Williamsport
Trail Running Calendar near Williamsport 2026-2027
Explore the top trail runs near Williamsport for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
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.
September 2026
Second annual 5K at Cacapon State Park on September 12, 2026 supporting the Humane Society of Morgan County with run, walk and virtual options and a free pup swim.
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.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.
October 2026
Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.
A scenic 5K trail run through rolling forest, single-track and gentle hills at Cacapon Resort State Park in Berkeley Springs, WV on October 11, 2026.
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.
April 2027
A 100 mile race on the scenic C&O Canal with an almost entirely flat course, starting and finishing at Camp Manidokan near Knoxville, Maryland, Apr 24 and 25 2027.
May 2027
The SCA 5K is a cross country 5 kilometer race on natural terrain held within Shalom Dutchfest. It offers multiple age divisions with medals, ribbons, and cash prizes, and early registrants receive a complimentary t shirt.
June 2027
A backyard style ultra in Knoxville MD where runners repeat a 4.167 mile loop each hour until one remains; includes a 1 mile Mortals Edition with a tie-breaker.
A 46th annual memorial five mile run on the C&O Canal Towpath in Williamsport MD with chip timing, awards, and a technical race shirt.