Find the top rated cross country skiing trails in Hagerstown, 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!
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 started at Lake Needwood which had great parking. The trail is not well maintained. It is bumpy most of the way south. It looks like there has been some attempt to patch the asphalt but the transitions were not smoothed out so many jarring bumps. Also tree roots have pushed up the trail which is not unusual but given all the other bumps it was annoying. Also be aware that from Lake Needwood - it is downhill so if you are returning to the same spot, you will have an uphill climb which is not too bad.
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
I try to bike here every year and look forward to the added 2 miles or so connecting Red Cut to Saxton. Riders should note it's not the smoothest trail, the section north of Tatesville is 4 miles of slight uphill southbound that taxes in the summer heat, and if you like human interaction you will be disappointed. Also, when passing though Hopewell, remember this, I HOPE I can find the trail, WELL, I guess I'll just ride until I find it. The southern end is indeed down a nondescript gravel road off Rt 915 leading to Coopers Sawmill Rec area and a private seasonal camp. The northern end continues from Broad St, and in any event the town is so tiny you won't get completely lost. So enjoy the solitude this hidden trail can provide, and if you like busy paved trails, then Pittsburgh has much to offer you.
My wife and I rode from Newville to Shippensburg today. It was @ a 10 mile ride to the Shippensburg Trailhead. We continued for 2 more blocks on Earl St to King St. On the corner of Earl & King is the King St Diner, good and good prices.
The western end is paved and is a nice as any rail trail anywhere. Just short. The eastern end has a boardwalk section and then drops you on a gravel section. The gravel is a little big for my liking. I was on a road bike riding 30s but did fine. This section goes through a cut in the mountain made to get the railroad a level grade.
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