Trail Running calendar near Oakton 2026-2027

Fall Run for the Wounded on Oct 18, 2026 features 5K, 10K and a half marathon through Prince William Forest Park with in-person and virtual options.

Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

A donation supported 5.25 miles trail race at Gunpowder State Park with a steep opening climb, single track sections, and on site race day registration.

Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.

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.

Trail run at Conway Robinson State Forest in Gainesville, VA offering 5 km and 10 km distances plus virtual options with medals and shirts.

Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.

The 5th Annual Mackyard Ultra is an ultramarathon hosted by the Baltimore Road Runners Club at Shawan Downs in Cockeysville on October 31, 2026. Entry is $20 and the field is limited to 100 runners with pre registration on RunSignUp planned..

Trail race in Little Orleans MD on November 1, 2026 offering 50K and 25K courses through Green Ridge State Forest with multiple aid stations.

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

A scenic trail 5k and 10k at Burke Lake Park on November 7, 2026, offering in-person and virtual options with medals and shirts available.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.

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.

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.

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

5K cross country at Herring Run Park in Baltimore with mixed terrain, free entry and donations accepted; the final GPS race of the year.

A 25K trail race in Queen Anne, MD on November 21, 2026 featuring single-track and horse trails, three aid stations, and awards for top finishers.

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..