Trail Running calendar near Massanutten 2026-2027

Experience an ultra marathon through the Monongahela National Forest and Dolly Sods Wilderness Areas. Run across various terrains including boulder filled plains and ancient sphagnum bogs in the mountains of West Virginia.

An evening trail event on the High Bridge Trail near Farmville, VA offering 50K, Half Marathon, 5K and hiker and family options. The course follows an old rail trail, is chip timed, cupless, and requires runners to carry water.

A paired challenge on High Bridge Trail in Farmville, VA, combining Freight Train and Night Train events into combo distances from 26k to 150k, with a special award for completing a chosen combo.

Trail race on the Promised Land Trail behind Canaan Valley Resort offering a one-loop 5.9 mile and a two-loop 11.8 mile option. The field is limited to 200 participants and entrants receive a T-shirt and finisher medal.

A 12 hour trail event in Berkeley Springs WV on a scenic, technical five mile single track loop with about 750 feet of elevation change per loop. Aid stations, a post race meal, and handcrafted awards are part of the event.

Ruff Race at Snowshoe Mountain is a pet friendly 5k on July 5, 2026, taking place through the woods and the Village of Snowshoe. Participants may complete the course at any pace with their dogs.

A just under 50 km trail run in the southern Massanutten range with about 5,700 ft of elevation change, six aid stations, and a start and finish at the Route 211 parking area. 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 at 868 Estate Vineyards in Purcellville, VA on July 25, 2026 offering 5k and 10k routes plus virtual entry options and tiered registration fees.

A community trail event on July 25, 2026 at Locust Shade Park in Triangle VA offering 5K and 10K races plus virtual entries with medal or shirt options. Walkers are welcome and entry fees vary by registration period.

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.

A race day at Third Winchester Battlefield on August 8, 2026 offering 5K, 10K, and half marathon distances plus virtual options and tiered registration fees; walkers are welcome and courses pass through battlefield scenery.

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.

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.

Ridge Reaper 5k & 10k takes place on August 15, 2026 at Bull Run Marina in Clifton, VA, using the Bull Run Occoquan Trail. The event offers 5 km and 10 km in-person races plus several virtual entry options with medals and shirts.

A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, offering in-person and virtual options and included in the Sippin Series 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.

Trail-style 5K and 10K at Dirt Farm Brewing in Bluemont, VA on August 29, 2026, featuring rugged terrain, steep climbs, and virtual entry options with medals and shirts.

A 5k and 10k cross-country run at Albemarle CiderWorks on August 30, 2026, with virtual participation options. The course is new for 2025 and cider will be available after the event.

A road race at Fifty-Third Winery in Louisa, Virginia on September 5, 2026 offering 5K, 10K and several virtual options, with proceeds benefiting Hooves & Paws Animal Rescue.