Trail Running calendar near Anne Arundel County 2026-2027

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

A cross country 5k and 10k at 868 Estate Vineyards with chip timing, a virtual option, race awards, and a postrace glass of wine for participants.

Experience the twisty single track and scenic farm fields of Germantown at this trail running event. Participants can choose between two distances while supporting local non profits in Montgomery County.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in Georgetown for the Christmas in July 5k and Half. Participants can choose between two race distances or join virtually from any location.

Run a technical 8K trail through vineyards and along the river at Bohemia Manor Farm. The chip timed event includes a tech shirt and wine glass. Celebrate after with a waterfront party featuring live music and food.

Explore the wooded trails of Little Bennett Regional Park in this trail run. Choose between a beginner-friendly 5K+ or a 10K course featuring single-track paths, hills, and streams. The event includes race swag, post-race food, and a free k..

The MD Heat Trail Race on August 15, 2026, offers 50K and 25K trails with river crossings and valley views. Finish with a celebration featuring craft beer and BBQ.

Experience the MCRRC Groovin Woodstock 7K XC at the Woodstock Equestrian Center in Maryland. This low key cross country race offers a scenic 7 km route for club members and non members alike.

Run on the flat, scenic dirt trails of Leopold's Preserve in this 5k and 10k event. Participants receive a medal, shirt, and chip timing, with points counting towards several annual series. A virtual race option is also available.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

The Inferno 10k is a forest trail race on a looping course behind Dirt Farm Brewing in Bluemont. Runners tackle a route with roots, rocks, and elevation changes. Finishers earn a medal, a tech shirt, and a post race beer.

The Pemberton 24 is a unique 24-hour challenge in Maryland's Pemberton Park. Runners and teams attempt to complete as many hourly 5 km loops as possible, earning points for each one. It's a test of endurance with a supportive camp atmospher..

Trails 4 Tails offers a 40-mile ultra, a 40-mile team relay, and a 25K on a scenic multi-loop course through Codorus State Park. The trail route features varied terrain and changes direction each year. All races finish at a stocked pavilion..

Event Information The River's Edge Endurance Challenge takes place in Brunswick, Maryland. The event is the 8th annual edition and offers three different race distances. Distances 5K (3.1 miles) 3 Hour Endurance Race 6 Hour Endurance Chall..

Experience the oldest trail race in the county with 10 miles of rocky terrain, steep hills, and river views. This historic event offers a technical point to point course through the scenic landscapes of Eastern Pennsylvania.

Join a community 5K run and walk through the scenic trails of Agricultural History Farm Park. Enjoy a morning of music and fitness with events for all ages and awards for top finishers.

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.

Experience a dog friendly trail race through the varied terrain of Caledon State Park. Run a 10K or 1 mile course with your leashed companion to support local natural resources and educational programming.

Experience a technical trail race through the historic Glenroy Preserve. Choose between five mile, 25K, and 50K loops featuring creek crossings, rolling hills, and post race celebrations.

Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.