Boonsboro
Trail Running Calendar near Boonsboro 2026-2027
Explore the top trail runs near Boonsboro for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
An 11 mile out and back trail race in Cunningham State Park, Thurmont MD, on the Catoctin and Cat Rock trails with a single aid station at the 5.5 mile turnaround.
A scenic cross country 8K at Linganore Winecellars in Mt Airy, MD on November 8, 2026, featuring post race refreshments, awards and live music.
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 marathon weekend in Brunswick MD featuring a USATF certified full marathon, a half marathon and a Veterans Challenge 5K along the Potomac and C&O Canal.
A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are requested.
Thanksgiving 5k and kids races at James Rumsey Technical Institute supporting local backpack programs and youth initiatives.
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
5k 10k and half marathon on the flat C&O Canal Trail at Williamsport Park with chip timing, medal, technical shirt and a virtual option.
March 2027
An eight hour timed trail event at Little Bennett Park in Clarksburg, MD with a 5.5 mile loop where runners complete as many laps as they wish.
A chip-timed 5 km, 10 km and half marathon at Point of Rocks on March 7, 2027 with limited water stations, a virtual option, and finisher medals and shirts.
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 ultra in Knoxville Maryland where runners repeat a 4.167 mile loop each hour until one remains; includes a 1 mile Mortals edition and prize money.
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.