Trail Running calendar near Chesapeake City 2025-2026

Blackout is an exciting nighttime 10K trail running event taking place in Emmaus, PA, organized by The Running Kind. Set against the rugged backdrop of South Mountain, participants will navigate a challenging course featuring over 1000 feet of elevation gain. The event encourages runners to embrace..

The Blues Cruise is a 50K Trail Ultramarathon celebrating its 20th anniversary, set to take place around Blue Marsh Lake near Reading, PA. The course features a diverse terrain, including rolling hills and a notable climb, with a strict 9-hour time limit, making it accessible for newer trail runners..

The Hainesport Endurance Run is a unique running event held at Hainesport Township Municipal Park, featuring multiple endurance challenges including 48-hour, 24-hour, 12-hour, and 100-mile races. Participants can run, walk, or crawl as many loops as possible on a certified flat paved path. The event..

The Rick O'Donnell Memorial 5 Mile Trail Run and Ultra Challenge is an annual event held in Mount Airy, Maryland, organized by the Frederick Steeplechasers Running Club. Taking place on October 12, 2025, it features three challenging race options: a 5-mile trail run, a 4-hour challenge, and an 8-hou..

BadgerPalooza is an ultra marathon event hosted by the Williamstown Badger at Autumn Lake Winery in Williamstown, New Jersey. Participants can choose from various race formats, including a 24-hour run, 12-hour run, and 6-hour run, with options for relay teams. The main event consists of running a 5K..

The MuleSkinner Endurance Races, set for October 18, 2025, in Upper Black Eddy, PA, features a variety of distances including a 50 Miler, 50K, Marathon, and Half Marathon. The course offers stunning views along the towpath, with modifications made for safety and accessibility. Participants can expec..

The Delaware Trail Fest is an exciting running event taking place at Lums Pond State Park in Bear, Delaware, on October 18, 2025. This festival celebrates the beauty of Delaware's trails and offers various race options, including a 12 KM trail, a 24 KM trail, a 12-hour Lone Wolf challenge, and a 12-..

The Patapsco Valley 50K is an annual trail running event held in Patapsco Valley State Park, Maryland, featuring both a 50K and a 25K race. Participants can choose to run in-person or virtually, with the virtual option allowing runners to complete their distance anytime between October 25 and Novemb..

WXT Ultra is an exciting running event taking place in Washington Crossing Park, NJ, featuring two challenging courses: a 50K and a 25K. The race begins and ends near the Camp Grounds and soccer fields, with the 25K primarily on single-track trails. The 50K course includes scenic routes through Bald..

The Rosaryville Veterans Day Trail Race, hosted by the Annapolis Striders, is a celebrated annual event taking place at Rosaryville State Park in Upper Marlboro, Maryland. This year marks the 15th edition of the race, featuring both 50K and 20K distances. The course offers a scenic and challenging e..

The MCRRC Stone Mill 50 Mile Run is a challenging trail running event set in Montgomery County, Maryland, showcasing the scenic Seneca Greenway and Muddy Branch trails. Participants navigate a primarily single-track dirt course featuring forested terrain and small stream crossings, with some areas p..

The Tuckahoe 25K is an exciting trail running event scheduled for November 22, 2025, in Queen Anne, MD. This race, organized by the Centreville Crushers and Algonquin Ultras Inc., offers a challenging yet accessible 25K course primarily on single-track and wider horse trails. Participants can expect..

The Hex Hollow Half is a running event taking place in Glen Rock, PA, featuring a half marathon (13.13 miles) and a shorter 6.66-mile option. The course, set in Spring Valley Park, offers a scenic experience through meadows, forests, and challenging terrain, including stream crossings and elevation..

The South Vineland Thanksgiving Run is a festive running event held at Anthony Campanella Park in Vineland, NJ. This cross-country style race welcomes participants of all ages and paces, making it a perfect way to celebrate the Thanksgiving holiday. The event features a 3-mile course and offers awar..

The 21st Annual Catonsville High School XC Turkey Trot is a cherished community event celebrating health and wellness. Scheduled for November 27, 2025, this event features a 1 Mile Family Fun Run and a 5K race, both of which are chip-timed. Participants can enjoy a family-friendly atmosphere while s..

The 27th Milford Cross Country Booster Reindeer Stampede 5k is set to take place at Killens Pond State Park in Felton, Delaware. This annual event features both a competitive walking category and a run/walk option, catering to participants of all abilities. Registration is available at a reduced fee..

The Frosty Looper 8-Hour is an exciting running event taking place at Cooper River Park, Pennsauken, NJ. This race features a fast and flat 3.75-mile loop, offering stunning views of the Philadelphia skyline. Participants have eight hours to complete as many laps as possible, with a focus on strateg..

Naked Nick is a trail running event taking place in Leesport, PA, featuring two distances: a 25K and a 50K. The race course runs along the scenic trails of Blue Marsh Lake, offering a mix of single track and gravel roads. Participants can expect a friendly atmosphere with awards for the top finisher..

The Mid-Maryland Trail Festival 50k is an exciting running event taking place in Elkridge, MD, featuring a challenging 31-mile course comprised of six loops through scenic wooded trails. Participants can choose to run the entire 50k solo or form relay teams of up to six members to share the distance..

The Matzah Miles 5k Trail Run and 1 Mile Family Walk is a festive event celebrating Passover, set to take place in Medford, NJ. Participants can choose between a competitive 5K trail run, a leisurely 1-mile family walk, or a fun 50-yard Kids Dash. The event features a pre-race warm-up, games for chi..