Trail Running calendar near Chesapeake City 2025-2026

Ultra Trail DE is a trail running event held at 2900 Montchanin Road in Wilmington, Delaware, set on private scenic trails owned by Longwood Gardens. The race features a challenging 6-hour format on a roughly 5-mile loop with about 700 feet of elevation gain per lap. The course offers a mix of creek..

The Conestoga Trail Run - 10 Tough Miles is a challenging and scenic trail race held annually in Holtwood, Pennsylvania. Known as the oldest trail run on the Conestoga and in the county for over 30 years, this 10-mile course features rugged, rocky terrain with steep hills, multiple small stream cros..

The Bear Trail Half Marathon & 10K is a trail running event held at Lums Pond State Park in Bear, Delaware. The race features two distances: a half marathon (13.1 miles) and a 10K (6.55 miles), both utilizing portions of the Little Jersey and Swamp Forest trails. The course offers a mix of single-tr..

Run-a-Muck is an annual 5K running and cross-country walking event held in the scenic Willistown countryside, supporting local land preservation. Participants can choose to run or "muck" through diverse terrain, making it a fun and challenging outdoor experience. The event features a lively atmosphe..

Blackout in Emmaus, PA, is a rugged nighttime trail running event hosted by The Running Kind. The 10K course features challenging, technical mountainous terrain with over 1,000 feet of elevation gain on South Mountain. Participants can choose the "Lights On" option, starting at dusk before darkness..

The Blues Cruise is a 50K trail ultramarathon held near Reading, Pennsylvania, celebrating its 20th anniversary in 2025. The 31-mile loop circles Blue Marsh Lake, featuring varied terrain including fields, rolling hills, single track, and less than half a mile of public road. The course includes a n..

The Hainesport Endurance Run is a multi-day ultramarathon event held at Hainesport Township Municipal Park in New Jersey. It features a flat, paved loop course of approximately 0.99 miles, certified by USA Track & Field, with an alternate 1.2-mile loop available if needed. Participants can compete i..

The Rick O'Donnell Memorial Ultra Challenge is an annual trail running event held in Mount Airy, Maryland, hosted by the Frederick Steeplechasers Running Club. The 13th edition takes place at Milkhouse Brewery at Stillpoint Farm and features three race options: a 5-mile trail run, a 4-hour challenge..

BadgerPalooza is an ultramarathon event held at Autumn Lake Winery in Williamstown, New Jersey. The main feature is a 24-hour race consisting of 24 consecutive 5K runs, starting at the top of each hour, totaling 74.4 miles. Participants can also choose 12-hour or 6-hour races, with individual or rel..

The Delaware Trail Fest, held at Lums Pond State Park in Bear, Delaware, offers trail running events for all abilities, celebrating the area's scenic outdoor trails. The race features distances of 12 km and 24 km, as well as a 12-hour Lone Wolf solo challenge and a 12-hour 4-person relay. The course..

The MuleSkinner Endurance Races take place in Upper Black Eddy, Pennsylvania, featuring distances of 50 miles, 50K, marathon, and half marathon. The course primarily follows the scenic, non-technical towpaths along the Pennsylvania side of the Delaware River, offering beautiful views and an easy tra..

The WXT Ultra is a trail running event held in Titusville, New Jersey, starting and finishing at Washington Crossing Park. It offers two distances: a 25K and a 50K. The 25K course features mostly single-track trails, including an 8.5-mile section within the park and short road segments.The 50K follo..

The Patapsco Valley 50K is an annual trail running event held at Patapsco Valley State Park near Baltimore, Maryland, with race headquarters at CCBC-Catonsville. The event features two main distances: a 50K and a 25K, both available as in-person or virtual races. Runners enjoy a scenic, historic, an..

The MCRRC Stone Mill 50 Mile Run is a challenging trail ultramarathon held in Montgomery Village, Maryland. The 50-mile course features scenic routes along the Seneca Greenway and Muddy Branch trails, traversing forested, rolling terrain primarily on single-track dirt paths. Runners encounter small..

The Rosaryville Veterans Day Trail Race, hosted by Annapolis Striders, is an annual trail running event held at Rosaryville State Park in Upper Marlboro, Maryland. The 16th edition in 2025 features two distances: a 50K ultra and a 20K race. Both courses loop around a 9.5-mile single-track perimeter..

Forbidden Run Fest is a trail running event held in Wissahickon Valley Park, Philadelphia, PA, celebrating one of the city's most scenic parks. The race offers three distances: 10K, 10 miles, and a Half Marathon+ (approximately 14 miles). The course features a mix of smooth gravel trails, compacted..

The Tuckahoe 25K is a trail running event held in Queen Anne, Maryland, offering a 25-kilometer (15.5 miles) course primarily on single-track and horse trails. The race features runnable hills, some rooty and potentially muddy sections, making it suitable for both first-time trail runners and those..

The Hex Hollow Half is a trail running event held in Glen Rock, Pennsylvania, starting and finishing at Spring Valley Park. It offers two race distances: a challenging half marathon of 13.13 miles consisting of two loops, and a shorter 6.66-mile single loop for those not ready for the full distance...

The South Vineland Thanksgiving Run is a cross country style race held annually at Anthony Campanella Park in Vineland, New Jersey. This approximately 3-mile event follows the well-known cross country course used by Vineland High School and the Vineland Grand Prix summer series. Open to runners and..

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..