Find the top rated cross country skiing trails in Waynesboro, 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.
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Please make sure you have bike lights, flashlights etc… those tunnels are dark!!
I just rode the trail 11 Oct 2025- shortly after the new Sideling Hill Trailhead grand opening a couple of weeks ago. I utilized the PA Turnpike to drive up from Harrisburg area- very easy and trouble free- just know that afterward you have to drive another 10 miles UP the turnpike to turn around and head back to Harrisburg....ugh 20 additional miles, even though both East and West bound have access to the Sideling Hill Rest Stop. Trail Head had really nice bike servicing equipment and picnic tables- Lots of food options at Rest stop- everything you need after 20 mile ride- Burgers and Pizza!! Leaving the rest stop- you ride a service road that is open to bikers (Mountain House Road). You then come to a 4 way stop- Make a left on North Hess Road- you will see a old farm/log cabin house on your right (see my pictures)- go straight this road will turn in to Pump Station Road- ride for about 1/4 of a mile do not turn on the first unmarked road on your right- go to the second road on your right just after the first one- look for a mail box- there is a home that shares the access- ride past home and you will be at the TOPP Trail- you will see cement road barriers on your left- this is the entrance to the trail- Enjoy your ride for the next 8 miles or so. The first tunnel you reach is about 1.5 miles up- This one is long and dark maybe a mile long. The second one is shorter. The trail is rough in sections due to the blacktop being torn up- if your a Pennsylvanian- this a typical PA road LOL potholes! Beware if you are with children or offend easily- There is a TON of Graffiti and things that will make a sailor blush (I used to be in the Navy). There is some really talented art work along the ride though. I would recommend mountain bikes or gravel bikes- my bike has 45MM tires and I rode with 35 psi which I thought was perfect for the rough areas. This trail was "Creepy Cool" and a perfect ride for a fall day and Halloween around the corner!
This is probably the most I could handle on a bike ride. We rode the GAP and C&O back to back like many do in 8 days. It was great fun but the C&O is noticeably rougher, fewer port-a-Johns and very scarce potable water sources. On our 7th day from Williamsport to Brunswick we ran out of water midway and rode the remaining 25 miles without water. Fortunately the shade offered by the beautiful canopy of trees made it bearable. We made sure to load up on extra water on our final day. The mix of loose sand that caught us by surprise & the larger stones on the trail made for a more challenging ride than expected. On the one rainy day we had from Cumberland to Little Orleans, some of the puddles we encountered offered a new sense of “oh dear” as we didn’t know how deep the hole we were riding thru when there was no room to go around the puddle.
Perfect day for a ride and on the first day of Fall. Trail and views were breathtaking!
Biked from Hancock to Little Orleans and return on August 30, 2025. Distance: 34.5 miles. Stopped for lunch at Bill's Place in Little Orleans and got good food and friendly service. The paved portion of the trail is in excellent condition -- thanks to the Maryland Park Service for recently repaving the trail. The only negative is the 3-mile detour on the C & O Canal towpath around the abandoned Indigo tunnel. The towpath detour is unpaved and has a rougher surface than the trail. The nearly one-mile long tunnel was closed in 2010 to protect a handful of bats allegedly living inside. The tunnel is an engineering marvel that should be seen and experienced by humans. Opening it to trail users would help the economically depressed Western Maryland area. For example, the equally-long Blue Ridge Tunnel in Afton, Virginia, draws about 50,000 visitors annually since it was reopened in 2020.
We camped at Indian Rock Campground right along this trail. It was a lovely comfortable ride with our mountain bikes. The Howard Tunnel was neat too. We highly recommend this trail.
Beautiful quiet rail trail that we have added to our favorites list.
We Loved this trail. We got on at the Brillhart Road Parking lot went down the trail through the Howard tunnel, all the way down to the Hanover Junction. It was pretty much all in the shade. There were sections with very low grade ups and downs but the grade was so low you couldn’t see the hills visually, you just felt the difference in your legs. There was also minimal street crossings and they were all super small back roads with minimal traffic, which was great for my kids.
there are some really old bridges that go over the C&O. the highlight is the paw paw tunnel. better to walk through it. once you hit little orleans, i suggest going on the western maryland trail. it is fully paved and nice.
hancock is a great town
I love going on this trail when riding my bike to work. It's so nice to ride without cars being beside you. When going out early you can see all kinds of wildlife out.
The trail is in good shape. They have completed an extra few miles at the end that are fully paved. There are many benches to sit and multiple entry points. There is a brief ride on streets. The bathroom works and there a a few port o potties. I liked it
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