The 7.9-mile one-way Fort Circle Trail is the only singletrack trail in the District on which mountain biking is permitted. There are quite a few street crossings, including some busy ones, but you probably wonít mind the brief rest once you see how many hills this trail has in store. Its main drawback is how overgrown with vegetation it can get. The center section of the trail from Ridge Road south to Good Hope Road is very nicely wooded and hilly singletrack. South of Good Hope Road, the trail becomes extremely overgrown with plants by the time it enters Fort Stanton Park. North of Ridge Road it is overgrown in some places (though still rideable) and very urban in others.
From the parking lot, take the asphalt path downhill (away from Fort Dupont Drive) and take the first right to continue on asphalt across an open grassy area. The trail soon enters the woods and becomes gravel. It will turn to asphalt again shortly before it comes to a T with another path. Turn right at the T to arrive at the intersection of Ridge Rd and Fort Davis Drive. Cross Fort Davis Drive at the intersection, because you pick up the dirt singletrack Fort Circle Trail at the corner, where it enters the woods. Ride through the hills of Fort Dupont Park until you come to a T. Turn right and you will come immediately to another trail junction. You can go either way here. If you go right you will ride along the bottom of a hill. If you go straight, you will go up this very tough hill to a grass clearing, then turn right to re-enter the woods and bomb down the other side of the hill (makes it worth the effort!) to link up with the main trail again. Continue to follow the trail south through the woods with street crossings at Massachusetts Avenue, Fort Davis Drive, Pennsylvania Avenue, and Branch Avenue. After crossing Branch Avenue, ride up Park Drive a short way to where the trail re-enters the woods on the right. This next section is very hilly. When you reach 28th Street, cross and go left a short way until the trail again enters the woods. There are two more street crossings, at Naylor Road and Good Hope Road. Across Good Hope Road the trail crosses several small bridges and a muddy area on its way to Fort Stanton Park. It will likely become too overgrown to continue somewhere in this area, where you must turn around and return all the way to the intersection of Ridge Road and Fort Davis Drive. Cross this intersection to the trail entrance diagonally opposite you and follow the trail until you hit C Street. Cross and continue to a trail junction where you go right and eventually cross East Capitol Street. After crossing, go up a grassy hill, ride the trail down to Flint Place, and continue a short way to Benning Road. Cross and take the concrete path to the left a short way, then right up a hill and follow the loop around through the park until you return to Benning Road. Return a second time to the intersection of Ridge Road and Fort Davis Drive, this time going back down the paved trail to the right through Fort Dupont Park and to the parking lot where you started.