Find the top rated horseback riding trails in Cumberland, 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.
Bike touring across tha US and I’m currently set in my hammock about 10 mils outside of frostbite head West! Gotta say that MD & PA has out done themselves on tha GAP! Wish other places “you kno who you are WV, yea you! Anyway, I love its backcountry vibe and tha fact that it’s well maintained! Hope tha rail to trail route gets done sooner rather than later and is maintained this well instead of corrupt politicians pocketing tha money! You kno who you are, you! Anyway, to tha hiker and biker trash out there, one love!
Highly recommend this beautiful and well kept trail. Beautiful to ride along the trees and over the 2 epic ohiopyle bridges.
Today we rode from Warrior’s Path State Park to Hopewell and back. We loved the recently opened section from Warrior’s Path SP to Riddlesburg. The rest is a little bumpy in places. If you continue south of Hopewell, you must ride on a relatively rough road until you re-enter the trail. From there you will enjoy the scenery till you reach the bridge, after which the trail moves away from the river, becoming less scenic. The trail currently terminates in Tatesville.
Tunnel is closed. I ventured over the top and it's tough
Just got done this trail 10/9. Gap trail is a wonderful easy ride. Places we stayed were awesome! Bright Morning B&B, Ohiopyle suites. We stayed in the Karly. It was great! Right off the trail!! Coffee shop is great too. They also have a laundromat. We then traveled to Meyersdale where we stayed in the hotel airstream! Gotta stay here! It was great! Know that if you need to take the train back to Pittsburgh like we had too, it can run late. 5hrs for us. We met so many nice people along the way. That’s what I think of when I think of this trail!
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!
I decided to park in Cumberland on my way home from a trip to WV and ride down the C&O towpath to ride this trail.
I was disappointed in the state of the trail. It appears as if no one is maintaining this trail.
The path on the Maryland side is now almost covered with encroaching weeds.
The bridge is in good enough shape to permit you to ride across to West Virginia for the time being but it looks a little iffy. If no one is taking care of this trail the wooden planks may need replacing. At some point it may become a dangerous crossing when these planks start rotting.
The tunnel is blocked off so you can go no further than the WV side of the bridge.
I would recommend that riders skip this trail until such time as it is maintained.
We just finished the GAP trail & C&O towpath 9/20 from Pittsburgh to DC. We took 8 days and our days ranged between 32 miles to 63 miles. Highly recommend this trail. Well maintained, accessible and clean port a John’s, always had plenty of toilet paper and were frequent enough to remove any anxiety about not being able to relieve yourself in privacy. Potable water was available along the trail which we still used a filter just to be safe. Beautiful trail, friendly riders and towns to visit. We rented a full sized SUV in DC and dropped it off at the Budget on Stanwix St just two blocks from fountain starting point. Worked perfectly to get going on our ride without delay.
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!
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