Trail Running calendar near Cockeysville 2026-2027

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.

Experience an off-road race weekend at Yeager’s Farm & Market featuring 4 and 10 mile trail runs. Enjoy a local atmosphere with post-race beer and bagels and earn a unique long sleeve tech shirt.

A six hour trail endurance challenge in Coatesville where participants run a 5K every hour for up to six rounds. Finishers earn patches or a medal and results feed a national leaderboard with championship prizes.

A 5K trail run at Kenbrook Bible Camp with a free kids fun run, awards including medal and gift card, and a pancake breakfast to support camper scholarships.

Nighttime 10 km trail run in Reading, PA where runners provide their own lighting and follow glow markers on rustic trails, finishing at the Liederkranz German club.

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 races in Rosaryville State Park offering 50K and 20K single-track loops, organized by the Annapolis Striders. The event is limited to 250 runners and includes aid stations, a drop-bag area, and time limits for each distance.

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 one day trail festival at Independence Park on November 15, 2026, offering multiple distance races, 3 hour and 6 hour lap events, and a 2 mile walk. Live music, food trucks, and local vendors support East Vincent Parks.

BRRC GPS Cross Country 5K at Herring Run Park on November 15, 2026 features a cross country style start, mixed surfaces and two river crossings. Entry is free and donations are accepted.

A 25K trail race in Queen Anne, MD on November 21, 2026 with mostly single-track trails, three stocked aid stations, awards for top three men and women, and organization by Algonquin Ultras and the Centreville Crushers.

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.

A 5K and 10K held on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD the weekend before Thanksgiving; virtual entries are available with options for medals and shirts.

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.

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.

A 5K and 10K held in Wheaton Regional Park on November 26, 2026, featuring mixed gravel, trail, and paved paths plus virtual options with medal and shirt choices.