Explore summer 2014 - view hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

summer 2014 Map

Great hike, the “caves” were more like GIANT boulders and really fun to explore around. It was pretty wet in a lot of places so I would recommend water resistant hiking boots. Our dog loved it too!

Beautiful hike! The view is super nice on top (and can be a bit crowded). I would recommend to take Paradise lane trail to get up there as you will encounter a "wall" of rock to get to the view point. It will be easier on your body to climb this wall rather than go down on it. Can be done within 2-3h.

5 days ago

a really nice hike with a nice variety of terrain and great views

Nice views from tower and nearby places. One of the best places in this area. Very busy during weekends, especially packed on parking lots.

10 days ago

Exciting and different I really enjoyed this trail. Avg difficulty. Some rock scrambles.

11 days ago

I’ve hiked up to Bear Mountain many times but I normally take an in and out (Undermountain trail to AT to Bear Mountain then back down). Today we did this loop- Undermountain trail to Pleasant Lane to AT and back to Undermountain. Undoubtedly the loop was more fun. Right before the Bear Mountain summit there’s some great rock scrambling. If you’re going to do the loop I recommend going counter clock wise (up Pleasant Lane and down Undermountain) to avoid having to transverse down the rock scramble. The rocks are pretty wet and slippery but they weren’t difficult to climb, I would just prefer to climb up them rather than down. We’ve also had a lot of rain lately so it was a pretty wet trek overall. Views are amazing and well worth the hike.

12 days ago

Hiked this trail many times since my teenage years and always enjoy the view from the top at 'Black Rock' esp this time of year.
Trail is moderate and can be challenging for anyone not used to steep climbs but def manageable just take your time, using a hiking pole/stick can be helpful. Total time to top from parking area inside park is 30 minutes or less.

21 days ago

Quiet trail. Would do again

I really enjoyed the hike, will definitely be back. Didn't find the caves but did make it to the cliffs.

23 days ago

Really fun hike.

Well marked and not very challenging. If you have bad knees, hike the loop counterclockwise (go up Paradise and come down Undermountain)...you’ll avoid a short, but challenging descent near the summit. Nice views at the top.

27 days ago

great view on the top.nice hike

29 days ago

I love this trail. I prefer to take the Paradise trial up since there is a steep rocky section and I find it easier climbing up the rocks if the trail is wet. Due to heavy rainfall many sections of the trial were wet and muddy.

1 month ago

Did this on Sunday, it was a gorgeous day! I brought my 11w old puppy with me and a friend. We started at about 1030 and ended around 3pm. Having the puppy made things a little slower but overall really enjoyed the hike! Tried to take the route preferred by commenters but I believe we ended up taking the opposite direction which means we were butt scooting down some of the rocks because it was so steep! Still a lot of fun though! Made me question how some of the other folks I saw pass us were making it up that way though.
It was pretty trafficked though.

1 month ago

Great hike! Especially during fall in CT. My husband and I hiked yesterday. We took the advice of others here and took a right at the fork to paradise lane trail to do a counterclockwise loop. The trail is easy to follow and accurately rated as medium. The rock ledges before hitting the peak were the hardest part. The view at the top was lovely, and going counterclockwise allowed us to enjoy the views on the way down as well. I tracked 6.35 miles and we finished right around 3 hours including our lunch stop at the peak.

1 month ago

Don’t go on a weekend if you don’t like seeing other people on the trail.

1 month ago

Hi ya'll I did this hike yesterday. I think it is accurately labeled moderate, although I'd imagine if you are a seasoned hiker on trails with incline it might seem easier. The most challenging parts of the hike for me, were the first 20 minutes before it splits, and the half mile up the rock scramble before the summit. However, there was plenty of flatter sections to allow you to catch your breath.
I took the suggestion of doing the loop counterclockwise, and am glad I did. Personally I don't think I would have liked climbing down the rock slabs. They were pretty damp and slippery. Also, because I did it counterclockwise I was able to continue looking out on the view as I made my way down. This hike took me about 3 hours 40 minutes. I definitely took my time going up. Made a few breaks, but was able to come down at a pretty good slip. Enjoy!

Great hike

Great hike. Bummed we apparently missed the trail that breaks off for the bridge, but overall very good hike.

1 month ago

I’m not a seasoned hiker and this trail was really easy. It was a bit slippery today and I was lucky to make it before it got too busy. If you’re looking for a lighter traveled path, this one is not for you. Go early to avoid the crowds.

Great hike to do with kids, some rock scramble, beautiful views and not too long. When the trail changes from blue markers to red they are a bit sparse (perhaps some trees that had markers on them had fallen down) so we missed a red turn and had to double back. (we took the blue trail up and the red trail down.)

1 month ago

Great hike.

definitely worth it nice up and down few wet spots but enough roots and rocks to keep your feet dry caves are pretty awesome and also saw a gray fox on the way back from the caves near the top

oh yeah, I also saw a gray fox on the way back from the caves

definitely worth it, few spots with mud and puddles but enough roots and rocks to keep your feet dry, caves are pretty awesome, highly recommended

Nice hike with area's to rock climb and a great view at the top.

A short trail but worth it. Amazing views along the cliff and the tower at the end. Worth it to go when the tower is open and you can go up to the top and get some amazing views. Underline amazing.

A good trail. I recommend it. Some up and downs but nothing too crazy. It rained the day before I went and I saw all kinds of mushrooms on the trail.

trail running
1 month ago

I liked the trail a lot for it's distance. Clocked 4.5 miles plus 1,400' of ascent down & back. Bouldered at the caves some. Man are there some hard problems over there!

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