Hike the Appalachian Trail in Connecticut – 50 Miles in 7 Manageable Sections Last Updated: September 2022

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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? A classic hiking experience awaits you along the 49 miles of the Appalachian Trail in Connecticut in the northwest corner of the state.

Here's how to break down those 49 miles into 7 manageable (not too difficult) hikes and navigate each of the 7 legs.

Of course, the 49 miles can be broken up a little differently. Some people might even hike it in 2 days! (I ran into a few people that were trail running the whole entire thing in one day!) I like hiking to be a challenging yet enjoyable experience, so I prefer moderately sized hikes but feel free to combine a couple if you’d like to complete it in less time.

 

Trail History

Just a little history, 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 in Connecticut, 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 Connecticut.

Note: These are all 2 car hikes, meaning you leave one car at the start and one at the ending point, so you don’t have to hike all the way back. If you are hiking solo, then you will need to double your miles and hike back! To do these point-to-point hikes, first drive to the ending point and leave a car parked there. Then hop in the other car with your hiking partner and drive and park at the starting point. You are now ready to begin your Appalachian Trail Connecticut hike!

The hikes are listed in order, south to north, but you can reverse the order and hike north to south if you’d like. Let’s get started:

Leg 1 — Hoyt Road to Bull’s Bridge, Gaylordsville

~4 miles, 800 ft of elevation gain

This is the first hike along the Appalachian Trail in Connecticut. 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 Connecticut.

 

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 lets 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 made of rock (that you walk along, not up!) are about 100 feet high and are named after their owner in the 1800s, Timothy St Johns.

 

Leg 4 — River Road to Pine Knob Loop Trail, West Cornwall

~8.45 miles, 1400 ft

You’ll love the stretch of trail, the longest stretch of the Appalachian Trail that runs right along the Housatonic River. Taking you through a wide-open field with mountain views on the left, the river will be on your right, and it will be like this for a few good miles! In fact, the first 4.5 miles of this hike is pretty flat. After this, you will hike up some elevation and at the end come down along the raging falls at Pine Knob Loop.

 

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.

 

Leg 6 — Route 7 to 44 Salisbury

~8.46 miles, 1400 ft of elevation gain

This hike might turn into a favorite as it combines a bridge crossing with a waterfall sighting and 2 views – one of which seems to come out of nowhere. You’ll start by walking along a quiet road in Amesville, crossing a bridge and seeing a top Connecticut waterfall called Great Falls! After this, you will begin a long, steady climb to Mount Prospect. Take in the views here but don’t spend all your free time in this spot because a little while later you will run into one of the best and most unique views in Connecticut, Rand’s View. What makes it so special is how you come to it, emerging from the woods to a view so wide, a panorama shot wouldn’t do it justice! After this, keep your eye out for and get a picture with Giant’s Thumb and then continue the rest of the (relatively flat) way to the car.

 

Leg 7 — Rt 44 to Bear Mountain

7.2 miles, 1900 ft of elevation gain

On the final leg you have a bit of a steady climb, but you are treated to two peaks, one of them (Bear Mountain) being the tallest mountain in Connecticut. And like a bear you will kind of be using all fours here to reach these two peaks. Part of the trail that takes you up to Bear Mountain goes through Mount Riga State Park in Salisbury. But before you get to the tallest mountain in Connecticut, you will see and enjoy the eastern facing views at Lion’s Head. There is a little scramble up rocks right before you reach Lion’s Head, and you will experience a similar climbing experience on the way down from Bear Mountain’s summit. I love bringing a hiking pole (or two) to help brace myself on the way up or down these steep sections. After Lion’s Head you’ll head to Bear Mountain and be sure to climb the pile of rocks there and see the views in the distance.