Trail Running calendar near Annapolis 2025-2026

We have found 57 Trailruns within 80 miles of Annapolis. See below where and when you can find the races.

The Dahlgren Heritage Rail Trail 50K is a challenging ultramarathon held in King George, Virginia, on August 2, 2025. This 31-mile race takes place on the Dahlgren Railroad Heritage Trail, a flat, well-maintained, and mostly shaded converted railroad bed featuring dirt, grass, pine needles, crushed..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running distances of 25K and 50K. The course features rolling single-track trails with over 2,000 feet of elevation gain, including technical rocky sections, two river crossings, and a short pav..

The Miner's Lady 8-Hour is an endurance running event held in Harpers Ferry, West Virginia, where the Blue Ridge Mountains meet the Shenandoah River. Participants run a challenging 10K loop featuring 850 feet of elevation gain, primarily on single-track trails that pass waterfalls and creek crossing..

September 2025

The Inferno 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features rugged forest terrain with technical sections including tree roots and rocks, along with notable elevation changes. The 10k race consists of two loops of a winding trail behind t..

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 distances: a 40-mile ultra consisting of seven loops with approximately 4,200 fee..

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.

The 12 Hour Adventure Trail Run takes place at Prince William Forest Park near Triangle, Virginia. This challenging event features a 6.5-mile figure-eight loop trail course with approximately 650 feet of elevation gain per loop, combining single track and fire road terrain. The course is designed to..

The Valley View Hard Cider Challenge Half is a scenic and challenging race held at Valley View Farm in Delaplane, VA. Participants can choose from a half marathon, 10k, or 5k course, featuring cross-country, trail, and hill segments. The event offers a festive atmosphere with a finish line cider, fi..

The Pemberton 24 is a unique 24-hour running event held in Salisbury, Maryland, featuring a series of 5K trail runs in The Pemberton Park trail system. Starting Friday evening, a 5K race begins every hour on the hour for 24 hours, allowing participants to run as many 5Ks as they choose, either solo..

The Cancer Warriors 5k is an annual running event dedicated to raising funds and awareness for cancer research. Scheduled for September 20, 2025, this event has successfully raised over $38,000 to support those affected by cancer. Participants can register as runners or "ghost runners," allowing ind..

Ultra Trail DE is a trail running event held at 2900 Montchanin Road, Wilmington, Delaware, on private property owned by Longwood Gardens. The race features a challenging 6-hour format where participants run multiple laps of a roughly 6-mile loop with about 700 feet of elevation gain per lap. The co..

The Conestoga Trail Run - 10 Tough Miles is a challenging trail race held in Holtwood, Pennsylvania, known for its rugged terrain and scenic views. Celebrating over 30 years, this event features a hilly course with rocky paths and stream crossings, making it suitable for experienced trail runners ag..

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 13.1-mile half marathon consisting of two loops and a 6.55-mile 10K with one loop. The course utilizes portions of the Little Jersey and Swamp Forest trails,..

October 2025

The Full Distance 10k and 5k is a scenic trail race held at Locust Shade Park in Triangle, VA. Participants can choose between a 5k or 10k course, with the event featuring chip timing, finisher medals, and technical event shirts. The course includes trail segments with some roots and hills, and wate..

The Rick O'Donnell Memorial 5 Mile Trail Run and Ultra Challenge is an annual event held in Mount Airy, Maryland, organized by the Frederick Steeplechasers Running Club. Taking place on October 12, 2025, it features three challenging race options: a 5-mile trail run, a 4-hour challenge, and an 8-hou..

The Delaware Trail Fest, held at Lums Pond State Park in Bear, Delaware, is a trail running event celebrating the state'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 cours..

The Fall Backyard Burn Trail Run at Lake Fairfax Park in Reston, VA, offers runners a scenic and engaging trail experience with distances of 5.1 miles (one lap) or 10 miles (two laps). The course features mostly smooth singletrack with some short technical sections involving rocks and roots, minimal..

The Patapsco Valley 50K is an annual trail running event held at Patapsco Valley State Park near Baltimore, Maryland, with race headquarters at CCBC-Catonsville. The event features two main distances: a 50K and a 25K, both available as in-person or virtual races. Runners enjoy a scenic, historic, an..

The Halloween Horror 10k is a trail running event held at Conway Robinson State Forest in Gainesville, Virginia. The course features a loop through forest trails with some technical terrain and minor hills, with the 10k consisting of two laps of the 5k route. The event welcomes both runners and walk..

November 2025

The Fall Backyard Burn Trail Run at Riverbend Park in Great Falls, VA, is a scenic trail running event held on November 2, 2025. Participants can choose between 5-mile (one lap) and 10-mile (two laps) courses featuring beautiful riverside singletrack trails with a few short hills and stunning views..