Williamsport
Trail Running Calendar near Williamsport 2026-2027
Explore the top trail runs near Williamsport for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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.
A Halloween themed 5K at Adams County Winery on October 25, 2026, with chip timing, online results, and registration perks including a tee, wine glass, and finisher medal.
November 2026
An 11 mile out and back trail race in Cunningham State Park, Thurmont MD, with a single aid station at 5.5 miles and roughly 2200 feet of elevation gain.
A Thanksgiving themed 5 km run at Big Cork Vineyards in Rohrersville, Maryland, on November 14, 2026. The event is timed by J3 Timing and includes a t shirt, collapsible wine glass, finisher medal, and a wine pour.
A November event in Brunswick MD with a full marathon, half marathon, and a Veterans Challenge 5K that features towpath running, river crossings, and historic town sections.
Thanksgiving 5k and kids races at James Rumsey Technical Institute supporting local backpack programs and youth initiatives.
January 2027
A chip-timed 5k, 10k and half marathon on the flat C&O Canal Trail at Williamsport Park with a virtual option, medals, technical shirts and series points.
March 2027
Point of Rocks on March 7, 2027 features a mostly flat gravel out and back with 5k, 10k and half marathon options, limited water stations and a virtual option.
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 ultra in Knoxville MD where runners repeat a 4.167 mile loop each hour until one remains; a parallel 1 mile Mortals Edition runs under the same rules.
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.