Explore the best rated trails in Wise, VA, whether you're looking for an easy walking trail or a bike trail like the Pennington Gap Greenway and Powell River Trail . With more than 17 trails covering 143 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Started at Johnson City trailhead. Trail descends toward Elizabethton resulting a climb back to Johnson City. The trail surface is crushed stone which is not smooth like hard-packed stone dust, so is a rough ride for road bikes.
Well maintained and scenic trail. Loved the painted mileage markers and the school bus. Stopped at the Dairy Bar on the trail for lunch and hung out in the nice trailside gazebos.
We rode the trail from Elizabethton starting in the late morning heading west. Road crossings in Elizabethton were a bit challenging, besides the fact that there are quite a few in a short distance, they come at sharp angles. Have your flashers on and watch the traffic carefully. The remainder of the trail to Johnson City was very nice. I look forward to riding the trail again in the future.
I chose to ride from Swamp Branch to Tip Top Tunnel after reading reviews of not so friendly dogs and less than scenic views at the beginning. I also didnt really want to ride 50 miles. Saw a large flock of turkeys and some deer. I did have a few dogs, but only one chased me until I yelled at him. The path was smooth, with the exception of the sections with lots of walnuts.
I only saw a bathroom at the Jane Beshear trailhead. Clean, but no TP.
Ate a 2nd lunch at the farm at Swamp Branch. Very friendly staff and good food. I said the chicken salad on homemade bread sounded good, but I needed to use their restroom first. I came up to order and she had it ready for me already.
I wish there were more historical markers as I enjoy learning about the history of th area.
There was some trash on the sides of the train, including a broken beer bottle. Someone cleaned the glass up as it wasn't there on my return trip.
The signs posted for distance from Jane Beshear to Tip Top are both incorrect.
This is a very nice trail- the part you can ride as of 9-25-25. The bridge at the 3.5 mile mark is locked off so that is all we could ride from Glade Springs That was quite disappointing. The trail is almost all grass- it was nicely mowed. It had rained for two days prior to our riding so was a little muddy in places but did not detract from the ride. Highly recommend this trail!
On 9/16/25 I was chased twice by a dog at first or second house west of Swamp Branch TH. Fortunately I was able to pedal faster than dog could run. Dangerous for children.
We rode the full length of this trail and really enjoyed it. There is lots of shade through the woods. Signage was great and the views were wonderful. We got off our bikes and spent some time on the suspension bridge, so cool! The path is mostly crushed stone but there is a short stretch next to a hilly road where the rock used was rather large and we decided to just ride the road instead. Overall, a great ride!
I rode the trail out and back from Jenny’s Creek trail head to the dead end at Tip Top Tunnel. Pavement is perfect! Mostly tree canopy! Lots of small road crossing but very little traffic. The huge metal single file guard rails were strange and completely annoying. Strange that there so many - at bridges, road crossings, and even in flat straight sections. Annoying because they were only slightly wider than a road bike bars and you had to slow down and ease through. The facilities were completely toxic - awful. Not cleaned in years. Only 1 water fountain. Please do better.
Did the Mendota to Benhams leg today 13 miles Traveled from Natural Tunnel State Park, and the ride over in the country was great all by itself. Beautiful countryside. The shade and scenery running alongside the creek was absolutely amazing! The signs were informative along the way and those stone benches!! Now that’s a lasting legacy! This route had us going uphill slightly to Benham’s and the ride down was just a coast! Loved it…..I put it up there with the Creeper trail for beauty. You can see all the work that’s been put into it along the way with the erosion controls and borders. Well done VA!
Great trail... I started at Jenny's Creek trailhead, I didn't see another biker on the whole way up to Tippy Top Tunnel.. (it said no trespassing, but I just had to check it out).. it was 25 miles to the tunnel.. I just wished that it went all the way through the tunnel, but was told later by someone that the tunnel had a cave in, so I don't suppose it will ever be a complete connection (sad) that would have been fun to ride through there.. but I started on my way back down and finally ran into another biker, he's the one who told me the history of the tunnel and how he use to ride horses through there.. ran into a group of riders, about 30 of them on the way back down.. I say down because i coasted a lot of the distance in a lot of places.. so it's a steady climb to tippy top, but nothing major..
My only bad experience of the trial.. there's a home a few miles into the ride that has dogs.. and those dogs was on my heals.. they wasn't there on my way back... that was my only bad experience.. maybe I should carry some kind of pepper spray or something to get ride of threats like that..??.. I rode all the way back down to the very end of the trail.. and started heading back to my car.. my other bad experience (my fault) I ride an e-bike and my battery ran out of juice.. that was ok... I was almost to the car anyway.. but it was an awesome ride.. took me 3 hrs to get there.. I live in Ohio.. I spent the night in Paintsville, I visited Jenny Willey Start Park which is that area.. nice park..
May head back down there next year..
Trail was worth the drive. Asphalt paved path with a gentle grade and nice stop in David for a lunch break. Saw several deer and other critters along the trail.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
