Trail Running calendar near Herndon 2026-2027

Trail and virtual runs at Valor Ranch in King George VA featuring timed 10K and 5K events, a 10K ruck, a 1 mile fun run, and 100 percent of proceeds supporting Valor Ranch charitable programs.

Trail races in Rosaryville State Park offering 50K and 20K single-track loops, organized by the Annapolis Striders. The event is limited to 250 runners and includes aid stations, a drop-bag area, and time limits for each distance.

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.

Pre-Thanksgiving 3K and 6K runs at Barrel Oak Winery in Delaplane with in-person and virtual options; walkers and leashed pets are welcome.

BRRC GPS Cross Country 5K at Herring Run Park on November 15, 2026 features a cross country style start, mixed surfaces and two river crossings. Entry is free and donations are accepted.

A 25K trail race in Queen Anne, MD on November 21, 2026 with mostly single-track trails, three stocked aid stations, awards for top three men and women, and organization by Algonquin Ultras and the Centreville Crushers.

A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are re..

Experience riverside singletrack at Riverbend Park with 5 and 10 mile trail races. This event offers scenic Potomac River views, a dedicated kids program, and professional race support in a beautiful natural setting.

A 5K and 10K held on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD the weekend before Thanksgiving; virtual entries are available with options for medals and shirts.

A 5 km and 10 km trail race at The Winery at Bull Run in Centreville, VA, routed through the Manassas National Battlefield with virtual entry options.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

Thanksgiving morning 5K and 10K at Burke Lake Park with virtual options, medals, and a long sleeved technical shirt available.

Thanksgiving Day events at Sherando Park on 11/26/2026 include a 3.1 mile 5K plus a 100 m Tot Trot and two kids fun runs, each with specified registration windows and fees.

A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.

A 5K and 10K held in Wheaton Regional Park on November 26, 2026, featuring mixed gravel, trail, and paved paths plus virtual options with medal and shirt choices.

A 5K at Eastern Regional Park on Thanksgiving Day, 11/26/2026, run over two laps of the park outer loop with paved and natural surfaces plus wooden bridges. Open to all ages; registration runs Aug 1 to Nov 1 for a $15 fee.

Black Friday 5k and 10k at Frying Pan Park in Herndon on November 27, 2026, offering in person and virtual options plus onsite farm animals.

Trail and road races at Lake Anna State Park on November 27, 2026, offering 5K, 10K and half marathon distances plus virtual options.

A scenic Thanksgiving weekend 5K and 10K at Henway Hard Cider in Bluemont, VA on November 28, 2026, featuring post-race cider and virtual participation options.

Holiday-themed trail races at Burke Lake Park with 5K, 10K and half marathon distances plus virtual entries with medal and shirt options.