roads and crossings, run twice to complete..

The Highlands Sky 40 Mile Trail Run is a premier ultramarathon held annually in Davis, West Virginia, primarily within the Monongahela National Forest. Starting and finishing at Canaan Valley State Park, the challenging 40-mile course traverses rugged and scenic terrain including the Roaring Plains..

The Juneteenth Menare Foundation 12k & 6k is a scenic trail race held at Button Farm in Germantown, Maryland, celebrating Juneteenth. Participants can choose between a challenging 12k or a 6k course through the Schaeffer Farm Trails, with scenic and hilly terrain. The event features chip-timed resul..

The Canaan Valley Trail Run, scheduled for June 21, 2025, in Canaan Valley State Park, offers an exciting opportunity for runners of all levels. Participants can choose between a 5.9-mile single loop or an 11.8-mile double loop on the scenic Promised Land Trail. Each runner will receive a finisher m..

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is the opening race of the 14th annual Blue Crab Bolt Trail Running Series. Scheduled for June 21, 2025, it offers two trail race distances: approximately 5K (3.3 miles) with 200 feet elevation gain and 10K (6.4 miles) with..

The Catoctin 50k Trail Run is a challenging ultramarathon held in Cunningham Falls State Park near Frederick, Maryland. The race features a demanding out-and-back course on rocky, hilly trails through scenic forests and streams, with multiple aid stations providing water, snacks, and electrolytes. P..