Trail Running calendar near Sterling 2026-2027

Looped 50K and 20K trail races at Rosaryville State Park near Upper Marlboro MD, single track woods, two aid stations, drop bag support and military awards.

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 run at Barrel Oak Winery in Delaplane offering 3K and 6K courses, virtual entry options, and walk and leashed pet access.

A free 5K cross country at Herring Run Park on November 15 featuring mixed surfaces, two river crossings, wooded trails, and donations accepted for local scholarships and park support.

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.

In-person 5 km and 10 km races on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD, with virtual entry options on November 22, 2026.

A 5 km and 10 km race at The Winery at Bull Run in Centreville on November 25, 2026, with in-person and multiple 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 run at Burke Lake Park offering 5K and 10K courses plus virtual options and a technical shirt guaranteed for registrations before November 13.

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.

Trail 5K and 10K in Wheaton Regional Park on November 26, 2026, with virtual options and series points for year-long and fall standings.

A Thanksgiving morning 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural trails; open to all ages, $15 registration fee.

A post-Thanksgiving outdoor event at Frying Pan Park in Herndon offering 5K and 10K routes plus virtual entry options and a post-race visit with farm animals.

A post Thanksgiving trail and road event at Lake Anna State Park offering 5K, 10K, half marathon and virtual entry options.

A Thanksgiving weekend 5 km and 10 km at Henway Hard Cider in Bluemont, VA with in-person and virtual options and post-race cider on the farm.

Ugly Sweater Dash at Burke Lake Park on November 28, 2026 offers 5k 10k and a half marathon on park trails, with virtual options and walkers welcome.

Trail loop ultras in Triangle VA offering 100 mile, 100K and 50K courses on mostly single-track terrain with stocked aid stations and set cutoffs.

Experience the beauty of Fountainhead Regional Park on a course featuring hiking trails and dirt roads. With two distance options and a dedicated program for kids, this event offers a complete day of trail running near the Occoquan Reservoi..