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Hike the Appalachian Trail in Connecticut – 50 Miles in 7 Manageable Sections

Meet our #CTcreator Kristen Valenti of Early Bird on the Trail! is proud to partner with some of the region's most popular content creators for ideas, insights and inspiration from the people who are lucky enough to call Connecticut home, like writer Kristen Valenti who wrote this article which you can also check out on her blog. Article has been updated by the Connecticut Office of Tourism.

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 seven manageable (not too difficult) hikes and navigate each of the seven legs.

Of course, the 49 miles can be broken up a little differently. Some people might even hike it in two 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.

And even better, Connecticut was named #1 in the U.S. for hiking!

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 Road to River Road, 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 Route 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 Route 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 two 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 — Route 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.

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