Trail Running calendar near Woodstock 2026-2027

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.

A community fundraising trail event at Crozet Park offering a 5K, a limited 10K with a creek crossing, and a 0.75-mile family run. The day includes T-shirts, a pancake breakfast, a post-race festival, live music and proceeds for local trail..

Trail races at Conway Robinson State Forest on October 25, 2026, offering 5 km and 10 km trail distances plus virtual options with medal and shirt choices; walkers are welcome.

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.

Trail races in Little Orleans, MD, offering 50K and 25K courses through Green Ridge State Forest with mixed technical singletrack and forest roads, aid stations, cutoffs, training runs in September, and a finisher premium.

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.

Mountain Masochist Trail Run in Montebello Virginia on November 7, 2026 offers 100K, 50 Miler and 50K options over singletrack and forest roads. The loop starts and ends at Montebello Campground and includes multiple aid stations and campin..

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.

A trail running event on November 7, 2026 at Sherando Lake in Lyndhurst VA offering 40, 20, and 10 mile mountain courses with staffed aid stations, enforced cutoffs, drop bag rules, and postrace medal and technical shirt.

A fall trail event at Walnut Creek Park near Charlottesville offering 5K and 10K distances plus virtual participation options with various finish items and tiered registration fees.

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.

A memorial race at Panorama Farms in Earlysville, Virginia featuring a 2 mile grassy trail and a free 800 m children's run. Proceeds support an annual scholarship for an Albemarle High School athlete.

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, 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.

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.

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.