Trail Running calendar near Annapolis 2025-2026

The ToM Opening Night VA is a cross-country kickoff hosted by Trials of Miles at Morven Park in Leesburg, Virginia. The event features a 5K cross-country race, with an open race for friends and family priced at $20. It’s designed to be spectator-friendly, offering a festival-like atmosphere on cours..

The High Rock Mountain Running Challenge is a Cascade, Maryland race starting and finishing at Pen Mar Park (14600 Pen Mar Rd). The course covers about 3.8 miles, including roughly 1.8 miles of ascent to High Rock Overlook before a descent back to the park for the finish. The route offers a pictures..

The Inferno 5k & 10k at Dirt Farm Brewing in Bluemont, Virginia, challenges runners with a forest-trail course behind the brewery. The 5k is a single loop; the 10k doubles back on the same path, featuring tree roots, rocks, and elevation changes that test footing and lungs. Expect steep climbs, rapi..

The Sasquatch Preservation Trail Run is a chip-timed 5K and 10K trail race held at South Branch Farms in Seven Valleys, Pennsylvania. Celebrating its 14th year, the event offers a scenic off-road course featuring varied terrain through farmland, woods, pastures, and streams, including a climb over t..

Located in Kennett Square, Pennsylvania at 760 Unionville Road, the WCU Cross Country Season Opener takes place on the Unionville High School grounds. The meet features men's and women's 5K races on a grass cross-country course that uses two 2K loops plus a 1K loop, with only short pavement crossing..

Trails 4 Tails in Hanover, PA, is a trail running event held at scenic Codorus State Park, featuring a 5.72-mile loop course around Lake Marburg with single track trails and shoreline views. The event offers three race options: a 40 Mile Ultra (7 loops, ~4,200' elevation gain), a 40 Mile Relay (team..

The VHTRC Women's Half Marathon will take place in Fairfax Station on Saturday 13 September 2025. You can run between 7 and 13 miles.

Athletic Equation will host its 18th Annual 12-Hour Adventure Trail Run at Prince William Forest Park, a 17,000+ acre, 40-mile trail reserve near Triangle, VA. The event covers 30 kilometers on a 6.5-mile looped figure-eight trail course, run for up to 12 hours with a two-person relay. The 100% trai..

The Creation House 5K Rugged Trail Run is a 5K trail race held in Littlestown, Pennsylvania (165 Christ Church Rd). It supports Creation House, a program designed to keep homeless families together as they rebuild their lives. The course is described as a beautiful, rugged nature run through farmlan..

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..

Grape Stomper Trail Run is a 5K trail race held at Paradocx Vineyard in Landenberg, PA. The course winds through Paradocx Vineyard grounds and Crossan Park Trails on dirt, gravel, and grass. Runners finish to a post-race celebration with music, snacks, and wine, with Paradocx Vineyard open for food..

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..

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 takes place in Brunswick, Maryland, centered at Brunswick Middle School and the nearby River's Edge Trail System. The in-person event offers three races: a 5K (3.1 miles), a 3-hour endurance race, and a 6-hour endurance race, all built around a 5-mile loop with about..

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 Conestoga Trail Run - 10 Tough Miles is a challenging and scenic trail race held annually in Holtwood, Pennsylvania. Known as the original and oldest trail run on the Conestoga, this 10-mile course features rugged, rocky terrain with steep hills, multiple small stream crossings, and beautiful vi..