Trail Running calendar near Dewey Beach 2025-2026

The Ripper - Sunrise to Sunset is a unique 14-hour and 6-minute timed trail running event held at the Pocomoke YMCA in Pocomoke, Maryland. Participants run a challenging 3.75-mile loop course, primarily single-track trails with rolling hills and rooty terrain, repeating as many laps as possible from..

The Race4Warriors Half Marathon is part of a larger event that includes 5K and 10K challenges, taking place in Lewes, Delaware. This event aims to support Wounded Warriors and homeless veterans while fostering connections between military and civilian communities. Participants can choose from variou..

The First State Trail Race, taking place in Wilmington, DE, offers a scenic and challenging experience for runners of all levels. Set in the picturesque Brandywine Creek State Park and First State National Historical Park, participants can choose from three distances: a 10K, 25K, or 50K. Each course..

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 competitive environment. The event includes a 5k run/walk and a c..

The Endless Summer 6-Hour Run is an annual endurance event held in Annapolis, Maryland, organized by the Annapolis Striders. Participants run for six hours on a 2.5-mile loop course that offers scenic views of Chesapeake Bay and the Bay Bridge. The event supports the Semper Fi Fund, with a portion o..

The Murderkill Ultramarathon is an exciting running event held at Killen's Pond State Park in Felton, Delaware. Participants can choose from three race options: a 50-mile, a 50K, or a 12-hour challenge, all set on a scenic 3.1-mile dirt loop trail. The course features a mix of shaded paths and gentl..

The Run the Vineyards Bohemia Manor Farm 8K is an exciting running event set in the picturesque Bohemia Manor Farm in Chesapeake City, MD. Participants can choose between a scenic 8K trail run and a 5K run, both featuring beautiful views of vineyards and the Bohemia River. The event includes chip-ti..

The Run the Vineyards - White Horse 10K/5K is an annual running event taking place at White Horse Winery in Hammonton, NJ. Scheduled for September 14, 2025, the event features a scenic 10K and 5K race, along with a 1-mile walk. Participants can enjoy a flat course through vineyards and country roads..

The Pemberton 24 is a unique 24-hour running event held in Salisbury, Maryland, featuring a series of 5K trail runs in The Pemberton Park trail system. Starting Friday evening, a 5K race begins every hour on the hour for 24 hours, allowing participants to run as many 5Ks as they choose, either solo..

Ultra Trail DE is a 10-hour trail running event held at 2900 Montchanin Road in Wilmington, Delaware. The race features a roughly 6-mile loop with about 700 feet of elevation gain per lap, set on private scenic trails that include creek crossings, singletrack, rolling hills, and unique landmarks lik..

The Bear Trail Half Marathon & 10K takes place at Lums Pond State Park in Bear, Delaware, featuring a scenic course that incorporates the Little Jersey and Swamp Forest trails. The event is designed for runners of all levels, offering a mix of single track and wide trails with relatively flat elevat..

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 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 Tuckahoe 25K is an annual trail running race held in Queen Anne, Maryland, organized by Algonquin Ultras Inc. The event features a 15.5-mile course primarily on trails, including single track and wider horse trails, with some hills, roots, and muddy sections. Runners can expect variable weather..

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 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 Algonquin 50K is a trail running event scheduled for February 7, 2026, in Pocomoke City, MD. This race offers a flat, fast course primarily on trails, making it ideal for both first-time ultra runners and experienced participants seeking a quick finish. The course features a modified out-and-bac..