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.

Fairly gradual hike up an wide, dirt road. We went on one of the first warm days of Spring, and the crowds were unbelievable. The tower at the top felt like a party, with probably 50 people crammed onto the top level. This would make a decent hike on a day with less people, but it wouldn’t be phenomenal.

I went a couple days after a significant rain event, and the trail wasn't that fun. it was basically walking uphill in a swampy stream. There are small rocks throughout the trail that make it very easy to twist an ankle. Definitely recommend proper foot wear.

The tower at the top is very nice, but I probably wouldn't do this particular hike again.

Enjoyable, I'll try it again in the summer for hopefully better scenery.

I live 5 minutes away and I absolutely love this place!! Many different options for a hike...trails link up with Michael Ciola Conservation Area as well. Well maintained trails..blazed really well and also numerous spots to sit and enjoy lunch. I will be back for sure!!

Can't get to the trail head, all posted land.

Great spot! Check the additional “hardscrabble trail” loop off the purple and white trails.

Hiked the tower trail on Sunday- it was VERY icy, but that made it more challenging and fun.

Nice hike with family. Very busy, which is a pro and a con. Great for dogs as there were a bunch of dogs on this trail. Nice views from the tower.

Perfect hiking weather the day we chose to hike this well marked trail. Challenging yet fun trail. Was surprised that we did not see another hiker the entire trek. Well worth checking the trail system out.

Great place to go for a hike and just the right distance to walk. Bring water and if you have a dog with you bring water for him too, very important.

Well marked trail

Beautiful view when you reached the tower!

Tough trail in spots - especially the climb up Mt Everett from the south. Beautiful scenery that is always changing during the hike. Sages ravine was especially beautiful.

Absolutely beautiful scene once you hike to the very top. Breathtaking view once the leaves start turning color. Easy hike for all levels.
Many events scheduled throughout the Season.

The trail itself was not a strenuous hike and is very doable for those that are looking for something less intense and short. It isn't very well marked, as we found out to indicate that you are on the correct trail, so so keep an eye on the markers and if possible use an app that tracks routes.

The Housatonic Overlook made the hike a 4 star. In addition, there was enough challenging terrain to have us feel the hike which we like. We got a late start so only went in about 2.5 Miles. Good hike overall.

4 months ago

We picked a perfect day to hike this trail. The trail is well marked but you need to pay attention due to several intersecting trails. We did the trail in 4 hours and 15 minutes.We did not see another soul during the trip,

Moderate/easy hike on the AT! Most sections of the hike are flat. I really loved the spot at Rand’s View- definitely has to be one of the best viewpoints on the CT AT (it’s featured at the REI in Milford likely for that reason). Would definitely recommend!

Scenic hike and beautiful views from the top at the tower!!! Great photo opp!

Amazing view at the top, does get a little muddy along the trail if it has rained.

Went up to the Tower and a loop through the blue/orange/red/green/white trails. Leaves aren’t changed yet, so if you’re looking for colors wait a week or two more. Be careful of the fallen leaves obscuring the trail. Keep an eye out for markers if you’re not using AllTrails and GPS.

This is a gentle sloping run of the Natchaug Trail emptying into the Nipmuck. There is a campsite at the transition between trails and camping is available year-round. From camp it is a gentle downhill hike out to Perry Hill Rd.

Usually very very popular on weekends, but the path is easy to follow and great views when you get to the top.

5 months ago

Took the Tower trail up to the Tower then continued down the Blue trail, cut back on the green, and returned on the yellow. Great easy going hike with a few challenging spots. Next time I would do this path in reverse to make it more challenging. The Blue & Green part of the trail are a little steeper and more technical than the Tower trail.

Good day hike but you can camp out overnight in a tent or in the shelter at 10 Mile River.

6 months ago

Nice hike. If you're planning on camping overnight you're supposed to register for it. I was there Sep 16, 2017 there wasn't any good places to filter water so plan to pack a lot of it. Also be on the look out for broken glass, some jerks have brought glass bottles out there and broken them along the trail. LNT

A very senic, challenging and rewarding seciton of the trail. While the elevations do not appear to be very intimidating, the grades involved make this very challenging. Do not underestimate this section of the trail.

wide gravel trail, doable with a trail stroller, and good for kids, very easy, crowded, just note the length. it's cool because it takes you to the tower, but there are much better hiking trails there.

6 months ago

Backpacked through this in one day. My original intention was to use this as a testing ground to see how well I'd do with backpacking. For a first time hike with an extra 40lbs worth of backpack, I'd say it was difficult. Without the added weight I would guess that this would have been a fairly easy trail. There is a long portion of gravel road in the middle that does get a little boring, but for what I wanted to learn I'd say this was an excellent hike.

Load More