Find the top rated cross country skiing trails in Middletown, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing 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.
Definitely an adventure on a bike. Some parts are smooth; others are pretty rugged. Just be prepared for some rocks. 10mph feels like flying.
The southern part is paved and easy to follow. The middle section joins with a state park road, and one siding is deceiving. After leaving the state park road, the trail turns to gravel with frequent mud puddles and electrical boxes. Wouldn’t recommend this section to beginners.
Not much to it. Just paved and easy. The trains do get loud so maybe not the best for small children.
I rode today - 7/6/25 - from Oaks about 3/4 of the way to Green Lane Park and back. My first time on this trail in a couple of years. I know there may have been some extra maintenance after storms recently but I found the condition of the trail to be the just about the best that I can ever remember. I ride a mostly road bike which sometimes struggles if the gravel gets too deep or loose in places, but a really smooth and enjoyable ride start to finish today.
The tail is very scenic and fun to ride. But at a few points there are right angle turns to bridges and narrow treat for a shared trail between hiker’s and bike riders.
The Enola Low Grade Trail is a great rail trail for biking and walking. Starting from the Turkey Hill end, the first 6 or so miles are super scenic along the river. Once the trail turns inland it is less scenic but still a very nice ride.
It should be noted that once you reach Hollow Rd east of Quarryville (around mile marker 23 or so), the trail is not particularly bike-friendly and the last mile is so overgrown it's not even really hike-friendly.
The trail is marketed as 29.1 miles, but if you're planning on biking, it is about 23 miles.
“Low Grade” is no exaggeration and this is an excellent trail if you’re looking for a long, flat cruise. As others have commented, the scenic highlights are on the western half of the trail so start at Turkey Hill trailhead if that’s what you’re looking for. Portable toilets at maybe half the trailheads. No easy access to stores/conveniences (except Quarryville) so BYO water and nutrition
Good ride some rocky and sand patches. Few roads to crossover. Plenty of benches to rest
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