Trail Running calendar near Dewey Beach 2025-2026

Run the Vineyards at William Heritage Winery in Mullica Hill, NJ offers a 5K Run/Walk, a 1 Mile Walk, and a 1 Mile Kids Run on scenic vineyard trails. The scenic, chip-timed course features vineyard manicured trails with rolling hills, and a shared one-mile route for walkers and kids. Participants e..

Shootout XC Challenge 5K takes place at Gloucester County DREAM PARK, 400 US-130, Logan Township, New Jersey 08085. The event features a well-groomed all-grass cross-country course on a site that has hosted NCAA regional meets. The race serves as the opening event in the South Jersey XC Shootout, we..

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

Ramsey's Farm Pumpkin Run/Walk is a community running event in Wilmington, Delaware, held at Ramsey's Farm (440 Ramsey Road). The event features a 5K run/walk on off-road trails with uneven terrain and a free Kids Race for children 10 and under. It fosters a pumpkin-farm atmosphere with family-frien..

The Pemberton 24 is a unique endurance running event held at Pemberton Park in Salisbury, Maryland. Participants, either solo or in four-person teams, run multiple 5K races over a 24-hour period, with a new 5K starting every hour. The scenic trail course features an aid station stocked with refreshm..

The Kellie Thompson Shiley 5k and Family Fun Run is an annual event held at the Terrapin Nature Trail in Stevensville, Maryland, on the scenic Eastern Shore. It features a 5K trail run/walk and a 1-mile fun run for children aged 10 and under. The race honors Kellie Thompson Shiley’s competitive spir..

Ultra Trail DE is a 6-hour trail running event held on a private 550-acre Longwood Gardens property near Wilmington, Delaware (2900 Montchanin Road). Runners tackle a roughly 5-mile loop with about 700 feet of elevation gain per lap, featuring creek crossings, twisty singletrack, rolling hills, and..

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) consisting of two loops, and a 10K (6.55 miles) with one loop. The course utilizes sections of the Little Jersey and Swamp Forest..

BadgerPalooza is an ultra marathon hosted by the Williamstown Badger at Autumn Lake Winery in Williamstown, New Jersey. The centerpiece is a 24-hour challenge built from 24 laps of a 5K loop on winery grounds, totaling 74.4 miles for solo runners; 12-hour and 6-hour options are also offered, along w..

The Delaware Trail Fest, held at Lums Pond State Park in Bear, Delaware, is a trail running event celebrating the area's scenic outdoor trails. It offers multiple race options including 12 KM and 24 KM trail runs, as well as a 12-hour Lone Wolf solo challenge and a 12-hour 4-person relay. The course..

The 22nd Annual Mariners Bethel 6.2m & 3.1m Trail Run takes place at Camp Barnes in Frankford, Delaware. The flat, fast course begins and ends at Camp Barnes, winding through cross-country roads and trails in the Assawoman Wildlife Refuge. In addition to the 6.2-mile and 3.1-mile trail runs, there a..

RTB Fair Winds 5k/Fun Run is held at Quiet Waters Park in Annapolis, Maryland. The event offers a 5K, a Fun Run, and a Virtual 5K/Fun Run option. Runners traverse a fully paved course through woods and meadows, presenting a scenic park setting.The atmosphere is upbeat and community-minded, with cost..

Hot Mess Trail Races take place at Parvin State Park in Pittsgrove, New Jersey, in a collaboration between Endless Endurance and Second Capital Running. The event offers two options: a Half Marathon (two full laps of a 4-mile “lollipop” loop) and a 6-Hour Ultra (run as many laps as you can on the sa..

Talaria Trail Run is a fall trail event held at Trap Pond State Park in Laurel, Delaware. It features a 4.5-mile Race and a 2-mile Walk. The course follows the Bob Trail—a 4.5-mile loop around the 90-acre Trap Pond—winding through hardwood forests, crossing a dam at Raccoon Pond, and spanning boardw..

The Tuckahoe 25k is a trail race in Queen Anne, Maryland. It covers 25k (about 15.5 miles) on mostly single-track trails with some wider horse trails. The course is not overly technical but includes runnable hills, rooty, muddy sections, and varied conditions.Runners can expect three fully stocked a..

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..

Now in its 27th year, the Milford Cross Country Booster Reindeer Stampede 5k takes place at Killens Pond State Park in Felton, Delaware. The event offers a 5k run/walk and a competitive walking option, benefiting Milford High School Cross Country. The course, mapped in advance, emphasizes a family-f..

Angela Ivory Memorial Runs take place at Killen’s Pond State Park in Felton, Delaware, offering three distances: 50K, 100-mile, and a 24-hour race. The course is a 3.1-mile dirt loop contained within the park, featuring mostly flat terrain with a few roots and rocks and a short footbridge. Races are..

The Algonquin 50K is a Delmarva Peninsula trail ultramarathon held in Pocomoke City, Maryland, with start and finish at Milburn Landing in Pocomoke River State Park. The approximately 31-mile course is a modified out-and-back on mostly trail, including single-track and wider horse paths. It’s genera..

Race4Warriors 5K, 10K & Half Marathon Challenges is held in Lewes, Delaware, with all races starting and finishing at American Legion Post 17. The course weaves through Cape Henlopen State Park and Fort Miles, offering scenic coastal views near Rehoboth Beach. Distances include 5K, 10K, and Half Mar..