Trail Running calendar near Annapolis 2025-2026

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..

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..

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..

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..

The Kettle Cooker Five & Dime Trail Race, held at Glenroy Preserve in Nottingham, Pennsylvania, offers three trail distances: 5 miles, 10 miles, and 25K. Runners navigate hills, creek crossings, and mixed terrain on well-maintained singletrack and fields, with some sections threading through histori..

The Full Distance 10k is a scenic trail running event held at Locust Shade Park in Triangle, Virginia. The course features a mix of trails and pavement, with about 40% paved and some hills, consisting of four loops for the 10k distance. This chip-timed race welcomes both runners and walkers and is p..

The memorial 5 Mile Trail Run & Ultra Challenge takes place at Milkhouse Brewery at Stillpoint Farm in Mount Airy, Maryland. It offers three ways to test yourself: a 5-mile trail run, a 4-hour challenge, and an 8-hour ultra, all on a hilly, scenic course that features a five-mile loop of farm lanes,..

The Westover 5k & 10k is a flat, scenic race at Bluemont Park in Arlington, Virginia, along the W&OD Trail. The course is an out-and-back, with the 10k running out-and-back twice. The event is part of Bishop’s Events’ Year-Long 5k/10k/Back of the Pack Series and Fall Series.Walkers and strollers are..

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..

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

Patapsco Valley 50K is an annual ultramarathon held near Baltimore, MD, with race headquarters at CCBC-Catonsville. The in-person event offers a 50k and a 25k, plus virtual options, set on a scenic, historic, well-marked trail course through Patapsco Valley State Park. The race features five aid sta..

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..

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

The Fall Backyard Burn Trail Run at Riverbend Park in Great Falls, VA, is a scenic trail running event featuring 5-mile and 10-mile race options. Set adjacent to the Potomac River and near Great Falls National Park, the course offers beautiful riverside singletrack trails with a few short hills and..

The MCRRC Stone Mill 50 Mile Run is a 50-mile trail ultramarathon in Montgomery Village, Maryland, organized by MCRRC. The course uses forested, rolling terrain along the Seneca Greenway and Muddy Branch trails in Montgomery County, primarily on single-track dirt trails with small stream crossings...

EX2 Adventures' Schaeffer Half Marathon and 10K Trail Run takes place at Button Farm Living History Center in Germantown, MD, on Schaeffer Farms’ scenic terrain. The race offers two trail distances: about 6.7 miles for the 10K and roughly 13.3 miles for the half marathon, with elevation gains of aro..

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 Barrel Oak Turkey Trot is a pre-Thanksgiving running event held at Barrel Oak Winery in Delaplane, Virginia. It features two race distances: a 3k and a 6k, with the 6k consisting of two laps around a cross-country course that winds through vineyards, gravel roads, and hilly terrain. The event we..