Trail Running calendar near Middle River 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.

A fall trail event at Trap Pond State Park featuring a 4.5 mile loop on the Bob Trail and a 2 mile walk. Participant fees support Legacy Academy.

Trail races of 50K and 20K at Rosaryville State Park in Upper Marlboro MD on November 14, 2026 feature a 9.5 mile perimeter single track, two aid stations, a nearby bag drop area, and awards for top finishers including military categories.

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 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, Maryland on November 21, 2026, featuring mostly single-track and horse trails, three stocked aid stations, awards for top finishers, and a no rain date policy unless support services cannot operate.

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 pre-Thanksgiving Turkey Trot at The Winery at Bull Run in Centreville, VA on November 25, 2026. Scenic **5 km** and **10 km** courses run through Manassas National Battlefield, with virtual entry options available.

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 5K at Autumn Lake Winery in Williamstown, NJ on Thanksgiving morning with dirt, grass, and sand underfoot. Awards for the top three male and female finishers, free entry for kids 14 and under, and a portion of proceeds support Lucky..

A cross country style 3 miles race at Anthony Campanella Park in Vineland, NJ, welcoming runners and walkers of varying ages. Awards for top overall finishers and multiple age groups; online registration with several payment options.

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.

A 5K at Eastern Regional Park on Thanksgiving Day, 11/26/2026, run over two laps of the park outer loop with paved and natural surfaces plus wooden bridges. Open to all ages; registration runs Aug 1 to Nov 1 for a $15 fee.

A community 5k run/walk and a separate competitive walking 5k at Killens Pond State Park on November 28, 2026. The event supports Milford High School Cross Country and features chip timing, awards, shirts, and post race refreshments.

Looped trail ultras in Prince William Forest Park offering 50K, 100K and 100 mile options on well-marked single-track 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..