Trail Running calendar near Winchester 2025-2026

Event The Westover 5k & 10k takes place on October 18, 2025, at Bon Air Gardens in Arlington, VA. Distances offered: 5k 10k The event awards points toward the Year-Long 5k, 10k, and Back of the Pack Series, and toward the Fall Series...

2025 Wilderness Run 5k & 10k The event takes place on October 18 at Wilderness Run Vineyard in Spotsylvania, VA (11109 Plank Rd; GPS 38.325153, -77.719921). It features cross country trail courses with hills. The 5k is an out-and-back o..

Boulder Dash at Pinesburg Quarry is a running event hosted by Martin Marietta in Williamsport, Maryland. It offers a 5 Mile Challenge, a Family Friendly 5K, and a 1 Mile Fun Run for all levels. The 1 Mile Fun Run and 5K travel on rolling ro..

Run or walk the Franklin G. Schaeffer Memorial 5K at Wakefield Valley Park in Westminster for a scenic, traffic free paved trail experience. All paces welcome; early registrants get shirts and same day registration is available.

Run the Fall Backyard Burn at Lake Fairfax Park on Sunday October 19, 2025, choose 5.1 miles or 10 miles over flowing singletrack with about 300 to 600 feet of elevation. Expect aid stations, trail charm, and a lively post race vibe.

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..

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..

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..

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..

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.