Trail Running calendar near Winchester 2025-2026

The Trails 4 Miles is an annual trail running event held at Sherando Park in Stephens City, Virginia. The main race is a challenging 4-mile course featuring mixed surfaces, including paved paths and wooded trails through the scenic Sherando..

Event details The Full Distance 5k & 10k takes place on October 11 at Locust Shade Park. Points from the event count toward the Year-Long 5k, 10k and Back of the Pack Series and the Sippin Series. A virtual race option is offered. Walke..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. T..

The Rick O'Donnell Memorial 5 Mile Trail Run & Ultra Challenge takes place at Milkhouse Brewery at Stillpoint Farm in Mount Airy, Maryland. In its 13th year, the event offers three ways to test endurance: a single 5-mile trail loop, a 4-hou..

Rocky Gap 25K, 50K, Relay Trail Run The event takes place on Sunday, October 12, 2025 at Rocky Gap State Park in Flintstone, MD (12500 Pleasant Valley Road, Flintstone, MD 21530). The program offers solo and relay entries for two distances..

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 the Fall Backyard Burn at Lake Fairfax in Reston on Oct 19, 2025. Choose a 5.1 mile lap or 10 mile option on mostly singletrack with roots, rocks and rolling climbs while supporting local nonprofit Homestretch.

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.

Event overview The Fall Backyard Burn Trail Run - Riverbend is scheduled for Sunday, November 2, 2025, at Riverbend Park in Great Falls, VA (8700 Potomac Hills Street, Great Falls, VA 22066). The event is produced by EX2 Adventures. Two cou..

Honor Veterans Day on scenic single track at Rosaryville State Park with Annapolis Striders, choosing 50K or 20K looped courses. Limited to 250 runners, this friendly trail race offers rolling climbs, aid stations, and awards.

Tackle the scenic MCRRC Stone Mill 50 mile trail run through forested single track on the Seneca Greenway and Muddy Branch in Montgomery Village. Enjoy rolling terrain, stream crossings and community spirit on November 8, 2025.

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..

Event The Schaeffer Half Marathon, 10K, 5K Trail Run is held on Saturday, November 8, 2025 at Button Farm Living History Center in Germantown, MD. The event is produced by EX2 Adventures and includes in-person races and virtual options for..

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..