Trail Running calendar near Annapolis 2026-2027

Enjoy a scenic trail 5k or 10k through Leopold's Preserve in Broad Run, Virginia on Aug 23, 2026, with chip timing, medals and a tech shirt. Walkers and virtual participants are welcome and races earn points toward year long series.

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 through Creekside Farm on scenic dirt trails along the Rappahannock River with 5K and 8K options, chip timing and awards. Celebrate after with live music, craft beer, a free pint for entrants 21 plus and food trucks.

Push your limits at the Pemberton 24, a 24 hour running challenge at Pemberton Park in Salisbury MD on September 18 to 19, 2026. Run hourly 5K loops solo or with a four person team, rest at your camp, and chase points and nightly bonuses.

Choose from a 25K, 40 Mile or 40 Mile relay on scenic mixed terrain at Codorus State Park, featuring lakeshore singletrack, open fields and historic sites. Enjoy a fully stocked aid station, race day picnic and finisher awards.

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.

Join the Kettle Cooker Five & Dime at Glenroy Preserve for scenic loop trails with 5 mile, 10 mile and 25K options over hills, creeks and rocky terrain. Chip timing, aid stations, a soft tee and post race beer make it a great day.

Scenic trail running at Milkhouse Brewery in Mount Airy with a 5 Mile race and 4 Hour and 8 Hour ultra challenges. Presented by the Frederick Steeplechasers to honor Rick O'Donnell and raise funds for local scholarships.

Scenic lake loop trail runs at Lums Pond State Park offer everything from a single lap 12 KM to a 24 KM and 12 hour solo or 4 person relay. Aid stations and race day bib pickup make it a relaxed fall challenge.

Experience scenic, historic trails of Patapsco Valley State Park with the 50K and 25K on Oct 24, 2026, offering in person and virtual options. Finishers earn special swag including a hand thrown mug for 50K completers.

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..

Run Schaeffer Farms singletrack in Germantown on Saturday, November 7, 2026 with half marathon, 10K and 5K options. In person and virtual entries welcome; proceeds support Interfaith Works for a fun, challenging trail day.

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.

Enjoy a crisp fall trail run at Hemlock Overlook, winding through forests, fields, stream crossings, and scenic Bull Run views. Choose a 5 or 10 mile course with plenty of spots for friends and family to cheer.

Run a rugged 25k through scenic single track and horse trails in Queen Anne, Maryland on November 21, 2026. Expect runnable hills, muddy rooty sections, three stocked aid stations, and a lively race vibe with swag and awards.

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.

Celebrate the season at Milford Reindeer Stampede 5k at Killens Pond State Park on November 28 with a scenic run or competitive walk. Enjoy a long sleeve race shirt, post race treats and chip timing in this family friendly holiday event.

Run scenic trails along the Occoquan Reservoir at Fountainhead Regional Park for the Fall Backyard Burn Trail Run. Choose a spirited 5 Mile or a challenging 10 Mile course with rolling climbs and great views.