Trail Running calendar near Winchester 2026-2027

A trail run at Lake Fairfax Park in Reston, VA offering **5.1 mile** and **10 mile** singletrack courses with lake views, short technical sections, on-site bathrooms, a kids program, race swag, and optional finish medals.

A weekend of obstacle races at Massanutten Resort on October 24-25, 2026 with Sprint 5 km, Super 10 km and kids races on mountain trails featuring rocky terrain and steep climbs. Team entries can secure the same start time and eligible staf..

Andy's Backyard Ultra is a last person standing ultra at Teventrails in Earlysville, VA where runners complete a 4.17 mile loop each hour. The final finisher is the runner who completes one more lap than all other entrants.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

Trail races at Conway Robinson State Forest Park in Gainesville, VA on October 25, 2026 offering 5 km and 10 km courses plus virtual options with medal and shirt choices.

Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.

Trail running in Green Ridge State Forest near Little Orleans, MD, with 50K and 25K options. The 50K is about 31.95 miles out-and-back with seven aid stations; the 25K mixes technical trail and forest service roads.

Trail races at Button Farm in Germantown, MD on November 7, 2026 feature twisty singletrack and open farm fields, with distances of 13.5, 6.7 and 3.2 miles. The event includes aid stations, portajons, finisher medals and post-race food.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.

Trail races of **50K** and **20K** loop Rosaryville State Park single track in Upper Marlboro, MD, with two aid stations, a drop bag area, participant limit, and post race food and festivities.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre-Thanksgiving event at Barrel Oak Winery and Brewery offering in-person 3K and 6K races plus several virtual options; walkers and leashed pets are welcome and registration fees vary by entry type.

A 48 hour endurance event in Sideling Hill Tunnel where runners complete repeated 1.3 mile out and back laps totaling just under 160 miles. The format uses a toll ticket system and the field is limited to 96 entrants.

A trail race at Riverbend Regional Park on November 22, 2026 offering 5 mile and 10 mile routes on riverside singletrack with aid stations, post-race food, parking, and a kids program.

A 5K and 10K at Carderock Park on November 22, 2026, run on a flat, fast towpath. The event includes in-person and virtual options with medal and shirt choices.

A pre-Thanksgiving Turkey Trot at The Winery at Bull Run on November 25, 2026 featuring 5 km and 10 km courses through Manassas National Battlefield trails. Virtual entry options are available with different medal and shirt choices.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.

A post-Thanksgiving running event at Lake Anna State Park on November 27, 2026, offering a trail 5K, 10K and half marathon with mixed trail and road surfaces, plus virtual options that include medal or shirt choices.