Explore the best rated trails in Chestertown, MD, whether you're looking for an easy walking trail or a bike trail like the Springlawn Trail and Delcastle Recreational Park Walking Trail . With more than 84 trails covering 394 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.
There is no access in Atglen, and no apparent trail. We drove further west to Bart Township along Route 896 parking at the Evergreen Hardware Store. There is a switchback down to the trail. For about two miles in each direction the trail is nice stone dust, but after that, at mile 23.5 turns into the transmission right of way with just a lane, which is okay to ride towards Quarryville. Going east, you can go to about mile marker 26.5 again with a mile or so in stone dust, but getting to Scarborough Twp it is the transmission right of way - just two single lanes, rideable until you get to yellow gates, unpassable unless you walk your bike down and up inclines. Can't say what's from there to AtGlen - it is high grass and TX right of way at best. If you can, drive down to Quarryville - a very nice trail from there west to Turkey Hill.
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.
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.
The overpass at mile marker 11.5 in Seven Valleys over PA Rt 214 is closed and Northbound trail users must descend an embankment next to the Four Springs Winery and ride through town to Church St to pick up the trail again. Southbound riders follow the same detour in reverse.
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.
The trail is incredibly straight, so it can seem boring at times, but that also makes long rides easy since you can just go without having to slow down for roads or anything. Eden and Bart townships have done work on improving their segments, and the whole trail, even where it says “unimproved,” is perfectly rideable until Atglen, where it does deteriorate a bit. Overall great trail.
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.
This trail is straight-up amazing. I have nothing else to say.
I tried to do this trail in segments in January. The snow melts way slower on the trail than in other unplowed places. I also think the grades in the northern parts are tough.
Who ever scheduled work and approved the contactor to repair boardwalk bridge section along Telegraf Road should look for another job. New boards make it less safe than the old ones. A trip hazard and surface that may cause wheeled users to lose control. It is not improved but made less safe of a crossing for bikers, walkers, joggers, strollers, rollerbladers and skateboarders when they cross it. Almost like adding pot holes to asphalt. Just one persons comment.
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