Trail Running calendar near Warren County 2026-2027

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.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in Georgetown for the Christmas in July 5k and Half. Participants can choose between two race distances or join virtually from any location.

Trail races at Little Bennett Regional Park on August 1, 2026 feature a 3.7 mile 5K plus and a 6.2 mile 10K on twisty singletrack with hills and streamside sections. Staging is near the Prescott Horse Trailer Area in Clarksburg Maryland.

A small, early August looped event in Crozet, VA featuring five steep gravel laps totaling 29.0 miles and about 7,610 ft of elevation gain, limited entry, basic aid, and shuttle parking.

Experience a scenic out and back race on the mostly flat Dahlgren Railroad Heritage Trail. Choose between a half marathon or 50K distance and enjoy a well supported course featuring finishers medals and cash prizes.

Experience the scenic and historical landscape of Winchester Virginia with a 5k, 10k, or Half Marathon at Third Winchester Battlefield. Both runners and walkers are welcome to participate in person or virtually.

A remote trail event on routes near the Wild Oak Trail, held on a roughly 60 km course with a 50 km party option. The route has about 8,000 feet of climbing, limited aid stations, minimal course markings, and a restricted field size.

Experience the MCRRC Groovin Woodstock 7K XC at the Woodstock Equestrian Center in Maryland. This low key cross country race offers a scenic 7 km route for club members and non members alike.

Experience the Leopold’s Preserve 5k and 10k in Broad Run Virginia. This Sippin Series event welcomes both runners and walkers for a scenic race through the preserve in collaboration with the Farm Brewery at Broad Run.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

Conquer rugged terrain and steep inclines at Dirt Farm Brewing in Bluemont. Choose between 5k and 10k distances through breathtaking landscapes and enjoy a post race beer at the finish line.

Experience a cross-country run through the scenic grounds of Albemarle CiderWorks in Virginia. Choose between 5k and 10k distances or participate virtually followed by post-race cider at the orchard.

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

Experience a cross country race through Nottoway Park followed by a community picnic. This event features a three mile course and a kids fun run to celebrate the end of the summer season.

Run through the beautiful Fifty-Third Winery & Vineyard in Louisa, Virginia. This 5k and 10k event supports animal rescue and sanctuary efforts for local wildlife and farm animals.

A 71-mile, orange-blazed circuit on the Massanutten Trail with rugged, rocky terrain, multiple aid stations and two drop bag options, strict qualification and entry limits, and enforced cutoffs.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

A multi-distance trail running festival in the Shenandoah Valley offering 100M, 100K, 50K and 21K races on technical mountain terrain with UTMB World Series and Western States qualification.

The Final Countdown Tribute is a unique last-runner-standing event on a 1.33-mile loop at Amani Brewing. Each lap's time limit gets 20 seconds faster, testing endurance and pace. Runners receive a shirt, finisher award, and a post-race beve..