Explore the best rated trails in Ridgely, MD, whether you're looking for an easy walking trail or a bike trail like the Ben Cardin C&D Canal Recreational Trail and Cross Island Trail . With more than 54 trails covering 220 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 started riding this trail in 2018 and rode it 3-5 times a summer. It was a great trail that allowed you to get 12 miles in before riding the Cross Island Trail just 3 miles away. The tree roots have been bulging the asphalt for the past 7 years and now it is so bad I don't know if I will ride it again. For the first 1-2 miles from the start of either end the roots have the asphalt bulged up over two inches. Even riding with a suspension seat post the trail jars your spine unless you are standing on the foot pegs. Since the roots are so numerous this means you would be on the pegs 50 percent of the time. With the financial state that Maryland is in I doubt this trail will be repaired any time in the foreseeable future.
I was looking for a trail run, and this was essentially like running on sand. Wasn’t a big fan. The other trails in the park are better.
Stretching for more than 2 miles across Chestertown on MD's Eastern Shore, the Wayne Gilchrest Trail is a scenic greenway that has the potential to connect to more communities.
Like many town-based trails, the paved, multi-use path allows residents to walk or bike between communities with minimal street crossings. It links Washington College with the north and south sides of town and the southern terminus along Cross Street is just a short distance from the waterfront at Wilmer Park as well as the historic downtown. Also notable is a spur of the trail that branches from the main path on the grounds of an office building and parallels High Street, connecting to the northwest side of town and ending at the former Radcliffe Mill, which has been restored and now houses a restaurant and microbrewery.
The trail also serves as an outdoor museum of sorts and features several sculptures and murals along the route, while the old train station, vintage passenger coaches and caboose at the southern end off Cross Street are a testimony to the rail line that used to run here.
Last, but not least, the lush vegetation that lines most of the trail's route provides a serene atmosphere and is a great place to observe local wildlife. The section from Mill Street south to Cross Street forms a greenbelt between residential communities and the Lawrence Preserve nature area, whose wetlands can be further explored through a network of paths extending from the trail. The ravine that forms the trail's route through the Washington College campus and the embankment on the portion north of Morgnec Road are also notable for their beauty and serenity.
My only caveats with this premier small town trail are the busy crossings on Morgnec Road and High Street, though flashing signal lights that warn motorists when trail users are crossing reduce the danger to a degree and the lack of any direct connection to Washington College. It would also be nice if a separate connector path or sidewalk could be built along Morgnec Road that would link the NW Spur of the trail with the main route on the north side of town so that trail users don't have to use the shoulder of that busy road.
Although currently confined to Chestertown, local officials are exploring plans to extend the Wayne Gilchrest Trail further north along the old RR towards Worton, forming part of a bigger network of greenways on the Eastern Shore.
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!
We loved this trail. We went from Cape Henlopen to Rehoboth , then took this trail back to the campground. It was beautiful!!
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.
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.
It’s in great shape compared to some of the city streets, and is somewhat well-marked. I used the map on the TrailLink app to make sure I didn’t make a wrong turn, and would recommend the same to other riders. Sometimes you have to share a sidewalk or street, but when you do they’ve been widened for it. North of Falls Road, there are several sets of switchbacks and several hills.
I often had to slow down for pedestrians on a weekend in February. Has some brief but aggressive climbs. Excited for the final piece to open soon.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
