Explore the most popular backpacking trails in Connecticut with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

9 days ago

Great hike with some amazing views near and around Cobble Mtn. Started from the lower half and went counter so that I saved the views for the 2nd half of the hike. Perfect hike to do in the fall, the colors are beautiful and pictures cant do it justice. Easy trail to follow and i personally didnt find it extremely hard, did it on a late Saturday Morning after a few showers and had the whole trail to myself until the end where I passed a few people heading up Cobble Mtn in the early PM. By the time I was finishing the weather really cleared up, the sun was shining and the parking lot was starting to get packed, so I expect this hike gets busy when the weather is nice, luckily I dont mind hiking in the rain and the sun was out by the time I started the 2nd half of the hike, so I was able to enjoy Cobble Mtn for myself. This trail has a lot of boulder crossings which were very slippery after the rain and a few of the trails acted as streams, so I highly recommend you have waterproof boots with good traction. Great place to go after this hike is Kent Falls Brewery, its a working farm brewery and they have some great beer on tap made right there for a very reasonable price, plus the workers there are super friendly, youll thank me later!

Love this place! Ha! Do the first uphill twice, (take a right down to the helicopter pad and up again).

trail running
10 days ago

Awesome trail. I came across this trail looking for a place to get a decent long run in. Had just a bit of everything from paved rolling road to soft single track. A few tough climbs but short enough to keep motivated to go on. I would also plan on your feet getting wet. It had rained the day before I arrived but there was still a good amount of creek crossings and marshy areas to navigate. And oh yeah about 3000’ of elevation gain.
I ran the entire out and back and my GPS put me at 26.1 miles. Do pay attention to the yellow Goodwin Trail markers, they are hard to spot in the changing autumn colors. I ran right past a few of them but I can’t complain about it, there were plenty of markers, missing them was my own fault.
Lastly, parts of the single track trail are very hard to navigate due to the amount of leaves that had fallen, the entire forest floor looked like a mix of reds and yellows, which does hide the rocks and roots that I call ankle breakers. Keep your head up (or down) and you’ll be fine.
Overall Richard Goodwin Trail is a must for anyone looking for a good day long adventure. I will certainly be going back.

Happy running-
Ultra Ryan

What an awesome spot we trained here before heading out west to hike Havasu Falls great spot challenging at times with elevation change great scenic overlooks best in the fall in my opinion nice and cool and the foliage was amazing. Highly recommended


Started at Pine Knob loop and Finished at the parking area for St Johns Ledges. Nice hike for a total of 8 miles one way.

Nice hike. Great view. A little rocky. Ran into a bear! Lol

A really nice day on this trail. Easy,not too many others gonna do this again when the foliage is brighter

The Saturday I was there was overcast and dreary with no view of the Berkshires from Rand's view and a slight view from Mount Prospect. On the plus side The Great Falls were RAGIN!! Had a nice picnic at Rand's view will definitely return one day when the weather is nice!!

1 month ago

lovely place. lots of elevation shift with the path crossing water streams several times. lots of muddy and flooded areas and a small section of the closed off for hazards.

Such a beautiful hike. It was the first big hike I've done this year, it had just enough challenge but still for all skill levels. My dog also loved it.

it is well marked. when I went today there was quite a few spots that were flooded over but not super deep. also I didn't see anyone on the trail. I will be going back to this trail for sure

Loved this challenging hike. Almost 8 miles. So glad I went counter clockwise because I got to go up the rock scramble instead of down. Mostly very well marked. A couple times had to refer to app map. Would definitely go again.

I did 2.5 in and out, well worth it,nice views of black pond and beyond,loved the fact that the tops of trail were literally on the egde of the cliffs, loved it, on to the next one✌️

there are some great views on this hike — not just the gorgeous meadow at rand's view, but also the view from mt. prospect and a nice variety of woodlands. i second the suggestion to drive past the marked trailhead and park in the lot by the dam. you can pick up the trail just across the road from there. lots of poison ivy along the trail, so keep your eyes out. but there are also some nice wildflowers blooming right now, especially goldenrod.

Rocks were tough

Love it. The Tower is the best part.

spent time there 40 years ago, thinking of staying a couple nights on the ledges if they still let you. beautiful place to get a little rock climbing experience

2 months ago

hike. It took us about four hours. We started on the eastern side. The trail is marked though at times it was difficult to follow it. The western side has steep sections and a few rocky spots that were challenging. Definitely worth it. We saw just two other people. Visit the town of Kent afterwards.

2 months ago

I found the map here in All Trails a bit confusing, you're probably better off trying to just follow the blue blazes. At one point this map took me through an area that others had clearly walked on (and was just as overgrown as the rest of the marked path), but when I reached the end where it met up with the blue trail again, I noticed it was cordoned off (but not where I entered). Also recommend wearing long pants - you walk through lots of overgrown areas, including lots of thornbushes that can do a number on your ankles. Otherwise a really pretty hike. If you're up to it, take a bag and clean up after the people on dirt bikes, who seem to leave a mess where they stop to take breaks - I picked up a lot of trash.

Excellent route for trail running. Quite steep and strenuous at the beginning (first 1.5km/1mile) then slightly technical coming down the summit of Cobble Hill. After that, the trail becomes top notch for running.
I’ve done it in the winter (rocks get icy and dead leaves are slippery) and summer. Good year round and a great workout.

Rand's View is just incredible, there's nothing in CT like it. Instead of parking where the directions for this takes you, I recommend driving up further until you find a parking lot on the right which is near the dam. It's a 1.8 mile hike from there to the summit of Mt. Prospect. The beginning and end parts of the hike are easy, the middle gets steep. Thankfully it peters out and the last quarter mile or so is pretty flat. The view at the summit is good, though a bit limited with the trees on the side. The hike down to Rand's View was very easy, only about another 15 minutes. I didn't go any further onto Raccoon Hill, so the total hike for me was about 6 miles with roughly 1000 feet of elevation gain. Total hike time for me was 2 hours 47 minutes. It was cloudy when I went but still had a fantastic view. Best in CT!

Great hike. Love the AT, it’s always busy with through hikers and section hikers like myself. I actually did 9.5 miles under 4 hours all the way down to Hoyt Rd. When you come back, i would recommend not taking that right turn along Highway 55, not only it’s dangerous cause of traffic but pointless. There’s two nice views on Herrick trail, Amy’s lookout and Housatonic overlook. I would just stay on the AT and make a sharp left down (going south to Hoyt rd) Herrick trail and catch both views without walking the highway 55. Also, I would just continue on the AT past Hoyt Rd and hike leather hill for 2.2 miles and come back on the AT all the way Bulls Bridge parking lot. You’ll get plenty mileage and steep climbing. Imo, ofc. Happy hiking :)

The NY section is outstanding. In August no readily accessible crossing of water to complete the loop outlined here - had to back track. Wear waterproof hiking boots and tick repellant. Mosquitoes will be an issue for some. CT portion is lovely, but overgrown with grass and weeds - be prepared for scratches and wet clothes. Inconsistently maintained mud crossings that are often in a weird place. Lots of downed trees, but trails are passable. Trail markings are very Connecticut- too few in some spots, but pretty.
Lots of furniture and unusable human structures (cabin-like almost lean-tos that can fit only a small child). Bird boxes, bat boxes along trail. Not a lot of bird calls or small wildlife in evidence, though. Not a wide variety of flowering plants (grass instead). It’s beautiful. Perhaps if more people kick a buck in the donation box at the trail head some trail maintenance can be performed. For instance managing the tulip poplar saplings that will surely choke each other out and create problems for those that survive; re-align and repair the mud crossing; clean-up the liquor bottles on the CT portion; update the trail map. It’s rated as moderate, but it’s more on the easy end of the spectrum. Children can handle it, if they can walk a fair distance, have appropriate footwear and an adult moves the prickers out of the way. If the child is not comfortable outdoors, this walk/hike might not be fun during portions. There are picnic tables randomly placed along the trail.
Dog loved it.
People were arriving as we were leaving on a weekend morning. I bet it gets crowded. Crushed phone battery. Crushed. Bring a portable power supply or turn off. Crushed. A full battery. Having to back track makes the hike little longer.
Pleasant walk. Enjoy.

Really nice trails around a beautiful nature preserve, with an abundance of streams and waterfalls. I walked the entire loop with the exception of the trail up to Hardscrabble Road. It was just too hot and I didn't have time. Trails are generally well-marked. If you visit, you have to cross over into the Michael Ciaiola Conservation Area on the New York side and see the lovely waterfall. When I was there it was flowing to the point where I could not cross to the other side, so I had to retrace my steps back on the Orange Trail. Probably my favorite local falls because they are not overrun with people.

I had beautiful weather for this hike!! It has 3 main ascents, but nothing overwhelming, and all 3 have rewarding views at the top. I chose to park at the Alander Mountain Trail Head and then bike a little under 3 miles down East Street (mostly gravel) to the Mt. Frissell Trail Head and just locked my bike up there. This hike can be a loop if you walk down East Street if biking isn't an option. When you start the ascent of Alander Mountain, you have to be careful not to miss the turn on the trail. The nice wide trail that you will have been on for quite awhile continues straight towards the NY trail head of the South Taconic White blazed trail, but you need to make a right turn to head towards the peak of Alander Mountain. The descent down the otherside of Alander Mountain on the Alander Mountain Trail is a nice end to the hike.

nice hike it was very foggy in the morning so we had no views from near mountain. but after bear mountain we continued to a ravine can't remember the name but it had some nice waterfalls and nice hike, then up to I think race mtn with some nice views and finally down to race brook falls, which was very cool by now we were beat and ready to get to car. overall nice hike and well marked and being partly on the AT we got to meet some cool people from all over the country.

Be prepared for a really quick intense rock scramble! Starting from here will give you a serious workout before you loosen up... highly satisfying and you will meet some great through hikers. Bring some trail magic.

3 months ago

We do this trail every summer and it never fails to please. Even the hard part has started feeling easier. Definitely more overgrown this year!!

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