Chesapeake City
Trail Running Calendar near Chesapeake City 2026-2027
Explore the top trail runs near Chesapeake City for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
A single-loop 20 miles hike at Fair Hill Natural Resources Management Area on May 22, 2027 with aid stations, a finisher medal and about 1,600 feet of elevation gain.
5K at Harvest Ridge Winery crossing MD and DE through vineyards, wooded trail and country road, with live music, a food truck and complimentary wine and keepsakes.
June 2027
Five consecutive race days June 2–6, 2027 across DE MD PA NJ and NY offering marathon, half, 50K, 10K and 5K with daily aid stations and collectible medals.
August 2027
Trail races at Bohemia Manor Farm Winery with 5K and 8K courses through vineyards, riverfront and woods, chip timing, awards and a waterfront after party.
October 2027