Trail Running calendar near Annapolis 2026-2027

Experience the beauty of Fountainhead Regional Park on a course featuring hiking trails and dirt roads. With two distance options and a dedicated program for kids, this event offers a complete day of trail running near the Occoquan Reservoi..

A VHTRC holiday time 50k out and back on the Bull Run-Occoquan Trail from Hemlock Overlook to Fountainhead, with four aid stations and a GPX file for navigation. Entry includes lodge access, stocked aid stations, and a catered after party f..

A scenic trail event at Burke Lake Park on December 24, 2026, offering 5K and 10K distances plus virtual entry options with medals and shirts. Walkers are welcome.

A 31.7 mile New Year event in Prince William Forest Park run as three loops on groomed trails and some gravel roads. Unmanned aid at the start and finish is supplied by participants and entry is limited to 120.

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.

Experience a scenic out and back half marathon on the flat and smooth Dahlgren Railroad Heritage Trail. Enjoy a unique post race campfire with roasted donuts and earn a custom finisher medal.

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..

A backyard ultra in Lorton, VA featuring repeated 4.167-mile loops until one runner remains. The event offers close crew access, chef-supported aid, a 65-runner field, and rolling entry via Ultrasignup.

A 14 mile untimed point to point trail run along the Dahlgren Railroad Heritage Trail that starts at one Sheetz and finishes at another. The event features unusual aid station snacks and practical finisher swag.

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.

A last person standing endurance race in York, PA where runners repeat hourly loops until one remains. Entries include a designated parking and crew area, an event shirt, and a certified distance card.

A multi-distance event in Lewes, Delaware with 5K, 10K and half marathon options plus race walk and heavy march categories. The weekend includes an educational exhibit, vendors and live music while supporting wounded warriors and homeless v..

Tough Mudder Philly on May 22, 2027 offers 15K and 5K obstacle courses, an Infinity multi-lap option, spectator Mudder Village access, finisher items, group packages, and discounts for verified military and first responders.

A 24 hour Backyard format run on a 4.167 mile loop at Meadowood Special Recreation Area near Lorton, Virginia. Runners complete hourly loops with a 24 hour 100 mile limit and one shared aid station under a horse pavilion.