Trail Running calendar near Salisbury 2025-2026

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..

Run the Vineyards - Wind Vineyards 5K is a scenic trail race held at Wind Vineyards, 5178 Richmond Highway, Tappahannock, Virginia. The 5K route runs on well-groomed, hard-packed dirt and grassy trails across the 200-acre property, with two short hills and mostly flat sections. The event features ch..

The 5th Annual Darby Dash 5K Run/Walk, hosted by Seashore Striders, takes place at Cape Henlopen State Park’s Main Beach Parking Lot in Lewes, Delaware. The event offers a flat 3.1-mile course described as flat and fast: starting on the north side of the bathhouse parking lot, the route follows the..

Coastal Walk & 5K Run is a charity running and walking event held at Assateague State Park in Berlin, Maryland, located at 6915 Stephen Decatur Highway. Organised to support Coastal Hospice, it offers two options: a Coastal Hospice 5K Run and a Coastal Hospice 2 Mile Walk. The 5K course starts on a..

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..

North Point Fright Night 5K & Haunted Trail is a Halloween-themed community event at North Point High School in Waldorf, Maryland, on October 25, 2025. The day features a 5K on the school’s official cross-country course (certified for competition) with three race waves: Elite, Middle School & Younge..

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..

Rosaryville Veterans Day Trail Race, held in Rosaryville State Park in Upper Marlboro, Maryland, offers 50K and 20K trail distances on wooded perimeter single-track trails. The course features rolling hills with about 2,600 feet of elevation gain, mostly through deep woods and meadows, with scenic v..

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..

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 Trail Runs is an annual ultramarathon event held at Killens Pond State Park in Felton, Delaware. The race offers three distance options: a 50-kilometer, a 100-mile, and a 24-hour run, inviting endurance athletes to tackle different formats. The next edition is scheduled for Jan..

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 Half Marathon, held in Lewes, Delaware, begins and ends at American Legion Post 17. The event offers three Half Marathon challenges: Run, Race Walk, and Heavy March (a trail option with a 15 lb pack). The USATF-certified course winds through Cape Henlopen State Park and Fort Miles alon..