Montgomery County
Trail Running Calendar near Montgomery County 2026-2027
Explore the top trail runs near Montgomery County for 2026-2027! We've gathered 69 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
A cross country 5K and 1 mile fun run at Ida Lee Park on November 21, 2026, with participant shirts, medals, post-race refreshments, and a food drive for Loudoun Hunger Relief.
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.
A festive trail event at Burke Lake Park offering 5k, 10k and half marathon options with chip timed results, a finisher medal, and a virtual race option.
December 2026
Timed trail ultra on 12/05/2026 at Little Bennett Regional Park with 5 hour and 9 hour formats, relays, and a 4.5 mile race.
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 Reservoir.
Multi-distance holiday race on the C&O Canal path in Georgetown and Fletcher’s Boathouse with in-person and virtual options and charity partnership.