Trail Running calendar near Massanutten 2026-2027

Highlands Sky is a 40 mile trail run in Davis, West Virginia on June 20, 2026, centered at Canaan Valley Resort State Park. The route goes through Monongahela National Forest and Dolly Sods with meadows, bogs, and rocky plains.

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 race on a five mile single track loop in Berkeley Springs WV with technical terrain and about 750 feet of elevation gain per loop. Full aid at start and finish, awards and a 50 Mile Club recognition for 10 loops.

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 lakeside trail race at Boar's Head Resort in Charlottesville on July 11, 2026, featuring a 5.2 mile loop with about 745 feet of elevation change. The race is open to runners and walkers and is part of the Summer Trail Running Series.

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 vineyard run in Purcellville on July 25, 2026 offering 5k and 10k routes plus virtual entries with medal and shirt options. Registration fees vary by distance and registration date.

A July trail event at Locust Shade Park in Triangle, VA offering 5K and 10K distances plus multiple virtual options. The courses run on shaded, scenic trails and walkers are welcome.

A summer trail event in Crozet, VA listed as a 30 Miler with about 29.0 miles and 7,610 feet of climbing. The steep gravel out-and-back laps include limited aid, shuttle parking, and rugged summer conditions.

A running event at Third Winchester Battlefield on August 8, 2026 offering 5K, 10K and a Half Marathon. Virtual entries are available and 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.

The Dead of Summer 6K will take place in Jeffersonton on Saturday 8 August 2026. You can run 6 kilometers.

A 3.1 miles obstacle course through Thomas Jefferson’s Poplar Forest with elite, team, corporate and non-competitive waves. Entry fees support Poplar Forest education and elite competitors must complete all obstacles to qualify for prizes.

In-person 5K and 10K races run along the Bull Run Occoquan Trail at Bull Run Marina in Clifton, VA on August 15, 2026; virtual entries are available with different medal and shirt options and fees vary by registration period.

In-person 5K and 10K races at Leopold’s Preserve in Broad Run on August 23, 2026, with virtual entry options and registration tiers. The event is part of the Sippin Series in conjunction with the Farm Brewery at Broad Run; walkers welcome.

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.

A trail event at Dirt Farm Brewing in Bluemont offering 5K and 10K courses over rugged, hilly terrain on August 29, 2026. Virtual entries are available with medal and shirt options.