Trail Running calendar near Keswick 2026-2027

A weekend of obstacle races at Massanutten Resort on October 24-25, 2026 with Sprint 5 km, Super 10 km and kids races on mountain trails featuring rocky terrain and steep climbs. Team entries can secure the same start time and eligible staf..

Andy's Backyard Ultra is a last person standing ultra at Teventrails in Earlysville, VA where runners complete a 4.17 mile loop each hour. The final finisher is the runner who completes one more lap than all other entrants.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

A community fundraising trail event at Crozet Park offering a 5K, a limited 10K with a creek crossing, and a 0.75-mile family run. The day includes T-shirts, a pancake breakfast, a post-race festival, live music and proceeds for local trail..

Trail races at Conway Robinson State Forest Park in Gainesville, VA on October 25, 2026 offering 5 km and 10 km courses plus virtual options with medal and shirt choices.

A 24 hour ultra at Riverside Park in Lynchburg, VA that uses a single 0.84 mile paved loop. Runners can enter solo or as a team and compete over a published 100 Miles distance while passing the same start and aid area each lap.

A timed, non competitive trail event at Wintergreen offering 7, 14, 21 and 28 mile loop options. Participants can add weighted vests, face a 10 hour cutoff for awards, and expect on site parking and finisher items.

Run on the flat, scenic Chessie Nature Trail near Lexington, VA with Marathon, Half, 10K, 5K, and a 26.2 relay. USATF certified courses, a virtual option, on-trail aid stations, finishers' medals, and post-race food are provided.

A mountain trail ultramarathon in Montebello, Virginia offering 100K, 50 miles and 50K routes across single track, dirt and gravel through the Blue Ridge, with start and finish at Montebello Campground and key aid stations on course.

Trail races at Walnut Creek Park on November 8, 2026 offering 5K and 10K distances plus virtual entries with medal and shirt options. Registration fees vary by entry type and by registration date.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre-Thanksgiving event at Barrel Oak Winery and Brewery offering in-person 3K and 6K races plus several virtual options; walkers and leashed pets are welcome and registration fees vary by entry type.

A pre-Thanksgiving Turkey Trot at The Winery at Bull Run on November 25, 2026 featuring 5 km and 10 km courses through Manassas National Battlefield trails. Virtual entry options are available with different medal and shirt choices.

A free Thanksgiving community event at Pocahontas State Park featuring a cross-country 5K and a short kids fun run. Registration is required; the day includes alumni photos, raffle drawings, and optional donations for a memorial award suppo..

Lake Anna Turkey Trot at Lake Anna State Park on November 27, 2026 offers 5k, 10k and half marathon courses. The 5k is a trail run while the 10k and half are half trail and half paved; walkers are welcome.

A looped trail ultramarathon at Prince William Forest Park with 50K, 100K and 100 mile options, staffed and unmanned aid stations, set time limits, a 300 runner cap, and a multi year loyalty challenge.

Trail runs at Fountainhead Regional Park on hiking trails and old dirt roads with 4.8- and 10.5-mile options, aid stations, post-race food, and a kids race and program for ages 2-11.

A VHTRC holiday time 50k out and back on the Bull Run-Occoquan Trail from Hemlock Overlook to Fountainhead, with four aid stations and a GPX file for navigation. Entry includes lodge access, stocked aid stations, and a catered after party f..

A set of in-person races on December 12, 2026 at Pocahontas State Park near Chesterfield VA offering 5K, 10K and a half marathon through the Bright Hope Trail area; walkers are welcome and virtual options are available.

A trail event at Burke Lake Park on December 24, 2026 offering 5 km and 10 km distances plus virtual participation. Walkers are welcome and registration includes tiered pricing and merchandise options.