Trail Running calendar near Annandale 2026-2027

A trail event at Conway Robinson State Forest Park on October 25, 2026, offering 5K and 10K in-person races plus virtual entries with medal and shirt options. Walkers are welcome.

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.

A backyard ultra scheduled for October 31, 2026 at Shawan Downs with repeated 4.167 mile loops. Runners complete as many loops as they can over a 24 to 48 hour period.

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 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 Rosaryville State Park in Upper Marlboro offer 20K and 50K on a 9.5 mile single track with wooded scenery, aid stations, a nearby drop bag area, and participant limits and time cutoffs.

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 in Delaplane offering in-person 3K and 6K races plus virtual options with medal and shirt choices; walkers and leashed pets are welcome.

A 5K cross country race at Herring Run Park on November 15, 2026, featuring mixed paved, field and technical single track surfaces. Entry is free and donations are accepted for scholarships and Friends of Herring Run Parks.

A 25K trail race in Queen Anne, Maryland on November 21, 2026, organized by Algonquin Ultras and the Centreville Crushers. The mostly single track course features runnable hills, rooty and muddy sections, three aid stations, and awards.

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.

A 5K and 10K held November 22, 2026, on the flat Carderock section of the C&O Canal Towpath in Potomac, MD. Walkers are welcome and virtual options with medals and shirts are available.

A pre-Thanksgiving trail event at The Winery at Bull Run in Centreville, Virginia on November 25, 2026. Offers 5 km and 10 km in-person races plus virtual categories with medal and shirt options.

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.

Lake Anna Turkey Trot at Lake Anna State Park on November 27, 2026 offers a trail 5K plus 10K and half-marathon courses that are half trail and half paved. Walkers are welcome and park entrance fees apply.

Devil Dog Ultras is a loop trail event at Prince William Forest Park near Triangle VA offering 50K, 100K and 100 mile options with staffed aid stations and set time limits. Entry is limited and the 100 mile requires a recent 50 mile finish.

Experience the beauty of Fountainhead Regional Park on a course featuring hiking trails and dirt roads. With two distance options and a dedicated program for kids, this event offers a complete day of trail running near the Occoquan Reservoi..