Trail Running Calendar Virginia 2026-2027

Run a scenic but technical loop trail at Sky Meadows. The event features a 5k and 10k, with finisher medals and chip timing. Points count towards multiple race series, and walkers are welcome.

Join the community for The Big Run Roanoke on June 3, 2026. Run a timed 5K on the Tinker Greenway or bring the kids for a free fun run at Fallon Park. The event benefits the local non-profit Smiles4Tab.

Trail ultras on the Virginia Creeper Trail offering a 50 mile, a 55K, and a 25K Pepsi Challenge with crushed gravel surfaces, aid stations, crew access points, cupless racing rules, and USATF certification for the 50 mile.

The Old Dominion is a classic 100-mile loop through Virginia's Massanutten Mountains and Shenandoah River Valley. With 14,000 feet of climbing over mixed terrain, it tests endurance against a 24-hour clock. It's a key event in the Grand Sla..

A community 5K on June 6, 2026 at High Bridge Trail State Park with an out and back route across the half mile High Bridge. Proceeds support park programs and participants receive a hat and finisher medal.

A mostly trail half marathon at York River State Park with a new no frills Hike a Half format. The route mixes single track, fire road and a short paved section, includes aid stations and limited entries for a smaller field.

A night-focused trail event at Prince William Forest Park offering a 50 mile race plus 25 mile and 10 mile options. The 50 mile uses a 25+ mile loop run twice and features staffed aid stations and specific crew and pacer rules.

Four race distances run on a USATF certified trail in Covington, Virginia, following an old railroad bed along the Jackson River. Mostly crushed gravel with light hills, on-course wildlife, finishers' medals, and awards for top overall and..

The Woodbooger 100 offers four distances from 25k to 100 miles in Norton, Virginia, across two days in June 2026. Early bird registration is available, and ultra finishers earn a distinctive buckle. The event features multiple award categor..

Event Overview The Fauquier Education Farm 5K and Fun Run is a fundraising event for the Fauquier Education Farm, a 501(c)(3) organization. The organization's mission is to advance agriculture through education and best practice farming. It..

A 50 and 100 mile ultramarathon near Galax, Virginia run on a one mile loop with about 500 feet of vertical gain per loop. Aid and hot food are provided each loop and onsite camping and shower facilities are available.

A three day trail running and camping getaway in the Virginia highlands. The package includes guided runs of 10 12 miles daily, campsite amenities, and a chance to unplug in the mountains. Meals and transport are self provided.

A night trail event on High Bridge Trail State Park near Farmville VA offering 50K, half marathon and 5K options including hiker and family entries. The course follows an old rail trail with aid stations, chip timing and a cupless policy.

The High Bridge Challenge pairs the Freight Train and Night Train on High Bridge Trail in Farmville, VA. Runners can combine distances across four combo options and receive a special handcrafted award for completing both races.

Run for up to 10 hours on a 3.1-mile trail loop in Windsor Castle Park. Choose from shorter timed races or try the rucking option. All finishers get a handmade medal and there are awards for the top performers.

Wine 4 Wildlife 4 Miler is a four mile vineyard event in Goodview VA with on-site and virtual options. Winners are chosen by closeness to a predicted finish time and all finishers receive a wine-stopper medal redeemable for a free glass.

A cross country 5k and 10k at 868 Estate Vineyards with chip timing, a virtual option, race awards, and a postrace glass of wine for participants.

A trail event at Hungry Mother State Park on July 25, 2026 featuring 8 Mile Race, 25k Race, and 8 Mile Hike with lake views, notable elevation gain, aid stations, medals, awards, and included race photography.

Timed trail races at Crystal Springs Recreation Area in Wytheville, VA include 12 hour, 6 hour and 3 hour Crystal Light options plus a limited Leftovers Option. The course is looped and aid stations are cupless with food provided.

Run a 5k, 10k, or half marathon on the scenic trail loops of the Third Winchester Battlefield. The event includes chip timing, a finisher's medal, and supports Operation Enduring Warrior. Walkers are welcome, and participation counts toward..