Highfield-Cascade
Trail Running Calendar near Highfield-Cascade 2026-2027
Explore the top trail runs near Highfield-Cascade for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A community trail festival featuring a USATF certified 5 km loop at Furnace Run Park on August 29, 2026 with chip timing, variable surfaces and age group awards.
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
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.
October 2026
TrailFest in Shippensburg offers a half marathon, 5k, hike, 25 mile bike ride and a free 1 mile kids run while raising funds for the Cumberland Valley Rails-to-Trails Council.
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.
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
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.
A community fundraiser with a timed 5K, a 1.6K nature walk and a 500 m kids run supporting Toca Juniors Football Club and its Smiles Soccer Program.
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.
February 2027
A 50 km trail run at Hashawha Environmental Center in Westminster MD, featuring varied single-track, open fields, stream crossings and 5 aid stations. Entry for 2027 uses a lottery opening January 1, with indoor facilities and hot post-race food.
April 2027
A cross country 5K at Red Shedman Farm Brewery on the Linganore Winecellars grounds, with a technical quarter zip and one pour for finishers and on-site picnic and tasting options.
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.
July 2027
Three distance race in Shippensburg with a flat rail trail out and back, aid stations every two miles, finish line photos and post race food.