Trail Running calendar near Massanutten 2026-2027

A scenic loop at Sky Meadows State Park on May 31, 2026, offering 5K and 10K courses with views of fields, streams and Turners Pond. Walkers are welcome and virtual entries are available with medal and shirt options.

Experience the FXBG Trail 5 Miler at Motts Run Reservoir in Fredericksburg. This five mile trail race features three distinct climbs and over 300 feet of elevation gain along a scenic and flowing course.

A measured 100 mile loop in Fort Valley, Virginia, through the Massanutten Mountains and Shenandoah River Valley with 14 climbs and about 14,000 feet of elevation gain. There is a 24 hour cutoff for the silver buckle and 28 hours to finish.

A cross country 5K and 1 Mile at Merrie Mill Farm and Vineyard in Keswick on June 7, 2026, with in person and virtual options, a reserved post race cabana for participants, and a gift basket raffle.

A single-track trail race behind Zehmer Hall in Charlottesville covering about 3.1 miles, with steep climbs, technical footing, timing and bibs, and prizes for top finishers.

A night trail event in Prince William Forest Park offering a 50+ mile race made of two laps of a 25+ mile loop, plus 25M and 10M options. Aid stations are placed on course and crews are restricted to the Telegraph Road Pavilion.

A community 5K and 1 mile Fun Run in Warrenton, VA that raises funds for Fauquier Education Farm, a 501(c)(3) that advances agricultural education and donates its harvest to local food banks.

Experience a 40 mile ultramarathon through the Monongahela National Forest and Dolly Sods Wilderness. This trail run features the natural beauty of West Virginia with a route based around the Canaan Valley Resort State Park.

An evening trail event on the High Bridge Trail with 5k, Half Marathon, and 50k courses starting at Camp Paradise; the 50k features multiple aid stations, pacer allowances on the back half, and a course cutoff at Prospect.

A cumulative event pairing Night Train and Freight Train at High Bridge Trail State Park with multiple combined-distance options and a $15 Challenge fee that supports trail maintenance. Finish both distances in the same year to earn a uniqu..

A trail race in Canaan Valley State Park on June 27, 2026 with one loop of 5.9 miles or two loops for 11.8 miles on the Promised Land Trail, about 350 feet elevation gain per loop. Field is limited to 200 runners.

A 12 hour trail event on a scenic five mile single track loop in Berkeley Springs WV, featuring technical terrain with about 750 feet elevation per loop, on-course aid stations, a post race meal and handcrafted awards.

A pet-friendly 5k at Snowshoe Mountain on July 5, 2026, presented by The North Face. The route runs through the woods and the Village of Snowshoe and allows participants to run or walk with their dogs.

A roughly 50 km trail ultramarathon on the southern Massanutten range with about 5,700 feet of elevation gain, six aid stations, and a post run gathering at the Route 211 commuter parking lot. Entry is limited to 75 runners.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

A running event at 868 Estate Vineyards in Purcellville, VA on July 25, 2026, offering in-person 5 km and 10 km courses plus virtual entry choices with tiered fees.

In-person 5K and 10K at Locust Shade Park in Triangle, VA on July 25, 2026, run on shaded scenic trails. Virtual entries are also available and walkers are welcome.

A rugged out and back run near Crozet, Virginia covering about 29 miles with roughly 7,610 feet of climbing over five steep gravel laps. Limited to 65 runners, informal entry with a small fee and a waitlist.

A road and trail event at Third Winchester Battlefield in Winchester VA on August 8 2026 offering 5K, 10K, half marathon and virtual options. Walkers are welcome.

A memorial trail run in the Jefferson National Forest featuring a roughly 60 km course and a 50 km Party Route option, three aid stations, limited entry, and a largely unmarked route supported by a GPX file and turnsheet.