Find the top rated walking trails in Greencastle, 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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Please update the Hanover Trolley Trail map. The new section is just beautiful!
We went on a Sunday at the end of May. The weather was perfect and the trail was impeccable. We didn’t go the entire way- we went 15 miles up and then turned around so we didn’t see the tunnel. The honeysuckle was in bloom and the entire trail smelled heavenly. We stopped for lunch at Buddy Lou’s - it’s right on the trail and we highly recommend it. We sat outside on the balcony for lunch and could watch the other cyclists and runners on the trail while we ate in the sunshine. The trail is pretty shaded in many spots so even in warm weather you’d have a comfortable ride. I was surprised, considering the perfect weather and what a great trail it is that it wasn’t busier. This is 10 out of 10 for a great trail experience.
Highly recommend this beautiful and well kept trail. Beautiful to ride along the trees and over the 2 epic ohiopyle bridges.
First time my friend and I have trail skated! This was so fun, especially for 2 67 yr. olds!! Saw lots of walkers, bikers, etc., everyone was friendly, beautiful scenery, squirrels and birds everywhere, great place to rollerskate!
My friend and I went for the first time and had a blast.
I did an up and back 35 miles. Great paved trail and. It many people at this end. Looking forward to riding the rest. I hate dc traffic
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.
The Washington & Old Dominion is the best trail hands down. It is also one of the busiest trails that hosts running clubs, cycling clubs, nature walkers, neighborhood walkers, walking and biking commuters and is at its busiest before 7 am in extreme heat.
What makes this 44 mile trail so unique is the amenities that sit along side of it making it the best trail to plan an activity on with family and friends. Just pick a city that you want to visit and you can find convenience stores adjacent to the trail within walking distance as well as myriad of restaurants for all ages, ice cream parlors, grooming services, bike shops and over the past few years breweries have been added to the scenery right on the trail.
The location is prime to the cities of Northern Virginia with access to getting into Washington DC to see the monuments and Hains Point. Nothing beats the W&OD Trail!
Level, thin tiny crush stone on packed earth trail. Rolls easily, just a step below paved. From small old town of Newville through woods and farmland 10 mile ride to small university town of Shippensburg, with a couple small villages on the way. Horse path is next to bike/pedestrian path. You may see horses and riders on path. You will see farms, barns, cows, sheep, horses, cats, birds, assorted other animals, louse distant mountains. You will smell manure. It is not 15.8 miles. It is 10 miles from park at Newville to Shippensburg. You can add a couple miles by going east from Newville to a dead end. It's a nice ride. In Newville you can park at the park at Cherry & McFarland Streets
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!
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