Find the top rated walking trails in Shippensburg, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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It’s definitely a rail-trail: pretty straight and flat. This trail reminded me of the Torrey C Brown trail in northern MD. It was a little rough, but certainly not unridable or even particularly unpleasant on my 700C hybrid bike.
I just finished a two-day solo tour (Cumberland to Williamsport, Williamsport to DC) and had an incredible experience despite the rain and the tough going over a few stretches. I hear a lot of criticism about the C & O, particularly when compared to the GAP (which I have also done). I appreciate the contrast and hope that the C&O retains its historic character as a more rugged towpath (not a rail trail). That said, the conditions on the east side of Paw Paw and from White’s Ferry to DC were challenging (again, I like the changing surfaces). Highlights: wilderness character, Paw Paw Tunnel, sycamores between Harper’s Ferry and Antietam, Great Falls, Monocacy, Point of Rocks station and the towns.
Billie and I rode the trail (some of it) on June 3rd for the first time. Headed South we got to the blockades at main St. I heard commotion under the overpass. I went and talked to the workers. They told me to ride through as the trail is open, but the horses were not removed but will be shortly. We are riding another section today. This by far, is one of the most interesting and beautiful trails we have been on.
The trail is easier to follow than I expected due to the “bike route” signs throughout. It’s in good shape. Multiple times it shares the road for miles at a time, but these roads had very little traffic.
Although not totally connected, we found this trail to be delightful. It takes you through some safe, side streets to a fairly flat, forested path. The woodsy part is dirt/gravel and can be a bit challenging, as you need to be aware of the twigs, uneven surfaces,and wildlife. But hey...isn't this why we ride?
I live in Northeast Lancaster county and have ridden most trails in this area. The Lancaster part of this trail was repaired with unridable large gravel. The last time I rode it, we stopped and turned around as we worried about the impact on our bikes. It’s a jarring unstable trail surface. We now only ride the Lebanon county part of this trail … which is beautiful, picturesque, shaded, uncrowded, and well maintained.
Well maintained and shady in the summer. Pastoral views
Well maintained and shady in the summer. Pastoral views
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.
We have ridden this trail several times. This is the last. Since the last time we rode here, they have topped the trail with large stone. It is so hard to navigate, it feels dangerous. We had to concentrate on the trail, rather than enjoy the surroundings. Used to be a lovely ride.
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