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.
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.
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.
The Brandywine is the perfect city park. It connects most every neighborhood along the Brandywine river. Plenty of space for joggers, kids, dogs and folks who use walking aids. Scenic, clean and minimal noise pollution.
I biked the BWI Trail today with my son. We had a fantastic time. We covered 12.4 miles, and the trail was smooth, well-maintained, and easy to navigate. It loops around the airport, but you’d be surprised scenic it feels, with stretches of greenery, wooded areas, and even a few nice rest stops. Great for casual riders and pros alike. We’ll definitely be back for another ride.
The map shows the trail stopping at Main Street in Bel Air. Another mile has been added to that. It’s been there a couple of years and now they are working on a new section. When done this will connect the two sections that are existing. While this is the closest trail to me I seldom ride it because of two things. 1 is it does not really follow the old rail bed the whole time. Because of this it has some major hills. 2 is that it is to crowded for me. All personal opinions.
An amazing free resource for the lower eastern shore. Flat sand trail mostly covered with pine needles. I would not recommend this trail if your tires are less than 50mm (2 inch) wide. Minimal but effective main trail markings. Multiple unmarked side trails. Adequate parking. Pack a lunch and make a day of it. This is a state forest not a park, there are port-a-john's near the parking area.
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