Trail Running calendar near Middletown 2026-2027

Scenic 5 km and 10 km races through Burke Lake Park on October 31, 2026, with in-person and virtual entry options; walkers and strollers are welcome.

Trail race in Little Orleans MD on November 1, 2026 offering 50K and 25K courses through Green Ridge State Forest with multiple aid stations.

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.

A scenic trail 5k and 10k at Burke Lake Park on November 7, 2026, offering in-person and virtual options with medals and shirts available.

Trail ultramarathon at Sherando Lake VA on Nov 7 2026 offering 40, 20 and 10 mile courses across singletrack and mountain ridgelines with staffed aid stations.

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 5K and 10K at Walnut Creek Park near Charlottesville on November 8, 2026, with in-person and virtual participation and tiered registration fees.

Trail and virtual runs at Valor Ranch in King George VA featuring timed 10K and 5K events, a 10K ruck, a 1 mile fun run, and 100 percent of proceeds supporting Valor Ranch charitable programs.

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.

Pre-Thanksgiving 3K and 6K runs at Barrel Oak Winery in Delaplane with in-person and virtual options; walkers and leashed pets are welcome.

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.

A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are re..

Experience riverside singletrack at Riverbend Park with 5 and 10 mile trail races. This event offers scenic Potomac River views, a dedicated kids program, and professional race support in a beautiful natural setting.

Maryland Turkey Trot on November 22, 2026 at Carderock Park in Potomac MD offers 5k and 10k courses with virtual entry options; walkers are welcome.

A 5 km and 10 km trail race at The Winery at Bull Run in Centreville, VA, routed through the Manassas National Battlefield with virtual entry options.

Thanksgiving morning 5K and 10K at Burke Lake Park with virtual options, medals, and a long sleeved technical shirt available.

Thanksgiving Day events at Sherando Park on 11/26/2026 include a 3.1 mile 5K plus a 100 m Tot Trot and two kids fun runs, each with specified registration windows and fees.

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 trail-based 5K and 10K in Wheaton Regional Park on November 26, 2026, with in-person and virtual categories and points toward year-long series.