The 17 Best Hikes In Connecticut to Experience (2024 Guide)

Connecticut is one of the most hiking-friendly states in the country. According to the state’s 2020 Forest Action Plan, over 60% of CT is covered in forests. Connecticut also ranks high for urban greenery, meaning most residents live within a short distance of a park or state forest.

Most of Connecticut’s best hiking spots don’t require you to be an outdoor pro or in athlete-quality shape. There are plenty of mellow adventures for even a casual hiker to enjoy.

And the great thing is hiking is an excellent free thing to do in Connecticut, letting you enjoy this beautiful state without spending a fortune.

Let’s look at where to find some of the best hikes in Connecticut.

The Best Hikes & Trails to Check Out in Connecticut

Kent Falls State Park

Kent, CT

There are over 100 state parks in CT. Kent Falls is near the top of the list in terms of visitors, and it offers one of the best hikes in Connecticut. What makes it such a popular destination is the 250-foot waterfall. This natural water feature is not a straight drop. Instead, it slowly cascades over several stages.

The hiking trails at Kent Falls State Park allow you to climb alongside the falls, grabbing great views of the water at each tier. There are observation decks at various vantage points of the falls and the surrounding environment.

While the trails are incredibly well maintained, including paved portions, you should be careful of mud or ice at certain times of the year. Otherwise, this is a very easy hike that even children can enjoy. Plus, you can’t beat seeing such a majestic waterfall!

Judges Cave (West Rock Ridge State Park)

New Haven, CT

Just outside of New Haven, there is an interesting piece of history to accompany a 1.8-mile hike. The trail to Judges Cave is easy, with only a slight incline as it snakes its way to the caves. Once there, you can explore the inside of the caves.

Now for the history side of things. The name for this rock formation comes from two judges, Edward Whalley and William Goffe, who hid in these caves in 1661. The two men were trying to escape the Crown after they (along with 56 other judges) signed the death warrant for King Charles the First. His son, King Charles II, was determined to find and execute the men responsible for his father’s beheading.

As the story goes, Goffe and Whalley hid in the caves for weeks until making their way to Hadley (MA) by night. A plaque at the site commemorates these events and the historical place of Judges Cave.

While reaching Judges Cave is not a demanding hike, the site is part of a larger state park. For those looking for a longer hike or more challenge, Rock Ridge State Park includes a nearly 8-mile loop you can walk.

Haystack Mountain State Park

Norfolk, CT

A few hikes in Connecticut end near a lookout or tower, like Talcott Mountain State Park’s Hublein Tower or Castle Craig in Meriden. These structures grant you 360-degree vistas of your surroundings.

The Haystack Tower is one of the best examples of these tower views. Not only are the surroundings incredible to take in at the top, but the structure itself is beautiful. It almost feels like it is straight out of a fantasy novel.

Haystack Mountain is 1,683 feet above sea level. The hike is an incline of about 500 feet (plus a few more to reach the top of the tower). Overall, it is a moderately easy adventure with a great, picturesque ending. Be sure to follow the yellow trail markers to reach the tower. Otherwise, it’s easy to find yourself on the wrong path.

Castle Craig & Hubbard Park

Meriden, CT

If you’ve already seen the fairy-tale-like Haystack Tower, you can up the ante with Castle Craig in Hubbard Park. The tower and foundation seem entirely out of place, adding to the mystique of the location. The park and Castle Craig were both constructed and donated to the town by Walter Hubbard.

Hubbard traveled a lot and loved European castle architecture. He wanted the people of Meriden to experience the same sights he had seen overseas. It really matches the medieval feel perfectly!

Hubbard Park is a sprawling green space with plenty of paved walking paths and room to gather with friends. If you want to check out Castle Craig, several trails lead to the structure, each with varying degrees of difficulty. This allows you to pick how hard a hike you want to enjoy.

Sleeping Giant State Park

Hamden, CT

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If you’ve been to Castle Craig before and taken in the view from the tower, you may have spotted an interesting natural shape on the horizon: the Sleeping Giant. Named because the curves of the mountaintops resemble a slumbering behemoth, it is one of Connecticut’s most known and recognizable hiking destinations.

Across the expansive natural landmark, there are over 30 miles of hiking trails. These hiking options range from mellow and easy, to challenging and strenuous. So, plan your exploration of the Sleeping Giant carefully. You’ll want to study the trail maps and pick your route based on the weather and your skill level.

No matter what trail you take, you can expect incredible views of the surrounding area. On a clear day, you can easily look out to Long Island Sound or spot downtown New Haven.

Bear Mountain

Salisbury, CT

While Sleeping Giant gets a lot of acclaim because of its interesting shape, Bear Mountain gets the credit as the highest peak in the state. This fame makes it a popular hiking spot. Plus, the views at 2,323 feet are pretty incredible! That said, it is more challenging than many other CT hiking spots on this list.

The other reason Bear Mountain sees a lot of traffic is its connection to the Appalachian Trail. You’ll access Bear Mountain through Mount Riga State Park, eventually turning onto the Appalachian Trail. The hiking at this portion definitely gets a degree harder. You’ll want to pay close attention to your footing at each step.

The summit of Bear Mountain offers the 360-degree views that every hiker loves. As the highest peak in Connecticut, you won’t find a better vantage point to take in the sprawling landscapes, rivers, lakes, and other features of this great state.

It’s worth mentioning that Bear Mountain is only the tallest peak in the state, it’s actually not the highest point. The neighboring Mount Frissel (it’s just a few minutes from Bear), which spans the border between Connecticut and Massachusetts, has the tallest point you can reach in CT. The peak of the mountain is in Massachusetts, giving Bear Mountain the fame.

West Thompson Lake

Thompson, CT

The trails at West Thompson Lake don’t feature many steep inclines, giving it the appearance of an easy hike. However, the loop around the lake is over 7 miles, so it should not be taken lightly. With the lake in the center, there aren’t any shortcuts to making your way back to the parking lot!

That said, the 7.2 miles won’t seem so bad when you have beautiful Thompson Lake by your side for the entirety of the hike. It’s the perfect way to spend a sunny day. The trees along the shore give you plenty of shade, but you can still enjoy the rays as they poke through the canopy.

West Thompson Lake is also great for camping, fishing, boating, and more. You can really turn this hiking adventure into a day-long excursion, or more, if you decide to camp for the night!

Hidden Valley Preserve

Washington, CT

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Hidden Valley Preserve makes the list because of the Thoreau Bridge. This is a massive cable and wood suspension bridge over the Shepaug River. It actually connects two sides of the gigantic nature preserve. In total, the bridge is 134 feet long. Etched into the wood are quotes by Henry David Thoreau.

While this suspension bridge is what draws people to the Hidden Valley Preserve, this site offers plenty more. It is over 600 acres of land that incorporates trails of all difficulty levels. Depending on which paths you take, you may spot old railroad foundations, an old quarry, and many other interesting structures, rock formations, etc.

Hidden Valley Preserve is a place you’ll keep coming back to time and time again. Even after many trips, you still won’t see everything the land has to offer.

More Top Hiking Spots In Connecticut

This list contains some of the most popular and well-known hiking spots in CT and a few hidden gems. However, there are hundreds more ready for you to explore. After all, the state is home to over a hundred state parks and forests!

If you’ve hiked every spot on the list or want to try something closer to home, here are a few more of the best hiking spots in CT.

Spruce Brook Falls (Beacon Falls, CT)

Swan Hill (Higganum, CT)

Little Laurel Lime Park (Seymour, CT)

Pauchaug State Forest (Voluntown, CT)

Pine Mountain (Ridgefield, CT)

Herrick Trail (Sherman, CT)

Mine Hill Preserve (Roxbury, CT)

Bluff Point Coastal Reserve (Groton, CT)

Harkness Memorial State Park (Waterford, CT)

Remember, whenever you’re out on the trails, pay attention to where you’re putting your feet, and always bring plenty of water and supplies, especially for longer adventures.

Happy hiking.

Have any questions about or additions to our guide to the best hikes in Connecticut? Share your thoughts by commenting below.

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