Trail Running calendar near Hillsboro 2026-2027

A fall trail event in Little Orleans, Maryland offering a roughly 50K and 25K on forest trails with multiple aid stations and official cutoffs. Training runs take place in September and registration opens February 2, 2026.

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 at Rosaryville State Park in Upper Marlboro offer 20K and 50K on a 9.5 mile single track with wooded scenery, aid stations, a nearby drop bag area, and participant limits and time cutoffs.

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 pre-Thanksgiving running event at Barrel Oak Winery and Brewery in Delaplane, VA on November 15, 2026, offering 3K and 6K courses plus virtual entry options; walkers and leashed pets are welcome.

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 48 hour out and back ultramarathon inside Sideling Hill Tunnel near Valley-Hi, PA. Runners cover just under 160 miles in repeated 1.3 mile loops in complete darkness while a Toll Ticket system limits exits.

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, with scenic 5 km and 10 km courses through the Manassas National Battlefield. In-person races and virtual entries with medal and shirt options are 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 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 post-Thanksgiving running event at Lake Anna State Park offering 5 km, 10 km, and a half marathon with trail and paved sections. In-person and virtual participation options are available, and walkers are welcome.

Devil Dog Ultras is a loop trail event at Prince William Forest Park near Triangle VA offering 50K, 100K and 100 mile options 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..

A VHTRC holiday time 50k out and back on the Bull Run-Occoquan Trail from Hemlock Overlook to Fountainhead, with four aid stations and a GPX file for navigation. Entry includes lodge access, stocked aid stations, and a catered after party f..