Trail Running calendar near Annapolis 2026-2027
We have found 127 Trailruns within 80 miles of Annapolis. See below where and when you can find the races.
0 – 100∞ km
Articles
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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.
February 2027
Support therapeutic riding programs while running through the beautiful forested trails of the Wicomico Demonstration Forest in this inaugural 5k trail race.
A 50 km trail run at Hashawha Environmental Center near Westminster MD featuring 31 miles of mixed surfaces, 5,800 feet of elevation gain, five aid stations and a 9 hour time limit. Lottery entry opens Jan 1, 2027 for ten days.
April 2027
A 14 mile untimed point to point trail run in King George, Virginia, routed mostly along the Dahlgren Railroad Heritage Trail through farmland and forest. The event is cupless, supports Sheetz For the Kidz, and features themed aid stations..
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.
May 2027
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.