Trail Running calendar near Annapolis 2026-2027

A towpath race at Carderock Park in Potomac, MD on May 16, 2026, offering 5K, 10K and half marathon distances; courses are described as fast and flat, walkers are welcome, and virtual entry options include medal and shirt choices.

Trail races at Kelly's Run Nature Preserve in Holtwood on May 16, 2026 include chip timed 10K and 5K courses plus a free kids trail race of about 1.5 miles. The 10K features 1,256 feet of elevation and an aid station at Pinnacle Overlook.

Two days of fundraising hikes in May 2026 offer 5K and 10K canal routes plus 10 and 20 mile Appalachian Trail challenges, with trail support, fundraising matches, and proceeds benefiting Micah’s Backpack and the Refugee Welcome Network.

Test your resilience in this 24 hour endurance challenge in Annapolis. Set your own mileage goals to honor military heroes while enjoying provided meals and a community trail running environment.

A morning 5K held during the Fair Hill Scottish Games on May 16, 2026, with a $40 entry that includes game admission; on-site cash entries and ATMs are available, and cash prizes plus a trophy and Scottish claymore are awarded to top finish..

Experience the scenic beauty of the Brandywine Valley through forests and farmland. Choose between 10k, 25k, and 50k distances in this part of the USATF Mid Atlantic Off Road Series.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

An evening 5 km and 10 km run through the historic Manassas National Battlefield with start and finish at The Winery at Bull Run in Centreville, VA. In-person and virtual entry options are available.

Tough Mudder Philly on May 23, 2026 at Plantation Field offers 5K, 15K and Infinity obstacle runs with named obstacles, finisher items, spectator festival access, and group and volunteer options.

Furbutt's Backyard uses a 4.167 mile hourly loop with a 24 Hour 100 mile limit and a 12 Hour After Dark option at Mustang Trailhead. A single aid station supplies water, ice, Gatorade and snacks and crews are allowed there.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

A backyard ultra in Knoxville, Maryland where runners complete a 4.167 mile yard each hour until only one finishes. The event includes a 1-mile option, offers prize money for top finishers, and serves as a Backyard Ultra qualifier.

A 100-mile, 10-loop event on Rock Creek Trail near Washington D.C., with about 8,200 ft total elevation and a 36-hour cutoff. Two ticket types are listed at the same price including tax.

Trail run and walk on May 30, 2026 at Gentle Giants Draft Horse Rescue in Mt. Airy, MD featuring 1 mile and 5K courses across forest trails and open pasture with draft horses on the farm.

A community 5K and 1-mile walk in Lewes, DE on May 30, 2026 benefiting Rylie’s Smile Foundation, with in-person and virtual options, memorial signage along the Cape Henlopen State Park Trail, post-race pavilion activities, and chip timing.

A loop race at Sky Meadows State Park on May 31, 2026, offering 5 km and 10 km in-person distances plus virtual entry options, with a scenic course around Turners Pond featuring fields and streams.

Experience the FXBG Trail 5 Miler at Motts Run Reservoir in Fredericksburg. This five mile trail race features three distinct climbs and over 300 feet of elevation gain along a scenic and flowing course.

The Arc of Northern Virginia Community Challenge at Burke Lake Park on June 6, 2026 features a 5K race and a 2K fun walk and roll. Teams raise funds to support services and advocacy for people with intellectual and developmental disabilitie..

Trail Trotters 5K & Fun Run at Promise Landing Farm in Upper Marlboro offers a farm-trail 5K and a fun run to support the farm's riders and programs. The event includes free parking, a shirt deadline of May 16, no pets, and refunds up to se..

A night trail event in Prince William Forest Park featuring a 50 mile race made of two 25 plus mile loops, plus 25 mile and 10 mile options. The course is mostly single track with staffed aid stations and defined crew and pacer rules.