Trail Running calendar near Annapolis 2025-2026

Valley View Hard Cider Challenge Half, hosted by Bishops Events, takes place at Valley View Farm in Delaplane, Virginia. The event offers 5k, 10k, and Half-Marathon distances on knotty courses that blend cross-country, trail, and hills. The 5k and 10k are out-and-back once, while the Half is out-and..

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 Grape Stomper Trail Run is a 5K event held on Friday, September 19, 2025, at Paradocx Vineyard in Landenberg, Pennsylvania. The course weaves through the Paradocx Vineyard grounds and nearby Crossan Park Trails, featuring single-track dirt trails, gravel, and grassy fields. The race blends trail..

The Bull Run Reunion Run 2025 is a 3-mile cross country race held in Parkton, Maryland, at Hereford High School. Scheduled for September 20, 2025, this event is part of the Bull Run Cross Country Invitational and is open to all ages. The Reunion Run is the seventh race of the day, offering participa..

The Cancer Warriors 5k is held in Belair, Maryland, on the Ma & Pa Trail. The in-person event features a simple out-and-back 5k course starting at the Ma & Pa Trail Head near Independent Brewery, with a second stream crossing, a fork near Route 24, and a turnaround near Tollgate Road before returnin..

9K for Semper K9 is a community running and walking event in Fredericksburg, Virginia, held at Old Mill Park along Canal Path by the Rappahannock River. The program includes a 9K race and a Kids .9 Mile Fun Run, welcoming runners, walkers, families. The course runs along canal paths in downtown Fred..

St. Anselm's Family 5k is a family-friendly fundraising race in Washington, DC, held at 4501 South Dakota Ave NE. The event covers a 5k distance on a double-loop trail course, suitable for runners and walkers alike.It benefits a memorial scholarship fund at St. Anselm's Abbey School, supporting stud..

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..

River's Edge Endurance Challenge is a nonprofit running event held at Brunswick Middle School, Maryland. The lineup includes a 5K (3.1 miles), a 3-Hour Endurance Race, and a 6-Hour Endurance Challenge. The largely trail-based course runs on the River's Edge Trail System, with about a mile on school..

Ultra Trail DE is a 6-hour trail running event held on private Longwood Gardens property at 2900 Montchanin Road in Wilmington, Delaware. Runners tackle roughly a 5-mile marked loop with about 700 feet of elevation gain per lap, featuring creek crossings, twisty singletrack, grass and gravel, and oc..

On Saturday, September 27, 2025, Red Devil 5K is a community cross-country race in West Grove, Pennsylvania, hosted at Avon Grove Middle School by Avon Grove High School. The rolling, three-loop course is mostly grass with some pavement and finishes on the track; it is the same course used by the AG..

THE Conestoga Trail Run - 10 Tough Miles is a rugged trail race held in Holtwood, Pennsylvania, along Kelly's Run and the Conestoga Trail. The 10-mile course combines rocky, hilly terrain with several stream crossings, offering scenic hilltop views of the Susquehanna River and Mountain Laurel. Runne..

Run to the Taproom - Creekside Farm Brewery 5K & 8K takes place at Creekside Farm Brewery in King George, Virginia. The event offers scenic 5K and 8K courses on a well-maintained dirt trail through a 1,000-acre farm bordering the Rappahannock River. It is chip-timed with awards for Top 3 Overall and..

Bear Trail Half Marathon & 10K takes place at Lums Pond State Park in Bear, Delaware, starting and finishing at Area 1. The course uses sections of the Little Jersey and Swamp Forest trails, combining single-track and wide trails with relatively flat elevation, making it approachable for runners of..

Hauser Hill Spiked Apple 5k takes place in Biglerville, Pennsylvania at the Hauser Hill Event Center, a 172-acre ridge-top venue in apple country. The chip-timed 5K Run/Walk starts and finishes at the winery on a cross-country course with uneven footing and gentle inclines, offering vineyard views a..

Quantico 24-Hour Walk, Run & Relay for Charity is held in Quantico, Virginia, benefiting Semper Fi & America's Fund, which supports wounded service members and military families. The event invites walkers, runners, and relay teams to cover mileage by doing laps or jogging several miles, with team an..

The Fall Harvest 5k is a scenic trail race held at Claude Moore Park in Sterling, Virginia. Set amidst the vibrant colors of autumn, the course features forest paths and leaf-covered trails, offering a picturesque experience for both runners and walkers. This event is part of the Run Your PRCS Parks..

Howlin' Coyote Canicross Trail Race, held in King George, Virginia (11617 Caledon Rd), offers two canicross options: a 10K Canicross and a 1-mile Wild Pup. This dog-friendly, non-profit event is part of the Friends of Caledon State Park series and supports natural resources and educational programmi..