Trail Running calendar near Winchester 2026-2027

Trail races in Columbia, Maryland along the Little and Middle Patuxent Rivers, offering 5K, 10K and half marathon distances with start and finish at the Guilford Pratt Truss Bridge. Registration includes a long sleeve shirt, finisher medal..

A club-based 10 miles race in Columbia, MD where runners score points for their RRCA club; awards are given by club and the event is part of the Maryland RRCA Grand Prix series.

Trail 5k and 10k races at Paradise Springs and Hemlock Overlook Park with series points, chip timing and a post race glass of wine. The 10k is two laps of the 5k technical route with multiple water stations.

The Hashawha Hills 50km features two loops of rolling trail, field, and woodland paths. Entry is via a lottery system with a unique, low-cost fee. All finishers earn a locally crafted pottery mug.

Trail races of 5 Miler, 10 Miler and a two person 10 Miler relay take place at Rockburn Branch Park in Elkridge on March 1, 2026; a portion of proceeds supports Bigfoot Endurance for Parkinsons research.

On March 1, 2026 at Wakefield Park in Annandale, the Spring Backyard Burn offers 5.5 mile and 10 mile trail race options across singletrack, doubletrack, stream crossings and minimal pavement. The event features aid stations, post race food..

A 31 mile trail event at Rockburn Branch Park in Elkridge Maryland featuring six loops of about 5.179 miles. Relay teams of two to six can share the distance and an aid station is stocked with food and drinks.

A women only trail endurance event near Triangle VA offering 50K and 25K options, two roughly 15 mile loops, five aid stations, and a limited field with a 9 hour cut off.

Tackle forest trails on a two lap loop at Conway Robinson State Forest. This winter 10k offers series points, a technical shirt, and supports pet rescue. Walkers are welcome, and a virtual option is available.

Trail marathon and 50K on March 7, 2026 at Seneca Creek State Park near Gaithersburg, MD. Runners may stop at the marathon finish or continue to complete the 50K, and entries include a tech shirt and finisher medal.

A 3k and 5k cross country event at Creek’s Edge Winery on March 7 with chip timing, finisher medal, technical shirt and a post-race wine option. Walkers and a virtual race option are available, and points count toward multiple series standi..

Run a 25K or 10K on the private trails of Panorama Farms in Virginia. The course is mostly wooded single and doubletrack with views of Naked Creek and the Blue Ridge Mountains. This event supports the local running community and is Trail Si..

A 5k and 10k at Smoketown Brewery on March 8 with out and back gravel courses, limited water stations, a virtual option, chip timing, a finisher medal, a technical shirt and a postrace beer.

A free International Women’s Day endurance day at Beaverdam Reservoir Park featuring a 7.5-mile loop and varied trail surfaces. The event centers women, offers course support through sunset, and focuses on movement and mutual support.

A trail race at the Workhouse Arts Center in Lorton on March 15, 2026, offering mostly singletrack through forest and meadows with options of roughly 5.4 miles or 10 miles. The event includes aid stations, optional medals, a kids program, a..

A cross country 4k and 8k around Twisted Oak Farm Brewery in White Post, VA with chip timing, water stations, and a virtual option. Points count toward multiple series including Back of the Pack and Sippin' Series.

A cross-country 5K and 1 Mile run at Wilderness Run Vineyards in Spotsylvania on March 21, 2026, featuring trail hills, on-site parking, a food truck and live music, drink tickets for adults, a 50/50 raffle, and awards across multiple age g..

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

A 41.4 mile trail ultra in Virginia's Shenandoah Valley featuring about 8,000 feet of climb, six fully stocked aid stations, notable natural landmarks, and a 125 runner field limit. Crews and pacers are not allowed.

A 50 mile trail run near Clifton, Virginia that follows forested, rolling terrain along Bull Run and the Occoquan River. The 2026 race is the 32nd running and features large bluebell stands and a Civil War theme.