Trail Running calendar near Dover 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.

A weekend of obstacle racing at Massanutten Resort with 5K and 10K courses, a kids race and spectator tickets. The mountain course uses rocky trails and steep climbs and lodging and service member discounts are available.

Andy's Backyard Ultra is a last person standing ultra at Teventrails in Earlysville, VA where runners complete a 4.17 mile loop each hour. The final finisher is the runner who completes one more lap than all other entrants.

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.

Fire on the Mountain on November 1, 2026 in Green Ridge State Forest offers two trail distances, about 32.8 miles and 16.3 miles, on red and green trails with technical sections, several aid stations, and a midpoint oasis.

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 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 laps while managing darkness and limited exits.

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.