Trail Running calendar near Montgomery County 2026-2027

Harvest Hills at Laurel Hill Park in Lorton, VA on October 17, 2026 offers 5K, 10K and half marathon distances with in person and virtual options and tiered entry fees; walkers are welcome.

The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.

Evenstar Ultras is a timed trail event at Shenandoah River State Park with 3, 6, 12 and 24 hour options on a 3.48 mile loop. Frequent returns to the main aid station reduce the need to carry heavy gear.

An in-person 5 km and 10 km event at Bluemont Park in Arlington on October 17, 2026, with flat courses and walker-friendly access. Virtual entries are available with several medal and shirt options.

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.

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 races of 50k and 25k take place in Patapsco Valley State Park on October 24, 2026 with in-person and virtual options. All entrants receive event apparel and a finishers award, and virtual runners have Oct 24 to Nov 24 to complete thei..

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 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.

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 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.