Trail Running calendar near Wheaton-Glenmont 2026-2027

A donation-supported trail race of about 5.25 miles at Gunpowder State Park featuring a steep opening climb, varied downhills and scenic single track. It is the shortest event in the BRRC trail series and offers race day registration.

Trail ultramarathon at Patapsco Valley State Park offering 50k and 25k distances with in person and virtual options. Participants receive a Brooks event shirt, on-course aid stations, and a hand-thrown mug or finishers medal.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

Trail 5K and 10K at Conway Robinson State Forest in Gainesville, VA on October 25, 2026. Walkers are welcome and virtual entry options with medals or shirts are available, with fees that vary by registration date.

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.

The 5th Annual Mackyard Ultra is an ultramarathon hosted by the Baltimore Road Runners Club at Shawan Downs in Cockeysville on October 31, 2026. Entry is $20 and the field is limited to 100 runners with pre registration on RunSignUp planned..

A charity trail event at Gifford Pinchot State Park featuring a 5k run and a 3.5k walk with dog-focused awards, proceeds supporting canine cancer research, and a free children's dash for ages 10 and under.

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 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 3K and 6K event at Barrel Oak Winery and Brewery in Delaplane, VA on November 15, 2026, offering in person and virtual entry options with medal and shirt choices. Walkers and leashed pets are permitted.

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.

The Freeze Your Gizzard 5K - Leesburg will take place in Leesburg on Saturday 21 November 2026. You can run 5 kilometers.

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.