Explore the best rated trails in Fairland, MD, whether you're looking for an easy walking trail or a bike trail like the Anacostia River Trail and Meadowlark Connector Trail . With more than 118 trails covering 4679 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.
The trail is 100% paved and takes you along the Anacostia River. I like that this trail has a good mix of city elements and natural beauty. The Kenilworth aquatic gardens are a wonderful stop early in the trail, you get to see a lot of swamp flowers. Later, closer to Dc you are taken up to the Fredrick Douglas memorial bridge. The large white arches of the bridge are breathtaking. There are many places to eat diner once you make it to Dc. I stopped at Gordon Ramseys fish and chips. Great trail!
Starts at a dam and has some hills. It is not bike/stroller friendly. Hiking boots are better. Sneaker can be a challenge especially after rain. Dumps off into a neighborhood and you pick it back up. About a 4 mile loop.
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.
Billie and I rode the trail (some of it) on June 3rd for the first time. Headed South we got to the blockades at main St. I heard commotion under the overpass. I went and talked to the workers. They told me to ride through as the trail is open, but the horses were not removed but will be shortly. We are riding another section today. This by far, is one of the most interesting and beautiful trails we have been on.
Paint Branch Trail is good with one fatal flaw. Just west of Lake Artemesia there is a railroad underpass that develops a large mud pit after rainfall. Most of the time I've used this trail it has not been an issue, but I recently rode it after a rainfall and there was a mud pit approximately 25 feet long, with mud 2-3 inches deep, with no way around. Very unsafe and very irritating.
The trail is paved and easy to ride, and the water fountains that line the trail actually work! Great for beginners and experienced riders. Well-populated but not overcrowded.
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.
My husband and I broke the trail up into 3 segments between May 8th to May 19, 2025 riding our bikes. We started at New Freedom, PA and rode to Walker Road and back. (14.2 miles). The next time we rode from Walker Road to Monkton station and back. (14.2 miles). Then we finished the trail riding from Monkton to Ashland Road and back (14.2 miles). The scenery included beautiful foliage, a winding creek, and various forest creatures. The trail itself is well kept. It is also well traveled with walkers, runners and cyclists.
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