Trail Running calendar near Dewey Beach 2026-2027

A 10-mile trail run through the pine and laurel of Maryland's Pocomoke State Forest. This cupless race has a 3-hour cutoff and limited parking, so plan ahead. The course is marked with arrows and flags for navigation.

The Montchanin Trails 5K is a trail run on March 29, 2026, at Longwood at Granogue in Wilmington, DE. The 5K course features single-track trails, hills, and varied terrain. Registration is limited to 300 participants and includes a t-shirt..

Run or walk a 5K trail race under the Flower Moon at Brandywine Creek State Park. This inaugural event supports local trail nonprofits and finishes with a moonrise celebration featuring s'mores and lawn games. Leashed dogs are welcome to jo..

Join this scenic 5k trail run at Parvin State Park featuring State Police unit displays and family activities to support the Alpha Corps Foundation.

USATF-certified 5K, 10K and half marathon events in Lewes, Delaware with Run, race-walk, or Heavy March (15 lb pack) options, a historical exhibit, and a post-race vendor and music area supporting Wounded Warriors and homeless veterans.

Explore the trails of Brandywine Creek State Park at the First State Trail Race. Choose from 10k, 25k, or 50k distances on a scenic course through rolling hills and farmland. It's a family-friendly event with an 8-hour time limit for all ru..

Join the 24th Dewey Beach Patrol 5K on June 14, 2026 for a scenic run along the bay that supports the Dewey Beach Patrol. Chip timing, age group awards, and a festive post race party with food and beer make it a must for local runners.

Run a technical 8K trail through vineyards and along the river at Bohemia Manor Farm. The chip timed event includes a tech shirt and wine glass. Celebrate after with a waterfront party featuring live music and food.

Run through scenic vineyard trails at William Heritage Winery on Labor Day weekend. Choose from a timed 5K, a 1-mile walk, or a kids' mile, with chip timing and awards for top finishers. After the race, enjoy live music, a food truck, and a..

The Pemberton 24 is a unique 24-hour challenge in Maryland's Pemberton Park. Runners and teams attempt to complete as many hourly 5 km loops as possible, earning points for each one. It's a test of endurance with a supportive camp atmospher..

Run through scenic vineyards and country roads at the White Horse Winery. Enjoy a flat course for a 10K, 5K, or 1-mile walk, followed by a party with live music and wine. All participants receive a tech shirt and souvenir glass.

Delaware Trail Fest celebrates the state's trails at Lums Pond State Park with a unique, fully age-graded race format. Choose from a 12-hour solo run, a 12-hour relay, a 24KM, or a 12KM lap course around the lake. All finishers get a sweats..

Experience a scenic trail run through the Assawoman Wildlife Refuge at the 23rd annual Mariners Bethel event featuring various distances and a post race bluegrass celebration.

Get ready for an adventure on the trails at Parvin State Park. Choose between a classic half marathon or a choose-your-own-adventure 6-hour ultra on a mostly flat, fast loop. The event features a cupless, carry-in/carry-out format, emphasiz..

The Talaria Trail Run is a fall event at Trap Pond State Park in Delaware. It features a 4.5-mile race on the scenic Bob Trail and a 2-mile walk. Participation supports Legacy Academy.

The Tuckahoe 25K returns for its 8th year on November 21, 2026. This 25-kilometer trail run features a mix of single track and horse trails with three fully stocked aid stations. The event proceeds rain or shine, offering awards and swag fo..

Enjoy a Thanksgiving 5K trail run through the scenic Autumn Lake Winery featuring dirt trails and grassy paths. This family friendly event supports animal rescue and welcomes strollers and leashed dogs on the course.

Experience a cross country Thanksgiving run at Vineland's Anthony Campanella Park. Open to all ages and paces, this event features awards for top finishers and supports the local public library.

Join the 28th annual Milford Cross Country Booster Reindeer Stampede 5k this November in Milford, Delaware. This long running community event features a 5 km race for all participants.

Event Overview The PHUNT 25K/50K Trail Race takes place on Saturday, January 16, 2027, at the Fair Hill Natural Resource Management Area in Elkton, Maryland. The start and finish location is the Edward L. Walls Activity Hall at the intersec..