Trail Running calendar near Sterling 2026-2027

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026. Walkers and strollers are welcome and virtual entry options include medal and shirt choices.

Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

GPS Big Gunpowder Trail is a 5.25 mile trail race at Gunpowder State Park in Kingsville on October 18, 2026. The course includes a steep start, downhill and single track sections, and entry is donation based with race day registration avail..

A trail event at Patapsco Valley State Park with in person and virtual 50k and 25k options, event swag, aid stations, and a finishers mug or 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.

A trail event at Conway Robinson State Forest Park on October 25, 2026, offering 5K and 10K in-person races plus virtual entries with medal and shirt options. 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 of 50K and 25K in Green Ridge State Forest near Little Orleans MD on November 1, 2026. The 50K is an out and back with multiple aid stations; the 25K mixes technical trail and forest service roads.

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 near Upper Marlboro, MD. Courses run on a 9.5 mile perimeter trail through woods and meadows with aid stations, drop bags, and a strict no-headphones policy.

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 event at Barrel Oak Winery in Delaplane offering in-person 3K and 6K races plus virtual options with medal and shirt choices; walkers and leashed pets are welcome.

A 5K cross country at Herring Run Park on November 15, 2026, featuring mixed surfaces and an XC style start. Entry is free and donations support a college scholarship or Friends of Herring Run Parks.

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 November 22, 2026, on the flat Carderock section of the C&O Canal Towpath in Potomac, MD. Walkers are welcome and virtual options with medals and shirts are available.

A pre-Thanksgiving trail event at The Winery at Bull Run in Centreville, Virginia on November 25, 2026. Offers 5 km and 10 km in-person races plus virtual categories with medal and shirt 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.