Trail Running Calendar Maryland 2026-2027

A 25K trail race in Queen Anne, MD on November 21, 2026 with mostly single-track trails, three stocked aid stations, awards for top three men and women, and organization by Algonquin Ultras and the Centreville Crushers.

A 5K and 10K held on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD the weekend before Thanksgiving; virtual entries are available with options for medals and shirts.

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.

A 5K and 10K held in Wheaton Regional Park on November 26, 2026, featuring mixed gravel, trail, and paved paths plus virtual options with medal and shirt choices.

A 5K at Eastern Regional Park on Thanksgiving Day, 11/26/2026, run over two laps of the park outer loop with paved and natural surfaces plus wooden bridges. Open to all ages; registration runs Aug 1 to Nov 1 for a $15 fee.

An eight hour endurance run at Terrapin Nature Park where participants complete 2.8 mile laps to earn surprises placed in a personal stocking. Awards are given to the male and female with the most laps.

The Founders Half Marathon will take place in Potomac on Sunday 13 December 2026. You can run 13 miles.

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..

The RRCA Club Challenge will take place in Columbia on Sunday 28 February 2027. You can run 10 miles.

Riverside 8k and 16k in Potomac on February 28, 2027, with courses along the Potomac River and the C&O Canal path running north; nearby waterfalls and virtual participation options are available, and walkers are welcome.

The The Dark Side 8 Hour Ultra will take place in Clarksburg on Saturday 6 March 2027. You can run 6 miles.

The Hat Run 50K will take place in Havre de Grace on Saturday 20 March 2027. You can run 50 kilometers.

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.

A timed mountain trek at Wisp Resort offering 7, 14, 21, and 28 mile loop options with a 10 hour limit; well marked trails, optional weighted vests for bonus swag, and finishers receive a shirt, patch, and medal.

Run to Remember in Sykesville uses a 5.25 mile loop at Piney Run Park for 50K, 25K, a 5 miler and an 8 hour challenge. Fees include park entrance, a custom ice bandana and a commemorative mug.

The Spring Hops will take place in Mount Airy on Sunday 18 April 2027. You can run 5 kilometers.