Trail Running calendar near Middletown 2026-2027
We have found 142 Trailruns within 80 miles of Middletown. See below where and when you can find the races.
0 – 100∞ km
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A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.
A 3 mile cross country race through Nottoway Park in Vienna, VA on 08/30/2026 with a kids dash and a club picnic that includes food and drinks. Registration is free for members and $10 for nonmembers.
September 2026
Cross country at Morven Park with a high school invitational plus an open 5K, featuring food trucks, music and a spectator friendly course.
A 71 miles clockwise circuit of the orange-blazed Massanutten Trail with multiple aid stations, mandatory qualifications, and strict cutoffs on a rocky, high-ascent route.
Carderock Charge offers 5K, 10K and a half marathon on the flat C&O Canal Towpath in Potomac, MD on September 6, 2026.
A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.
A 5K and half marathon along the Chesapeake and Ohio Canal towpath in Georgetown with in-person and virtual entry options.
A second annual 5K at Cacapon State Park benefiting the Humane Society of Morgan County, offering in-person run and walk options plus a virtual entry. New course, awards ceremony, and a free post race pup swim in the lake.
A women only trail event at Fountainhead Regional Park offering a half marathon and a 10k plus on September 12, 2026. Registration runs June 8 to September 1 and two training runs are scheduled in August.
A 5K running race hosted by Hartwood High School Cross Country on September 12, 2026 in Stafford, VA. It is the first annual StallionsXC Open and serves as the opening race of the Stallion Invitational, with high school races afterward.
A stadium climb at Virginia Credit Union Stadium on September 13 honoring those lost on September 11 and supporting first responders and military. Climbers ascend sections 1 to 23 five times, with a wheelchair accessible concourse route ava..
A 5K cross country festival on September 15, 2026 at Franklin County Fair Grounds, with proceeds benefiting Shalom Christian Academy.
A multi-distance trail event in the Shenandoah Valley with technical mountain courses and qualification opportunities for UTMB World Series Finals and Western States.
The Final Countdown Tribute at Amani Brewing in Martinsburg WV uses a 1.33 mile loop where allowed lap time shortens each circuit, eliminating runners until one remains.
Races at Shenandoah River State Park on September 19, 2026 offering a half marathon, 10K, two 5K options and virtual entries with medal and shirt choices.