Find the top rated horseback riding trails in Middletown, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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Rode most of the trail yesterday starting in Railroad, PA on the Heritage Trail and turned around at the old train station in Monkton, MD. Temperature was in the mid-80s, and humidity was high. Because most of the trail was shaded, it was still a great ride. Definitely not a trail for narrow road tires, but still an excellent surface of crushed stone and hard packed dirt. Plenty of restrooms and stops available. Slightly downhill starting in New Freedom, PA into MD for about 6-7 miles and then a typical rail trail of mostly flat and straight sections. Great scenery of wooded areas. Highly recommend for a relaxing ride in the woods.
Definitely an adventure on a bike. Some parts are smooth; others are pretty rugged. Just be prepared for some rocks. 10mph feels like flying.
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
Pedaled from Kernsville Dam to just south of Auburn, 6 miles one way. Really nice section of trail. The new bridge over the river between Stony Creek trailhead and Auburn is open. Didn’t have time to pedal all the way to Auburn, had to turn back.
Highly enjoyed the paved path, the wildlife sanctuary you ride through. Nice to stop for dinner on the Waterfront in Wilmington. Very nice path
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