Derwood
Trail Running Calendar near Derwood 2026-2027
Explore the top trail runs near Derwood for 2026-2027! We've gathered 73 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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 chip timed 5k and 10k at Burke Lake Park on November 7, 2026, with trail and paved sections, finisher medal, technical shirt, and a virtual race option.
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.
Experience the natural beauty of Rosaryville State Park at this classic single track trail race featuring 50K and 20K distances through wooded meadows and rolling hills.
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 requested.
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 chip-timed 5 km and 10 km on the flat C&O Canal towpath at Carderock Recreation Area with medal, technical shirt, virtual option and series points.
A trail-based Turkey Trot at Winery at Bull Run in Centreville offering 5k and 10k options, chip timing, a finisher medal, a winery wine glass, and support for Manassas Battlefield Trust.
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.
Thanksgiving morning 5k and 10k at Burke Lake Park with chip timing, medals, long-sleeve shirts, a virtual option, and proceeds supporting Paws for Purple Hearts.
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 Thanksgiving morning 5k in Georgetown along the C&O Canal with chip timed results, finisher medal, long sleeve technical shirt, a virtual option and series points.
A timed trail and paved 5k and 10k at Wheaton Regional Park on November 26 with chip timing, a finisher medal, technical shirt and a virtual option.