Trail Running calendar near Winchester 2026-2027

Harvest Hills on October 17, 2026 features 5K, 10K and a half marathon at Laurel Hill Park in Lorton, VA. Walkers are welcome and virtual entry options are offered with medal and shirt choices.

The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.

Marathon and half marathon at Fletcher's Cove on the C&O Canal Towpath, featuring a mostly flat, Boston-qualifying out-and-back course with riverside views, organized by the Safety And Health Foundation with cash and age-group awards.

Timed trail running at Shenandoah River State Park on a 3.48 mile loop with 670 ft of gain. Four time-based options from 3 to 24 hours, supported aid station, event hoodie, and awards including a special 100 mile recognition.

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026. Walkers and strollers are welcome and virtual race options are available with and without medals and shirts.

Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

Obstacle course races at Massanutten Resort on October 24 and 25, 2026, featuring 5K and 10K distances plus a kids race, spectator tickets, team entry options, lodging discounts, and service member discounts.

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 5K and 10K at Conway Robinson State Forest in Gainesville, VA on October 25, 2026. Walkers are welcome and virtual entry options with medals or shirts are available, with fees that vary by registration date.

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 race in Little Orleans, Maryland on November 1, 2026 offering 25K and 50K courses on mixed trail and road terrain, multiple aid stations, official cutoffs, training runs, and a series reward program.

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

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 in Rosaryville State Park offering 50K and 20K single-track loops, organized by the Annapolis Striders. The event is limited to 250 runners and includes aid stations, a drop-bag area, and time limits for each distance.

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 3K and 6K event at Barrel Oak Winery and Brewery in Delaplane, VA on November 15, 2026, offering in person and virtual entry options with medal and shirt choices. Walkers and leashed pets are permitted.

A 48 hour out and back ultramarathon inside the abandoned Sideling Hill Tunnel in Valley-Hi, PA. Runners complete 63 out and backs through a 1.3 mile corridor to cover just under 160 miles while managing darkness and limited exits.

A memorial race at Panorama Farms in Earlysville, Virginia featuring a 2 mile grassy trail and a free 800 m children's run. Proceeds support an annual scholarship for an Albemarle High School athlete.