Trail Running calendar near Annapolis 2025-2026

Run the scenic, historic trails of Patapsco Valley State Park at the Patapsco Valley 50K, offering 50k and 25k distances plus virtual options. Enjoy well stocked aid stations, commemorative shirts and unique finisher awards.

North Point Fright Night 5K & Haunted Trail is a Halloween-themed community event at North Point High School in Waldorf, Maryland, on October 25, 2025. The day features a 5K on the school’s official cross-country course (certified for compe..

Run a scenic 5K through woods and meadows on the paved trails of Quiet Waters Park in Annapolis, with costume fun and prizes. Proceeds support scholarships and children's camp programs, making every step count.

Get spooky on October 26 with the Halloween Horror trail run at Conway Robinson State Forest in Gainesville, VA. Choose 5k or 10k in person or virtual and enjoy a technical event shirt and finisher medal for all finishers.

Enjoy a scenic trail run along the Potomac at Riverbend Park with 5 mile or 10 mile options on mostly non technical singletrack and gentle hills. Proceeds benefit Homestretch and a kids program keeps it family friendly.

Event overview The Bobcat Trail Run is an 11-mile trail race held in Cunningham State Park in Thurmont, Maryland. The event starts and finishes at the Manor Parking Area near 6709 Cunningham Falls Park Rd. There is no race-day entry. Entran..

Tackle 50 miles of rolling single track on the scenic Seneca Greenway and Muddy Branch trails in Montgomery Village. This November ultramarathon blends rugged forest terrain, small stream crossings, and a close knit running community.

Honor Veterans Day with a scenic trail race at Rosaryville State Park near Upper Marlboro. Choose a rugged 50K or spirited 20K on buffed single track through rolling wooded trails with a small field and race day support.

Enjoy fall trail racing at Button Farm Living History Center in Germantown, MD with a half marathon, 10K, 5K and a free kids race benefiting Interfaith Works. Expect twisty singletrack, open farm field views, medals, post race food and awar..

Run through the vineyards at Barrel Oak Winery in Delaplane VA on November 15 with 3k and 6k options on a rolling cross country loop. Finishers enjoy a glass of wine, a medal and tech shirt plus chip timing and awards.

Talaria Trail Run is a fall trail event held at Trap Pond State Park in Laurel, Delaware. It features a 4.5-mile Race and a 2-mile Walk. The course follows the Bob Trail—a 4.5-mile loop around the 90-acre Trap Pond—winding through hardwood..

Run Of The Mill 5/10-miler walk/run trail runraiser takes place at Brandywine Creek State Park in Wilmington, Delaware (Hawk Watch Parking Lot, 41 Adams Dam Road, 19807). Participants choose a 5-mile or 10-mile marked course through Delawar..

Join the Fall Backyard Burn at Hemlock Overlook for scenic trail running along Bull Run with roots, rocks and stream crossings. Choose 5.2 or 9.5 miles and enjoy aid stations, race swag and a lively finish.

Event details The 2025 Herndon Turkey Trot is a cross-country style 5K held on November 22 at the Herndon Community Center, 814 Ferndale Ave., Herndon, VA. The race is open to participants age 4 and up. Runners must complete the 5K in 45 mi..

Event overview The Tuckahoe 25k takes place on Saturday, November 22, 2025, in Queen Anne, Maryland (13283 Cherry Ln). The race distance is 25k (15.5 miles) on trail terrain. The event is organized by the Centreville Crushers and Algonquin..

Join the Freeze Your Gizzard 5K or 1 Mile on Nov 22 at Ida Lee Park in Leesburg for a scenic but challenging cross country course and lively community vibe. Pre registered 5K runners receive a long sleeve shirt and the event supports Loudou..

Join the 10th running of Hex Hollow Half in Glen Rock PA, a scenic trail half marathon with rolling single track, roots and stream crossings. Enjoy decade old prices, an anniversary tee while supplies last, and support Olivia's House.

Run forest and meadow singletrack at the Fall Backyard Burn Trail Run at Laurel Hill, staged from the historic Workhouse Arts Center in Lorton VA. Choose one 5.4 mile lap or two laps for 10 miles and enjoy aid stations and post race food.

Run a scenic fall trail through Manassas National Battlefield from The Winery at Bull Run with 5k and 10k options, in person or virtual. Enjoy a postrace glass of wine and a finisher medal while supporting the Manassas Battlefield Trust.

Join the 21st Annual Catonsville High School Turkey Trot on Thanksgiving morning for a family friendly 1 Mile fun run and a competitive chip timed 5K in Catonsville, Maryland. All proceeds support the CHS cross country program.