Explore the most popular dogs on leash trails near Wintergreen with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Be warned: If you zoom in closely, you will find several portions of this "loop" that look as if someone handed a crayon to a four-year-old. These are points where the author of this trail got lost, and guess what? That gets to be a part of your experience too! That's because this isn't actually a designated trail at all. Rather, it is a patchwork of various smaller trails that someone tried to string together with only marginal success. Even with phone in hand, when you come to a fork in the path, it can be very difficult to discern which way you are supposed to go next. So be wary!

In addition, several portions of the trail are either not well-maintained, or so sparsely trafficked that you can expect to be walking through almost knee-high brush.

Unfortunately, all of this takes away from what would otherwise be a very fun hike that takes you past multiple lookouts with views that do not disappoint, numerous rock formations, and even a handful of stream crossings.

So, if you want to enjoy this hike I would seriously recommend stopping at the visitors center and picking up a map of the local trail system and only using this as a loose template!

I really enjoyed this hike yesterday (a Fri.) The ascent (counter-clockwise) to the peak is a workout, but definitely doable with some breaks. You do have to deal with a very rocky trail near the top, not a scramble, but probably challenging if not in decent shape. A bonus about this area is that another 3.2 loop (Jack Albright Trail) trailhead is accessible from the Humpback Rock trailhead parking lot. And you can add on to either as the AT is connected to both. The JAT loop was a perfect 2nd hike after doing the HR loop, basically a walk in the woods. Ranger mentioned that he estimated about 6 bears were active in the vicinity. Only saw many people on the up and back to the HR summit.

Very enjoyable hike. Just happened to be scarce traffic on Humpback.

This is a gorgeous trail and a fun way to get to the humpback rocks. Although this loop is longer (3 miles up instead of 1 mile up), it’s less strenuous than the steep, short, populated way to get up to the rocks. The total trail is 4.2 miles. This trail is mostly rock and can be a little wet so make sure you have proper shoes! This trail takes you through a beautiful forest path that zig zags up to the top and then you’ll follow the shorter path down (1 mile down) back to the parking lot. we went after a rainstorm and it was gorgeous being up there with the clouds! As an experienced hiker with a stop at the top for the view it took my 4 hours. Definitely a great hike!

The biggest thing to note on this is the one way part of the loop to and from the shelter. Once at the shelter it was not clear to us to retrace our steps, so we ended up another mile out at a family cemetery (certainly worth visiting) but that put us off our timing and we lost out on completing the loop. So remember when you leave the loop for the shelter (a good place for lunch) that you will retrace your steps to get back to the loop to continue.

I took my mother on this hike for Mother’s Day. It was more technical in spots than I was expecting but definitively manageable. The views were beautiful. We hiked to the second overlook for a total of 2.7 miles.

Not a easy hike, it is steep! Very very steep!

Great loop trail. After coming off Hump back rocks ( incredible views), going clockwise, take AT north...I don't know why we got confused.

Great hike close to wintergreen. When parking, be sure to use the trail entrance on the other side of the road. View point is .5 miles in. We did the full 2.5 but didn’t see another view point after the initial one. Would do it again!

Somewhat difficult to run, but a very nice trail. Missed the turn to Glass Hollow Overlook, so be on the look for the turn. Going all the way to the shelter is really nice and well worth it.
I missed having a detailed description of the trail on AllTrails, but I found one online here - https://www.hikingupward.com/GWNF/DobieMountain/

This was ok, but I expected more views. It was some good exercise though

Definitely not what I expected when it said moderate hike. If you’re not in the best of shape it can be exhausting going up. But the views are absolutely phenomenal. It’s a great couple hour hike.

Fun hike. Not crowded. Everyone else at site was walking humpback. Will do again. My dog loved it! :)

I’ve always gone straight up to the top of humpback but this is a great alternative if your just taking your time to get to the top. I finished the 4.1 miles I recorded in just under 2 hours and enjoyed the empty trails.

This is not an easy hike, moderate to difficult is more realistic.

We hiked clockwise and for the first 4 miles or so it was fine. Lots and rocks and definitely tough footing but doable. Then we had to cross wintergreen ski slopes...definitely would check what their season is if doing this hike in the winter. We had to hike across a snowy slope. It was cool, but luckily the season had not started yet. About a mile after wintergreen, the trail became extremely difficult to follow. Lots of different trails intersecting, downed trees and just a general lack of directions. We had GPS but it was tough to figure out where to go. We ended up turning around and hiking back the way we came, so I don’t know anything about the hike past about 5 miles in. If someone else has hiked this, please post your review...don’t think I’ll be hiking this one again due to lack of directions. I will say, the beginning of the hike was beautiful with the waterfall and dramatic rock features.

This was a trail and view I was proud to have all to myself on an early Monday morning. This is an area well known for herds of people pollution, this is why I was amazed to have it all to myself! I tracked 4.4 miles around the Loop Trail using my GPS & Fitbit. I did the counterclockwise route. You can tell by the wore out areas on the amount of people that use this trail. The part of the trail to the A.T. are not used as much and is a very enjoyable route back to the parking area. If you want great pictures without people pollution go on a weekday and go early! I returned to the parking lot to see only one other car and another pulling in as I was stowing my gear!

We hiked it in November around Thanksgiving. The leaves had pretty much all fallen, which made the footing slippy and tough to read in a few spots, but nothing difficult. Beautiful views and not at all crowded.

The hike was nice. We (seemingly, at least) went the reverse of most people and did the switchbacks first, then came down after the rocks, which I actually think was nicer.

My family hiked this route without any issues. I had with me two children ages 6 and 7, and they handled it very well. I would suggest bringing some food and water, as it is a long trip with children. You climb up to the rocks from the parking lot following the .8 of a mile trail. From there you will head back a few hundred feet to a sign post which directs you to the A.T. Follow that up until you come to a intersection with the A.T. sign. From there you will just follow the A.T. north down the mountain until you meet the trail back to the parking lot. The trail was beautiful in October.

Also known as the Jack Albright Loop, we started at the Humpback Rocks parking area, and after climbing up to the rocks, took the AT down to Glass Hollow overlook for a short snack and a nice view, then continued on the AT to the left turn on the Jack Albright trail over Dobie Mountain, which is wooded with no exposures. Nice hike and discovered the plane crash from the 1960s - you can't miss the mangled sheet aluminum cabin and motor housing. Several folks were out enjoying the great weather.

10 months ago

I started counter clockwise and was fairly easy at first, but after a few miles became more difficult. There was definitely a lot of steep inclines and declines. I wasn't expecting to see houses in the start and end of the trail, but the trail quickly became pretty remote. Probably the hardest one day hike I have done anywhere around this area. Some great views and nice waterfalls.

Tried to follow this trail in reverse hoping not to have the problems of other reviewers with trail ID. Followed the service road from the picnic lot for about .4 miles which quickly became a single track and then finally obscured by growth. Had to bail out onto the AT about .75 mi into the hike to continue. Made it up to the overlook which was pretty special with great views of Wintergreen. There is a connection from the picnic parking lot to the AT which I recommend as an out and back. The other nearby viewpoint on the AT directly south of the picnic lot is overgrown and isn't much of a viewpoint anymore.

The trail is in pretty good condition, but some sections are treacherous. This trail isn't for you if you hike for scenic views, as there are only a couple and you're in the woods the entire time. "Hard" is an understatement for this trail's difficulty. Overall, it's a good, challenging trail.

Ran it with a dog... Beautiful and if you do the glass overlook it's 6.2 miles. Would not rate "easy" for trail running! Lol

Great highly with fantastic views along the trail leading to the best views at Humpback Rock. Trail is clearly marked with blazes every 50-100 feet. We could not find the loop back. Using GPS we bushwhacked where the trail should have been but no luck. We returned the same way we came. Most of this hike is on the Appalachian Trail.

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