Trail Running calendar near Chesapeake City 2025-2026

We have found 53 Trailruns within 80 miles of Chesapeake City. See below where and when you can find the races.

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is the opening race of the 15th annual Blue Crab Bolt Trail Running Series. Scheduled for June 21, 2025, it offers 5K (3.3 miles) and 10K (6.4 miles) trail races featuring scenic singletrack trails, lake views, and streams..

The Reckless Red Eye Endurance Run is a unique timed trail running event held in Columbus, New Jersey, at the Burlington County Fairgrounds. Scheduled for June 22, 2025, it offers 3-hour, 6-hour, 12-hour solo races, and a 12-hour team relay. The course features a flat, fast 3.3-mile loop on wide gra..

The 23rd Dewey Beach Patrol 5k is a road race held in Dewey Beach, Delaware, starting at North Beach Restaurant on McKinley Street. This USATF-certified out-and-back course runs through residential neighborhoods, offering a scenic and community-focused atmosphere. The event includes competitive walk..

The Coventry Woods Trail Running Festival, hosted by the Big Woods Running Club, takes place at Coventry Woods Park in Pottstown, Pennsylvania. Scheduled for June 22, 2025, the event offers five race options: 5K, 10K, 3-hour, 6-hour, and a 6-hour relay race. The courses feature mostly single-track t..

On The Rocks Trail Runs is a challenging trail running event held at Rocky Ridge County Park in York, Pennsylvania. The race features multiple distances: 50K, 33.3K, 16.7K, and 10K, all set on a course characterized by rolling hills, rocky terrain, dirt paths, and tree roots. Each loop includes appr..

July 2025

The Sweet Air Trail Race, organized by the Baltimore Road Runners Club, is a challenging trail run held at Gunpowder State Park in Sweet Air, Maryland. The course spans approximately 7 to 8 miles, featuring a mix of rolling hills, fast sections, water crossings, and occasional mud, providing a varie..

The Endless Summer 6-Hour Run, held annually at Greenbury Point Nature Center in Annapolis, MD, is a timed endurance event featuring solo and relay (3-person teams) categories. Participants run a 2.5-mile loop course that includes a scenic stretch onto Possum Point, offering views of the Chesapeake..

The Run the Vineyards Bohemia Manor Farm 5K & 8K is a scenic running event held at Bohemia Manor Farm Winery in Chesapeake City, Maryland. Participants can choose between a 5K run that winds through vineyards, along the Bohemia River, and wooded trails, or a more technical 8K trail run featuring sim..

The Murderkill Ultramarathon, held at Killens Pond State Park in Felton, Delaware, offers 50-mile, 50K, and 12-hour race options on a mostly dirt 3.1-mile loop trail. The course is relatively gentle with about 80 feet of elevation gain per loop, featuring shaded paths, some roots, rocks, and a footb..

August 2025

Loopy Looper is an ultra running event held at Cooper River Park in Pennsauken, New Jersey, featuring a fast, flat 3.75-mile paved loop with scenic views of the Philadelphia skyline and river. The race offers multiple distances including 12-hour, 24-hour, and a 101.25-mile ultra, as well as a 4-pers..

The Farm Fresh 5K & Kids Fun Run is an annual running event held at Miller Plant Farm, a working Century Farm located in York, Pennsylvania. The race features a rugged, all-terrain 5K course that includes paved and stone surfaces, grassy farm areas, and wooded trails, offering scenic views of the Le..

The RunPA Trail Jamboree is a family-friendly trail running event held at Camp Mack in Newmanstown, Pennsylvania. Scheduled for August 2-3, 2025, it features multiple endurance races including 12-hour, 6-hour, and 3-hour timed runs on a 3.4-mile loop course of single and double track trails with var..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running distances of 25K and 50K. The course features rolling single-track trails with over 2,000 feet of elevation gain, including technical rocky sections, two river crossings, and a short pav..

The Slopeside Slumber Party is a unique nighttime running event held at Roundtop Mountain Resort in Lewisberry, PA. Participants have three hours to complete as many laps as they can on a challenging 1.5-mile loop featuring 600 feet of elevation gain. The course includes 0.5 miles of pavement and 1..

The Run for Thorncroft & 1-Mile All-Ability Move-As-You-Please is a community health and wellness event held at Thorncroft Equestrian Center's 70-acre Farm in Malvern, PA. Featuring a 5K trail run, a 5K walk, and a one-mile move-as-you-please option, the event welcomes participants of all levels, in..

September 2025

The Sasquatch Preservation Trail Run is a trail running event held in Seven Valleys, Pennsylvania, featuring 5K and 10K race distances. Scheduled for September 6, 2025, the event offers participants a chance to run through scenic trails in a natural setting. While specific course details and atmosph..

Trails 4 Tails in Hanover, PA, is a trail running event held at scenic Codorus State Park, featuring a 5.72-mile loop course around Lake Marburg with single track trails and shoreline views. The event offers three race distances: a 40-mile ultra consisting of seven loops with approximately 4,200 fee..

The 13th annual Blood, Sweat & Tears Run in Mount Gretna, PA, promises to be an exciting event featuring three scenic courses along the Lebanon Valley Rails to Trails. This timed event ensures safety with police support and volunteers. Participants can look forward to post-run festivities, including..

The Run the Vineyards - White Horse 10K/5K is an annual running event held at White Horse Winery in Hammonton, New Jersey. Featuring flat and scenic courses through vineyards and country roads, the event offers 10K and 5K races along with a 1-mile walk. Participants enjoy chip timing with instant re..

The Cancer Warriors 5k is an annual running event held in Belair, Baltimore, MD, along the scenic Ma & Pa Trail. The course is a straightforward out-and-back route starting at the trailhead near Independent Brewery, featuring a path that crosses streams and passes under Route 24 before reaching a tu..