Trail Running calendar near Woodstock 2025-2026

Run rustic trails at the Crozet Trails Crew 5K, 10K, or Family Fun Run on Saturday October 25, 2025, at Crozet Park while supporting local trail building. Celebrate afterward with pancakes, live music and beer at the Trails Fest.

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..

Shenandoah Zombie Run is a 5K running event held at Camp Shenandoah in Swoope, Virginia. The course weaves through Camp Shenandoah’s hills and woods along Little North Mountain, offering forest trails as runners dodge zombies. Each particip..

Andy’s Backyard Ultra is a last-person-standing ultramarathon held at Teventrails in Earlysville, Virginia, about 14 miles northwest of Charlottesville. The event uses the Backyard Ultra format: competitors must complete a 4.17-mile lap wit..

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..

Test your limits at the Great Eastern Endurance Run at Sherando Lake in the Blue Ridge Mountains on November 1, 2025. Choose 10, 20, or 40 miles of rugged single track, jeep roads, and scenic ridgelines for a true mountain trail experience.

Mountain Masochist Trail Run - Montebello, VA (Nov 1, 2025) The event offers these distances: 100K 50 Miler 50K The event takes place in Montebello, Virginia, with the course beginning and ending at the Montebello Campground. The listed a..

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.

The Ultra Race Of Champions will take place in Lyndhurst on Saturday 1 November 2025. You can run between 13 and 50 kilometers.

Harvest Hustle 10k at Walnut Creek Park in North Garden, VA, offers a cross-country trail race with a 5k option as well. The course weaves through park woods with elevation changes, rocks and roots. The 10k features three water stations at..

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.

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.

Trail run through scenic singletrack and open farm fields at Schaeffer Farms with a half marathon, 10K and 5K on Nov 8 in Germantown, MD. Enter in person or virtual, support Interfaith Works and enjoy a finisher medal and after race fare.

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..

Autumn trail challenge at Hemlock Overlook in Clifton, VA along Bull Run with forest trails, creek crossings and wildlife. Choose 5.2 miles or 9.5 miles for a scenic, spectator friendly run supporting Homestretch.

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..

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..

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.