Trail Running calendar near Montebello 2026-2027

A four mile vineyard run at Fables and Feathers in Goodview, VA on July 11, 2026, offered in-person and virtual. The event features a device free prediction run for prizes, a wine stopper medal, and winery tasting access for finishers.

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 run on the Massanutten range with 5,700 feet of climb, six aid stations (two water only), varied terrain and scenic overlooks, finishing with a post-run gathering at the Route 211 commuter lot.

A rugged 29.0 mile looped event in Crozet, Virginia on August 1, 2026, featuring five steep gravel laps and about 7,610 ft of elevation gain and loss. Entry is limited to 65 runners with a small fee and a waitlist.

A farm work inspired obstacle course at Waid Park on August 1, 2026, featuring more than 20 obstacles and new farm themed elements. Registration includes chip timing, a logo shirt and live bluegrass; kids 12 and under may participate free.

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.

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.

A 5 km and 10 km running event at Albemarle CiderWorks in North Garden, VA on August 30, 2026, with a cross-country course introduced for 2025 and both in-person and virtual entry options including medal and shirt choices.

The 53rd Winery 5K and 10K on September 5, 2026 takes place at Fifty-Third Winery & Vineyard in Louisa, Virginia. The event includes 5K, 10K and virtual options and benefits Hooves & Paws Animal Rescue.

Camp Bethel PEP! 5K Run/Walk is the tenth annual trail event at Camp Bethel in Fincastle, VA. The **5K** course runs across trails, fields, and forests on 470 acres and supports Camp Bethel through fees and sponsors.

Trail races at Douthat State Park featuring a roughly 13-mile loop used for a 50K, marathon, half marathon, and a six-mile race, with multiple aid stations, loop-based finisher rules, and limited field sizes.

A community running event in Farmville on September 12, 2026 offering in-person and virtual 5K and 10K races plus hand cycle divisions on a flat, crushed gravel out-and-back course along the High Bridge State Park Trail.

A multi-distance trail festival in the Shenandoah Valley with technical mountain courses through national forest. Distances range from 21K to 100M and the event offers qualification routes for UTMB World Series Finals and Western States.

Woodstock Warrior on September 19, 2026 is a multi-distance trail event at Seven Bends State Park near Woodstock, VA. The race uses a roughly 10 mile mixed-terrain loop with options up to 100 miles and a Last Man Standing Ruck.

Trail runs of 10 and 5 miles at Powhatan State Park during the Pawpaw festival, featuring riverside singletrack, open-field views, a water station near mile 5, festival amenities, and park lodging options.

Trail races on Cedar Mountain include canicross, a dog friendly 5k, a trail run without dogs, and a virtual option, with awards for top finishers and a traditional hunt breakfast.

A trail race at Brushy Hills near Lexington VA on September 19, 2026 offering 9 mile and 4 mile courses on single track. The event raises funds for Friends of Brushy Hills and local school track and cross country teams.

A 33.3 mile single loop trail run in the George Washington National Forest featuring a climb of Big Schloss with 360 degree views and three aid stations. Entry is limited to 60 runners and opens August 3, 2026.

A 110-mile trail ultramarathon in the Massanutten range with about 22,300 feet of elevation gain, a 48-hour limit, required second-half crew support, and multiple staffed and unattended aid stations.

A canicross and trail event on October 3, 2026 in Gordonsville, VA offering competitive 10K and 5K races, a 1.25 mile sprint, a casual dog friendly 5K, and a virtual 5K, with technical trails, three water stations, and a Finisher's Festival..