Are you looking for longer hikes in Connecticut? Hikes with views, stone walls, waterfalls, rivers and streams along the way? Fields of green and grassy meadows on one side of a well worn narrow path with the Housatonic River on the other? Then a classic New England hiking experience awaits you along the 50 miles of the Appalachian Trail in CT in the northwest corner of the state.

Jared, the dogs, and I hiked the whole AT in Connecticut by breaking it into seven different hikes. In this blog post I will show you how to break down the 50 miles into seven manageable (moderate) hikes including maps and All Trails links for each of the 7 legs so you can navigate yourself! Of course, the 50 miles can be broken up a few different ways and some people might even hike it in two days! (I ran into a group that was trail running the entire thing in one day!) I like hiking to be challenging yet enjoyable, so I prefer moderately sized hikes but feel free to combine a couple if you’d like to complete it in less time!

Did you know that the Appalachian Trail is actually the longest (at 2,193 miles) hiking-only footpath in the whole world, running from Georgia to Maine?! And we are so lucky to have a portion of it in our state. This part of the state is about an hour and 20 minutes from Hartford so wherever you are located in CT, you can definitely make any of these hikes a day trip destination. And it’s worth it because you will get to see some of the best views in CT along the Appalachian Trail.

This is the first hike along the Appalachian Trail in CT. You are treated to nicely laid rocks for stairs and a little incline at the start before you come down to the Housatonic River. Look out for Tenmile hill shelter in a wide open field if you want a shaded spot for lunch. The bridge you cross has just a few steps up to it but it is a little steep. Once over the bridge you can stop for a quick break by the river.You’ll then continue the final stretch of this hike with the rushing river on your right. There is no big peak with views here, the water is the main attraction! It is a great start and welcome to your journey along the AT in CT. 

Leg 2 Bull’s Bridge to Macedonia Rd, South Kent ~7.3 miles, 1900 ft of elevation

A big chunk of the incline on this hike is right in the beginning. So try not to eat too much on the ride over and rather wait until you get to a nice view right after the initial climb. Climb up about 800 ft and you reach the top of Schaghtichoke Mountain which offers sweeping southeast views. You will now stay up at this elevation for the most part walking along with minor dips here and there, a stream crossing and a tent site. The descent to the road is a little steep but you’ll be glad to see your car and complete this second leg of the journey.    

Leg 3 Macedonia Rd to River Rd, Kent ~4.7 miles, 1362 ft of elevation gain

You’ll love the start of this hike. Entering a big field that takes you across a little stream and let’s you settle in before you begin a modest little climb of 500 feet that will get your heart pumping. The highlight of this hike is for sure Caleb’s Peak with wide open views to the east and then also St John’s Ledges which you will walk along at the end of the hike. The slabs are slabs of rock (that you walk along, no up!) are about 100 feet high and are named after their owner in the 1800s, Timothy St Johns.

Leg 5 Pine Knob to Sharon Mountain to Rt 7, Salisbury ~10.7 miles, ~2600 ft of elevation gain

This is a big one so pack lots of snacks and water! You’ll start with almost 600 ft of elevation gain here which takes you up to Pine Knob Lookout (great place to watch the sunrise)! Continuing on you’ll have several ups and downs until you get to Sharon Mountain. This is another great view and good place to sit as long as you don’t mind the sound of the racing cars below at Lime Rock Park! You will definitely feel a sense of accomplishment after this hike and hopefully have lots of beautiful pictures to go through.