Trail Running calendar near Leesburg 2025-2026

Run scenic, historic trails at Patapsco Valley State Park with 25K and 50K options, plus virtual entries for nationwide participants. Enjoy well stocked aid stations, post race food and a memorable finisher award.

Run For Your Life 5k is a cross-country 5K Run/Walk held at Verdun Adventure Bound in Rixeyville, Virginia (17044 Adventure Bound Trail). The race takes place on Verdun’s cross-country course across a 67-acre woodland setting, offering a tr..

RTB Fair Winds 5k/Fun Run is held at Quiet Waters Park in Annapolis, Maryland. The event offers a 5K, a Fun Run, and a Virtual 5K/Fun Run option. Runners traverse a fully paved course through woods and meadows, presenting a scenic park sett..

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..

Event The Halloween Horror event on October 26 takes place at Conway Robinson State Forest in Gainesville, VA. Distances offered: 5k 10k Walkers are welcome. A virtual race option is available. Points from the event count toward the 5k, 1..

Join the 4th annual Trailblazer Trot 5K and Monster Mile at CTEC to support scholarships for local students. Costumes are welcome for this festive Halloween fun run, and awards follow the 5K.

Tackle rugged trails and scenic ridgelines at Fire on the Mountain, a challenging 50K with a 25K option in Little Orleans, Maryland. Cooler November air and lively aid stations make this a fall must for adventurous trail runners.

Run scenic riverside singletrack along the Potomac at Riverbend Park with 5 or 10 mile options and moderate hills. Enjoy pro race support, post race breakfast burritos, swag and a supervised kids program with pre registration.

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.

Run scenic singletrack and open farm fields at Schaeffer Farms in Germantown on November 8, 2025, with half marathon, 10K and 5K options available in person or virtually. Proceeds support local nonprofit Interfaith Works.

The Barrel Oak Turkey Trot is a pre-Thanksgiving running event held at Barrel Oak Winery in Delaplane, Virginia. It features two race distances: a 3k and a 6k, with the 6k consisting of two laps around a cross-country course that winds thro..

Discover the Fall Backyard Burn Trail Run at Hemlock Overlook in Clifton VA on Nov 16, 2025. Choose 5 or 10 mile routes through scenic forest trails, stream crossings and rocky terrain for a fun, spectator friendly autumn challenge.

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..

Freeze Your Gizzard 5K and 1 Mile is held at Ida Lee Park in Leesburg, Virginia. Celebrating 23 years of running, this cross-country event offers a 5K through Ida Lee Park’s 138 acres and a 1-Mile Fun Run, starting and finishing near the pa..

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 rolling singletrack through the historic Workhouse Arts Center at Laurel Hill, choosing 5.4 mile or 10 mile courses. Enjoy scenic trails, on course aid, optional finish medals, and the chance to support local nonprofit Homestretch.

The Winery at Bull Run Turkey Trot offers a scenic trail 5k and 10k through the Manassas National Battlefield Park, starting and finishing near The Winery at Bull Run in Centreville, VA. The course is a cross-country style route across batt..

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.