Thurmont
Trail Running Calendar near Thurmont 2026-2027
Explore the top trail runs near Thurmont for 2026-2027! We've gathered 22 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.
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.
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 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.
December 2026
Timed trail ultra on 12/05/2026 at Little Bennett Regional Park with 5 hour and 9 hour formats, relays, and a 4.5 mile race.
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.
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.
March 2027
8 hour timed trail event on a 5.5 mile loop at Little Bennett Park in Clarksburg, MD on March 6, 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
Memorial multi-distance event at Piney Run Park in Sykesville with a 5.25 mile loop, aid stations, commemorative posters, and awards.
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 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.