Trail Running calendar near Hillsboro 2025-2026

Run under the stars in Prince William Forest Park at the OSS/CIA 50 Mile Night Run, with 50 mile, 25 mile and 10 mile options on scenic single track and fire roads. Expect rugged trails, moonlit views and well stocked aid stations.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Run the scenic Third Winchester Battlefield on Aug 8, 2026 with 5k, 10k or half marathon options on mostly gravel trail. Chip timed event with finisher medal, tech shirt and virtual option, supporting Operation Enduring Warrior.

Take on the MD Heat Trail Race in Patapsco Pickall near Elkridge with 25K and 50K options on rolling, technical single track with river crossings and rewarding climbs. Relax at the finish with food, beer and a festive post race vibe.

Hit the forest trails at Dirt Farm Brewing on August 29, 2026 for the Inferno 5k and 10k. Tackle a scenic, technical loop, earn a finisher medal and a Dri FIT shirt, and toast with a glass of Dirt Farm beer. Virtual option available.

Join the Sasquatch Preservation Trail Run in scenic Seven Valleys, PA on September 12, 2026 for a fun 5K or 10K through rolling trails and forest scenery. Volunteers welcome to help keep this community event running strong.

Run to the Taproom at Creekside Farm Brewery in King George offers 5K and 8K trail runs through a scenic farm along the Rappahannock River. Finish with live music, food trucks and a complimentary beer for participants 21 and over.

Trails 4 Tails at Codorus State Park offers a scenic, rolling course for the 40 mile ultra, team relay or 25K with mixed singletrack, fields and lake views. Full aid station, camping and nearby lodging make it a fun day on the trails.

The Howlin' Coyote Canicross Trail Race will take place in King George on Saturday 3 October 2026. You can run 10 kilometers.

Run scenic, historic trails in Patapsco Valley State Park with 50k and 25k options plus virtual entries that include same shirt and award. Enjoy well stocked aid stations, volunteer support, and a festive finish near CCBC Catonsville.

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..

Fire on the Mountain features 50K and 25K trail races through scenic, rugged Green Ridge State Forest near Little Orleans MD on November 1, 2026. Registration opens Feb 2, 2026 and a fall training run on Sep 27 uses the red trail for roughl..

The Rosaryville Veterans Day Trail Race will take place in Rosaryville on Saturday 14 November 2026. You can run between 20 and 50 kilometers.

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.