Trail Running Calendar Maryland 2026-2027

Kick off the running year with this historic 5k at Kinder Farm Park. The mostly flat trail course features two gentle hills and is the first event in the Annapolis Striders Championship Series. Remember to bring your own water, as hydration..

This inaugural 5k trail race winds through the forested paths of the Wicomico Demonstration Forest in Maryland. Proceeds support therapeutic horseback riding services for the special needs community, with gift card prizes for top finishers.

Trail races in Columbia, Maryland along the Little and Middle Patuxent Rivers, offering 5K, 10K and half marathon distances with start and finish at the Guilford Pratt Truss Bridge. Registration includes a long sleeve shirt, finisher medal..

A club-based 10 miles race in Columbia, MD where runners score points for their RRCA club; awards are given by club and the event is part of the Maryland RRCA Grand Prix series.

Trail races near Leonardtown, MD on an ~10.5 mile loop around a 250 acre lake, offered as 17K, 34K, or 50K with two aid stations and a 100 runner limit.

The Hashawha Hills 50km features two loops of rolling trail, field, and woodland paths. Entry is via a lottery system with a unique, low-cost fee. All finishers earn a locally crafted pottery mug.

Trail races of 5 Miler, 10 Miler and a two person 10 Miler relay take place at Rockburn Branch Park in Elkridge on March 1, 2026; a portion of proceeds supports Bigfoot Endurance for Parkinsons research.

A 31 mile trail event at Rockburn Branch Park in Elkridge Maryland featuring six loops of about 5.179 miles. Relay teams of two to six can share the distance and an aid station is stocked with food and drinks.

Trail marathon and 50K on March 7, 2026 at Seneca Creek State Park near Gaithersburg, MD. Runners may stop at the marathon finish or continue to complete the 50K, and entries include a tech shirt and finisher medal.

A 5k and 10k at Smoketown Brewery on March 8 with out and back gravel courses, limited water stations, a virtual option, chip timing, a finisher medal, a technical shirt and a postrace beer.

A 10 mile trail race in Pocomoke State Forest on March 15, 2026. The event is cupless with one aid station, limited parking, and packet pickup available the day before.

HAT Run 50K in Havre de Grace, MD on March 21, 2026 is a 50K trail race with nearly 4,400 feet of climbing, a 3 mile start loop and two 14 mile loops, and four stream crossings that may result in wet feet.

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

Join The Husky Run 5K on the scenic Ma and Pa Trail in Bel Air. This walk and run event is open to all ages and abilities. Every finisher earns a limited-edition Husky medal.

Trail races at Rosaryville State Park in Upper Marlboro MD on March 28, 2026 include half marathon, 10K and 5K plus virtual options. Courses run through hardwood forests, fields and equestrian trails with multiple aid stations.

On March 29, 2026 in Severna Park, MD runners can choose a Marathon or Half Marathon mostly on the asphalt B&A Trail. USATF certified courses, staffed aid stations, finish medals, and participant quarter zips are provided.

Trail races of 5K and 10K take place at ThorpeWood private property in Thurmont, Maryland on April 4, 2026. Both are part of the FSRC Grand Prix, chip timed, with marked loops, on-site water and designated parking.

UltraTrax Wisp offers a scenic trek through Appalachian terrain at Wisp Resort. Choose from four distances up to 28 miles, with 10 hours to complete your chosen course. Finishers earn swag, and a post event celebration awaits at the base.

Run a meandering 5K trail race at Hopkins Farm Brewery for a good cause. This turtle derby-themed event raises funds for local wildlife conservation and encourages festive costumes. Enjoy a wooden finisher's medal and a lively after-party w..

A memorial trail event at Piney Run Park offering 50K, 25K, a 5.25 mile race and an 8 hour challenge on a 5.25 mile loop with aid stations and awards for top finishers.