Explore the best rated trails in Greensboro, MD, whether you're looking for an easy walking trail or a bike trail like the Ben Cardin C&D Canal Recreational Trail and Maurice River Bikeway Trail . With more than 63 trails covering 255 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 kept hearing how beautiful this "trail" was. Most of the "trail" was city streets even before you get in to Baltimore. It was also poorly marked. Keep a GPS handy, or just give up on the trail and ride through whatever Baltimore streets you feel like riding.
It does take you past the Baltimore Zoo which was nice. It also takes you right in to Inner Harbor which is also a good place to hang out for a bit.
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.
Not much to it. Just paved and easy. The trains do get loud so maybe not the best for small children.
I connected this ride to the Cape May Loop and it was a fantastic way to get in some good miles in the morning hours. I rented a Trek Domane from the Surf & Buggy Center. The bike was great and they delivered it and picked it up. If you are looking to get some good training in during your stay this is the way to do it.
Highly enjoyed the paved path, the wildlife sanctuary you ride through. Nice to stop for dinner on the Waterfront in Wilmington. Very nice path
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.
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