Trail Running calendar near Hillsboro 2026-2027

The Woodstock Warrior will take place in Woodstock on Saturday 19 September 2026. You can run between 10 and 100 miles.

The River's Edge Endurance Challenge will take place in Brunswick on Saturday 26 September 2026. You can run between 5 and 6 hours.

Run with your dog at the Howlin' Coyote Canicross Trail Race in Caledon State Park, featuring varied terrain and a 10 km canicross plus a one mile Wild Pup dash. This non profit event supports Friends of Caledon and is disposable cup free.

A trail event on October 11, 2026 in Mount Airy, Maryland, offering a five mile run plus timed four hour and eight hour challenges. Net proceeds support the Frederick Steeplechasers Memorial Scholarship Fund.

Rocky Gap 25K and 50K trail events and relay options take place at Rocky Gap State Park on October 11, 2026. Courses use three distinct loops with singletrack sections, lakeside views, staffed aid at base camp, and on course water stations.

Trail races at Lake Fairfax Park in Reston on October 18, 2026 offering 5.1 mile and 10 mile singletrack courses with rocky and rooty sections, short climbs, parking at Pavilion G, and a supervised kids program.

A trail event at Patapsco Valley State Park offering in-person and virtual 50k and 25k options, Brooks shirts, aid stations, and distinct finishers awards, with headquarters at CCBC Catonsville. The park may postpone or move the race to vir..

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..

A scenic 5K through vineyard and farm terrain at Rocklands Farm Winery in Poolesville on October 25, 2026, followed by wine tastings, live music, and food vendors. The chip timed course uses dirt, gravel, and grass trails.

A trail ultra in Green Ridge State Forest on November 1, 2026, offering about 32.8 miles and 16.3 miles options on red and green trails with multiple aid stations, a midpoint oasis, and fall training runs.

Trail races at Button Farm in Germantown combine singletrack and open farm field running across 5K, 10K and half marathon distances, offered both in person and virtually. The event includes aid stations, finishers medals, awards and a chari..

An 8K cross country run at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The mixed terrain course loops through grapevines and hop yards and finishers receive a complimentary tasting.

Rosaryville Veteran’s Day on November 14, 2026 holds two races at Rosaryville State Park in Upper Marlboro, Maryland, with a 50K and a 20K. Event details and registration are listed via UltraSignup.

Trail races at Hemlock Overlook in Clifton, VA offer 5.2 and 9.5 mile options on hiking trails, dirt roads and fields along Bull Run, with rocky, root-strewn sections and designated spectator areas.

A trail race at Riverbend Park on November 22, 2026, offering 5- and 10-mile options along riverside singletrack with short hills; registration includes aid stations, post-race food and a race shirt, and a charity option supports Homestretc..

Run the scenic Turkey Trot at The Winery at Bull Run on Manassas National Battlefield with 5k and 10k options, in person or virtual. Enjoy a post race glass of wine, a finisher medal and tech shirt while supporting the Manassas Battlefield..

Run Thanksgiving at the 22nd Catonsville High School Turkey Trot featuring a chip timed 5K and 1 Mile Family Fun Run on a cross country course. Proceeds support CHS cross country and there are prizes; strollers and pets not allowed.

Devil Dog Ultras in Prince William Forest Park offers 100 mile, 100K and 50K loop races on primarily single track with staffed aid stations, set time limits, limited entry, and a multi year loyalty challenge.

Trail races at Fountainhead Regional Park on December 6, 2026, with 4.8 mile and 10.5 mile options along trails and dirt roads; aid stations, post-race food, optional medals, and a kids program are available.