Trail Running calendar near Silver Spring 2026-2027

Running event at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offering a one mile fun run, a 5K, and a 5 mile race. The course runs in and around the quarry which will be closed for the event.

Timed trail event at Shenandoah River State Park where runners complete as many 3.48 mile loops as possible in 3, 6, 12, or 24 hour options. Supported aid, a hoodie, finisher awards, and a special 100 mile award are included.

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026, with in-person and virtual entry options. Walkers and strollers welcome and tiered registration pricing applies.

A trail run at Lake Fairfax Park in Reston, VA offering **5.1 mile** and **10 mile** singletrack courses with lake views, short technical sections, on-site bathrooms, a kids program, race swag, and optional finish medals.

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 ultradistance event in Patapsco Valley State Park near Baltimore on October 24, 2026, offering 50k and 25k distances plus virtual options through November 24. Race headquarters is at CCBC Catonsville, with aid stations and finishers..

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 5K, 10K and several 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 at Button Farm in Germantown, MD on November 7, 2026 feature twisty singletrack and open farm fields, with distances of 13.5, 6.7 and 3.2 miles. The event includes aid stations, portajons, finisher medals and post-race food.

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 races of **50K** and **20K** loop Rosaryville State Park single track in Upper Marlboro, MD, with two aid stations, a drop bag area, participant limit, and post race food and festivities.

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 3K and 6K at Barrel Oak Winery and Brewery in Delaplane, VA on November 15, 2026. In-person runs and virtual entry options are available; walkers and leashed pets are allowed.

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.

A trail 25k in Queen Anne, Maryland on November 21, 2026. Mostly single track with runnable hills, three aid stations, food options, and awards for the top three men and women.

A trail race at Riverbend Regional Park on November 22, 2026 offering 5 mile and 10 mile routes on riverside singletrack with aid stations, post-race food, parking, and a kids program.

A 5K and 10K on the flat Carderock trail along the Chesapeake and Ohio Canal Towpath in Potomac, Maryland on November 22, 2026. Walkers are welcome and virtual entries are available with medal and shirt options.

A 5 km and 10 km run at The Winery at Bull Run in Centreville on November 25, 2026, with routes through the Manassas National Battlefield trails and both in-person and virtual participation options.