Trail Running Calendar Maryland 2026-2027

A 5K cross country at Herring Run Park on November 15, 2026, featuring mixed surfaces and an XC style start. Entry is free and donations support a college scholarship or Friends of Herring Run Parks.

A 25K trail race in Queen Anne Maryland on November 21 2026 featuring mostly single track, runnable hills, three stocked aid stations, awards for top finishers, and no rain date.

A 5K and 10K held November 22, 2026, on the flat Carderock section of the C&O Canal Towpath in Potomac, MD. Walkers are welcome and virtual options with medals and shirts are available.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.

Experience the rolling hills of Fair Hill Natural Resource Management Area during this winter trail event. Choose between 25K or 50K distances on beautiful single track trails with heated facilities and fully stocked aid stations.

A trail 5K on February 20, 2027 at the Wicomico Ranger Station in Parsonsburg, MD that raises funds for 4STEPS therapeutic riding programs, with age/gender prizes in Amazon gift cards and a $32 registration fee.

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..

Genesee Valley Ultra is a timed loop trail event at Genesee Valley Outdoor Learning Center in Parkton, MD. Runners choose 24 hour, 12 hour, or 6 hour formats to complete as many laps as possible on a 2 mile loop, with chip timing and awards..

A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.

Run to Remember at Piney Run Park in Sykesville uses a 5.25 mile loop for 50K, 25K, a 5 mile race and an 8 hour challenge, with aid stations and commemorative gear included; proceeds support club programs and cancer research.

A 100-mile ultramarathon on the C&O Canal towpath near the Potomac River, featuring one 40-mile loop and two 30-mile loops, staffed aid stations, low-elevation terrain, and volunteer support.