Trail Running calendar near Stuarts Draft 2026-2027

The Big Run Roanoke on June 3, 2026 features a timed 5K and a free kids fun run at Fallon Park in Roanoke, VA. It marks the event's 10th year and serves as the official 5K for the Virginia Commonwealth Games.

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 community 5K on High Bridge Trail State Park featuring a flat, out and back course across the half mile High Bridge. Online registration, family pricing, and parking details are provided with proceeds supporting park programs.

Fox Trot 5k and 1 Mile at Merrie Mill Farm and Vineyard in Keswick on June 7, 2026 features a cross-country course, post-race cabana for participants, and a raffle with a gift basket valued at least $200.

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 USATF certified trail event in Covington, Virginia featuring a full marathon, half marathon, 10K and 5K along the crushed gravel Jackson River Scenic Trail. Finishers receive a commemorative medal and awards for top overall and age group..

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 10 miles out-and-back event at Smith Mountain Cooperative Wildlife Management Area in Sandy Level, Virginia on June 27, 2026. Three load options are available: LIGHT 10 pounds, STANDARD 25 pounds, and HEAVY 50 pounds.

An annual 5K and obstacle course hosted by EastLake Community Church in Moneta, Virginia on July 4, 2026, offering three event options. Proceeds support Smith Mountain Lake Christian Academy.

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 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 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.

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 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 5K and 10K cross country style race at Albemarle CiderWorks on August 30, 2026, with virtual entry options and post-race cider available at the venue.

A community 5K and 10K at Fifty-Third Winery & Vineyard in Louisa, Virginia that raises funds for Hooves & Paws Animal Rescue. The event offers in-person races and several virtual entry options with medal and shirt choices.