Trail Running Calendar Virginia 2025-2026

Challenge yourself on the Massanutten Mountain Trails 100 Mile Run, a rugged trail ultramarathon in Virginia with more than 18,000 feet of climbing. Expect rocky singletrack, well stocked aid stations, and a 36 hour cutoff.

Run the Motion for Justice 5k in Rocketts Landing along the scenic Virginia Capital Trail with James River views. Enjoy a finisher medal and technical shirt or go virtual if you cannot attend in person.

Join the Fit Farmer 12K Trail Run on May 23, 2026 in Norton, Virginia, over scenic Flag Rock Area Trails from the Norton Reservoir Trailhead. Run for fresh air and community as proceeds support the Norton Farmers Market Senior Supplement pr..

Conquer the Cove features 25k and marathon trail races at scenic Carvins Cove with steep climbs, technical singletrack, and stocked aid stations. Limited to 300 runners on May 31, this rugged day promises a rewarding finish.

Join The Big Run Roanoke at Fallon Park for a scenic timed 5K on the Tinker Greenway plus a free kids fun run. Organized with Brooks and Virginia Amateur Sports, the race supports Smiles4Tab and features awards and a midpoint prize.

Run the scenic Dam Yeti ultramarathons on the Virginia Creeper Trail with 50 mile, 55K and 25K Pepsi Challenge routes over crushed gravel and across historic trestles. Finish at Sweetbay Brewing Co for a relaxed post race celebration.

Tackle the legendary Old Dominion 100, a 100 mile cross country endurance run near Fort Valley, Virginia with a history dating to 1979. Expect rugged mixed terrain, volunteer support and a silver buckle for finishes under 24 hour.

Join the Taskinas Creek Hike a Half on June 7, 2026 at York River State Park for an inclusive, no frills trail half that prioritizes fun over speed. Limited to 250 runners, scenic single track and a tough final two miles make for a memorabl..

Run under the stars in Prince William Forest Park at the OSS/CIA 50 Mile Night Run, honoring the park's OSS legacy. Choose 50 mile or 25 mile on a scenic single track loop with aid stations and true night race atmosphere.

Choose from marathon, half marathon, 10k, or 5k on the USATF certified Jackson River Scenic Trail in Covington Virginia, a mostly flat crushed gravel route with river views. Finishers receive commemorative medals and awards.

Test your limits at the Woodbooger 100 in Norton, Virginia on June 13 and 14 2026, with scenic trails, big elevation and lively local support. Choose from 100 mile, 100 km, 50 km or 25 km and chase a finisher buckle or custom medal.

Challenging mountain loop ultra near Galax VA with 50 and 100 mile options on a steep one mile course. Finishers earn a buckle and can enjoy on course aid, hot food, camping and outdoor showers for a supportive, rugged weekend.

Night Train is an evening trail run along the scenic High Bridge Trail in Farmville, VA, offering distances from 5K to 50K plus a family 5K option. Start and finish at Camp Paradise and enjoy a memorable finish across the bridge.

Windsor Castle Park hosts a low key, manually timed event on a shaded 3.1 mile loop in Smithfield, VA with 10 hour, 5 hour, 2 hour and 5k options. Stocked aid station, rucking option and handmade finisher items make for a friendly, challeng..

Run scenic trails at the Flag Rock 5K in Norton, Virginia on August 13, 2026. Part of the High Knob Outdoor Fest, this lively 5K supports the festival and showcases the Flag Rock Recreation Area.

Hit the forest trails at Dirt Farm Brewing on August 29, 2026 for the Inferno 5k and 10k. Tackle a scenic, technical loop, earn a finisher medal and a Dri FIT shirt, and toast with a glass of Dirt Farm beer. Virtual option available.

Take on the Odyssey Trail Running Rampage at Douthat State Park on September 12, 2026, with four loop distances from six miles to 50K on rugged trails with steep climbs. Expect chip timing, a performance shirt, finisher pint mug and post ra..

Take on a scenic 13.6 mile loop from High Knob Observation Tower through forest roads and sweeping views with about 1600 feet of climb. Proceeds support trail maintenance and the race is part of the High Knob Triple Crown.

Tackle the Hellbender 10K in Norton, Virginia on October 3, 2026, a challenging uphill 6.2 mile run that gains over 2,000 feet to the High Knob summit. Join fellow runners for the 13th annual climb and spectacular mountain views.

Explore scenic new hiking trails at Pocahontas State Park with options of a half marathon or 10k, both starting and finishing on the park's grass field. Pro chip timing and live results add a competitive edge to this fall trail run.