Trail Running calendar near Warren County 2026-2027

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.

Harvest Hustle 5k and 10k takes place November 8, 2026 at Walnut Creek Park in North Garden with in person trail races and several virtual entry options.

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.

Looped 50K and 20K trail races at Rosaryville State Park near Upper Marlboro MD, single track woods, two aid stations, drop bag support and military awards.

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 run at Barrel Oak Winery in Delaplane offering 3K and 6K courses, virtual entry options, and walk and leashed pet access.

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.

In-person 5 km and 10 km races on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD, with virtual entry options on November 22, 2026.

A 5 km and 10 km race at The Winery at Bull Run in Centreville on November 25, 2026, with in-person and multiple virtual entry options.

Thanksgiving morning run at Burke Lake Park offering 5K and 10K courses plus virtual options and a technical shirt guaranteed for registrations before November 13.

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.

Trail 5K and 10K in Wheaton Regional Park on November 26, 2026, with virtual options and series points for year-long and fall standings.

A post-Thanksgiving outdoor event at Frying Pan Park in Herndon offering 5K and 10K routes plus virtual entry options and a post-race visit with farm animals.

A post Thanksgiving trail and road event at Lake Anna State Park offering 5K, 10K, half marathon and virtual entry options.

A Thanksgiving weekend 5 km and 10 km at Henway Hard Cider in Bluemont, VA with in-person and virtual options and post-race cider on the farm.

Ugly Sweater Dash at Burke Lake Park on November 28, 2026 offers 5k 10k and a half marathon on park trails, with virtual options and walkers welcome.

Trail loop ultras in Triangle VA offering 100 mile, 100K and 50K courses on mostly single-track terrain with stocked aid stations and set cutoffs.