The Best Hiking Trails in Connecticut

Even though it’s one of the smallest states in the US, Connecticut boasts a diverse selection of trails for every level of hiker. If you do love exploring the outdoors by foot, one of the major perks of Connecticut being a geographically small state is the fact that you’re never far from amazing trails that will bring you to peaks with glorious views and near waterfalls that will take your breath away! No matter what kind of trail experience you’re looking for – a full day in the woods, a leisurely walk near a lake to spot some birds, or a chance to visit some historical sites – you’ll be able to find it in Connecticut. It might be an unassuming state to some, but once you lace up your hiking boots and head out to any of the wonderful spots on this list we put together for you, you’ll quickly discover just how much natural beauty this fine state has to offer.

Top Hiking Trails Around Connecticut

Wadsworth Falls Loop

The Wadsworth Falls Loop is definitely a trail you don’t want to miss out on when in the Middletown region. Rated as an easy hike, this 3.6-mile loop trail snakes through the gorgeous surroundings of Wadsworth Falls State Park, offers excellent opportunities for birding, and leads hikers to the magnificent namesake waterfall that cascades over sandstone ledges.

During the hike, explorers can keep their eyes peeled for birds like the red-bellied woodpecker, bald eagle, great blue heron, and blue jay while enjoying the serene sounds of the babbling water and the scenic views from the various overlooks. Wadsworth Falls Loop is a popular and well-maintained trail that’s suitable for hikers of all skill levels, making it a perfect choice for anyone looking for a relaxing and picturesque outdoor adventure.

Chauncey Peak Loop

The 3-mile Chauncey Peak Loop, located in Giuffrida Park, is considered a moderate trail that rewards hikers with panoramic views of Crescent Lake and Meriden from Chauncey Peak and Lamentation Mountain. The trail features some rugged terrain, rocky cliffs, and steep ascents, but there are plenty of spots to take breaks and appreciate the stunning scenery along the way.

Due to the rocky nature of this hike, it’s best to come prepared with sturdy hiking boots and to avoid the trail after heavy rains. The views from the summit definitely make the effort well worth it, especially during summer and autumn when the forest is lush and colorful as can be.

Mattabesett Trail

For the extreme long-distance hikers and backpackers out there, the Mattabesett Trail is calling your name. This 65-mile-long trail is part of the New England National Scenic Trail and traverses through some of the state's most iconic and breathtaking natural surroundings. Hikers can expect challenging climbs, towering cliffsides, shaded hardwood forests, and pristine views of the Connecticut River. Highlights of the trek definitely include hitting the summits of Beseck and Pisgah Mountains, which allow hikers to take in vistas that go on for miles and miles.

Both day hikers and backpackers should be well-prepared when embarking on the horseshoe shaped Mattabesett Trail and note that the trail is blazed with blue rectangles and connects to the towns of Berlin and Middletown. Whether you're seeking a shorter section hike or a multi-day adventure into the wilderness, the Mattabesett Trail promises an exciting, stunning, and unforgettable journey through some of Connecticut’s greatest landscapes.

Bear Mountain Trail

The Bear Mountain Trail is one of the most popular and rewarding hikes in Connecticut that leads to the state's highest peak. This trail is a 6.1-mile loop, making it an excellent route for backpackers that want to camp among the dense forest and while surrounded by the Taconic Mountains. While it can absolutely be trekked in a day, the trail does have a steep ascent and is considered to be on the strenuous side, so only those that are confident in their hiking abilities should attempt the loop.

Bear Mountain Trail and its 2,316-foot peak provides a true wilderness experience with awe-inspiring views from the summit that makes the effort well worth it. Expect to see animals such as bald eagles, deer, woodpeckers, and hares during the journey, too. If hitting each state’s highest peak is on your to-do list, be sure to add the Bear Mountain Trail to your list if you haven’t conquered it yet!

Sleeping Giant Tower Trail

The Sleeping Giant Tower Trail is a 3-mile trail (round trip) that’s open year-round and takes hikers to the summit of Mount Carmel and the four-story stone observation tower, which was built in 1936, atop it. The trail is family and leashed-dog friendly and brings you through lush forest that bathes you in the tranquil sounds of nature.

The trail is marked well and great for every level of hiker, and the vistas of the surrounding woods, mountains, and towns from the observation tower make the climb especially worth it. While it’s an amazing hike any time of year, there’s nothing quite like the sight you’ll receive of the vibrant fall foliage if you visit here between September and November. Grab your hiking boots and camera for a day outdoors that you’ll never forget when you take on the Sleeping Giant Tower Trail.

Connecting with the Outdoors in Connecticut

The entirety of New England is brimming with natural beauty, and Connecticut is certainly no exception. Between the rugged terrain of the Mattabesett Trail to the more easy-going hike that the Wadsworth Falls Loop offers, each route on this list provides something unique while immersing explorers into peaceful surroundings that are teeming with wildlife and picture-perfect views. Time spent outdoors is always time well spent, especially when it’s somewhere as beautiful, historic, and diverse in landscapes as Connecticut.