Explore the best rated trails in Leesburg, VA, whether you're looking for an easy walking trail or a bike trail like the Anacostia River Trail and Gerry Connolly Cross County Trail . With more than 108 trails covering 4586 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
I just finished a two-day solo tour (Cumberland to Williamsport, Williamsport to DC) and had an incredible experience despite the rain and the tough going over a few stretches. I hear a lot of criticism about the C & O, particularly when compared to the GAP (which I have also done). I appreciate the contrast and hope that the C&O retains its historic character as a more rugged towpath (not a rail trail). That said, the conditions on the east side of Paw Paw and from White’s Ferry to DC were challenging (again, I like the changing surfaces). Highlights: wilderness character, Paw Paw Tunnel, sycamores between Harper’s Ferry and Antietam, Great Falls, Monocacy, Point of Rocks station and the towns.
My son and I rode the C&O the first week of June '25 as part of a ride from Pittsburgh to Washington DC.
I am going to preface this review making it clear that it was an unusually wet Spring and significant damage has occurred due to flooding. Kudos to the efforts to repair the damage and keep the trail open. There were numerous detours off of the trail but it was open and passable. However, had I not taken this into consideration, and had not just completed the GAP as a comparison, I would have rated the trail 2 stars.
Here are my key issues rated from most, to least, significant:
1) The terminus of the trail in Georgetown is inaccessible due to construction. We rode 334 miles in 5 days to unceremoniously end our accomplishment carrying our bikes up a series of stairs, only to encounter detour signs that literally pointed in all four directions. After a half hour walking through urine-laden alleys searching for mile 0, a bicycle cop told us that we were as close as we could get. Our victory picture was taken next to a detour sign, each of us providing a middle-finger salute.
2) The trail surface through the Paw Paw tunnel can only be described as interconnecting pot holes filled with 6" of water. Had there not been other traffic in the tunnel, it may have been rideable. Just accept that you will get the opportunity to stretch your legs for a half-mile walk in the dark. Your shoes will eventually drain and dry by the time you arrive in DC.
3) For 15-20 miles south of the Paw Paw tunnel the trail is unmaintained. The riding surface is basically sunken truck tire tracks, separated by a hump of uncut weeds. The tracks themselves were devoid of any gravel which ensured that you were riding in either water or mud. The weeds on both sides of the trail had yet to be trimmed and had encroached into the tracks. The good news is that we were concentrating so hard on keeping our bikes upright in the slop, we didn't have time to think about the ticks. Anyone who has hiked the Adirondack high peaks knows exactly what I am describing.
4) Most of the trail repairs have been made with loose, coarse, crushed stone. I was fortunate to be riding a mountain bike with 2" tires at 60psi. My son was riding a gravel bike with 40mm tires which mean he was riding sideways much of the time. He ended up riding a combined total of 400 miles considering the lateral component of his travel.
5) Where washouts had yet to be filled with the previously mentioned stone, you have to cross crevices 6-8 inches deep. Not such a big problem if you were travelling slow enough to identify them before jamming your arms through your shoulders and ramming your saddle through the softer tissues of your rear end.
6) Having camped in Assateague for half my life, I thought that I knew aggressive mosquitoes. However, since the trail is totally devoid of any breeze, the stabbing critters locate you as soon as your bike comes to a halt. The good news is that we saved time taking breaks.
I will be posting a 5-star review for the GAP next. If you average the two scores together, the total trail experience was a 4. That still makes the ride from the 'Burgh to DC worthwhile. Just be prepared for the unexpected challenges.
I just rode 28 miles round trip today (May 30, 2025) on the WB&A Trail and it was great!
Contrary to the narrative in the description, the bridge over the Patuxent River is now open.
Started in Odenton and parked on Railroad Ave just North of the trail entrance and rode all the way to Annapolis Road (Rt 450).
Lots of bikers and pedestrians out on the trail today.
Great day to ride!
The bridge is open and you're able to ride the full length of the trail. Great nature viewing throughout the ride. Surprisingly, over 1000 ft of elevation gain.
Some parts east of Carroll Park were a bit sketchy. That said, I love the variety that this trail brings. Western part is very well-signed and doesn’t even feel like city. Eastern part is a bit more confusing (I definitely recommend having the map open). This was a fun 2 rides.
This experience is based on parking at Mount Vernon and riding the trail for approximately 4 miles in one direction, then returning. The trail is primarily paved, with a scattering of wide wooden bridges to cross. You will ride an asphalt two-laned path through lightly forested areas as well as open areas, so you can enjoy the sun and the breeze coming off the Potomac River. The scenery is spectacular, and gives you the opportunity to forget that you are in Northern Virginia.
However, there are a lot of inclines and descents that some may find challenging. If all else fails, just get off the bike and walk, and pick up riding when the trail flattens out. Part of the route -- not the trail itself -- goes through a short tunnel, so the trail ends at the tunnel entrance, and picks up again once you go through and exit the tunnel. This means while in the tunnel, you are on the road, and not on a bike path. For children bike riders and hikers, extra precaution should be taken at this point. Other than that, absolutely stunning views of Northern Virginia and the Potomac River. Bald Eagles can be seen flying over the water as well. This trail is definitely a do-over!
Rode south from Inner Harbor to MedStar Harbor Hospital, a decidedly mixed experience. The "urban" part is tricky, not well-signed, and lots of crumbly asphalt and broken glass. The spot where the Middle Branch Trail/E Coast Greenway hits Russell St (south of Top Golf, just north of the Wheelabrator) is also a spot for people to gather, didn't feel very safe. (It was neat to see Gwynnda the Good Wheel of the West near there, however.) The "Westport" section of the trail feels very exposed: deserted industrial with occasional cars with opaque windows...once you arrive to the Middle Branch Park, the trail is more park-like but not well-populated even on a beautiful day and the trail is not in great condition. Pretty views of Baltimore from the coast. If you're departing from the inner harbor, would recommend just biking out to Fort McHenry instead - a bit more traffic but feels significantly safer and much nicer.
I rode this for a second time recently. The trail is in great shape. I will they would add the path through the tunnel. Extending the trail over the three bridges would make this the best in the area. Not sure if that is a plan. Hancock is a great town. Very remote in little orleans
I park at Maryland Ave off of MacArthur Blvd and hop on the car-free path here. Lots of lovely scenery and never crowded. Weekends there are a lot of street bikers but the pathway is always easy going. Restrooms across from Old Angler's Inn - good turn around point. Great ride.
This is my favorite paved trail. All the bumps and roots are gone since the repaving project was completed in fall 2024. Hancock is the town at about the middle mileage. The western end is quiet through the woods. There are very few road crossings and it's pretty flat grade. Berkeley Springs WV is only 6 miles south of Hancock MD and that's a cute tourist town to visit. There's also a good bike store in Hancock.
Ok section, kind of dull. Agriculture & cows. Found a bit of shade by a grain elevator for lunch. Several washouts filled with tumbleweeds as you get closer to Lind.
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