6 Of The Best Hiking Trails In Connecticut

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Hiking in Connecticut brings varying landscapes and skill-level difficulties that will make you feel like a kid on Christmas day! Landscapes include steep mountain inclines, woodlands, old forests, lakes, and interconnecting trails. As an avid hiker, I thoroughly enjoy adventure and guarantee that you’ll find the same hiking in Connecticut.  

Hiking in Connecticut offers hiking trails for beginners, intermediates, and seasonal hikers. Top hiking trails are Wadsworth Falls Loop, Southford Falls Red Trail, Bear Mountain, Round Mountain, Mount Frissel, Brace Mountain. Landscapes include woodlands, old forests, muddy and icy terrain.

There are subtle differences between a good hiking trail and a great one. Although preferences may differ, Connecticut certainly has the gift of giving (hiking trails), so let’s find one that will satisfy the hiking desires of your heart.  

Hiking In Connecticut

Connecticut has one of the best variety in landscapes, seasonal hiking, and skill level alternatives. You’ll come to love them for their panoramic views and awe-inspiring mountain peaks. Your canine companions are welcome to join if they remain on their leashes, and some of these trails are perfect for joggers and cyclists,  too.

Beginners will enjoy fulfilling hikes in Southford Falls Red Trail, Southford Falls State Park. The walk consists of easy-to-handle inclines, streams, and rocks that make it a great introduction to hiking. Children of all ages will enjoy the hike, as would the elderly – there are even picturesque picnic areas along the way to stop and enjoy lunch together.

Intermediates hikers will have a great time at Mount Prospect And Raccoon Hill Via Appalachian Trail. There are several interconnecting trails for choosing the road less traveled, and each one provides interesting landscape changes that range from exceedingly rocky to wet and muddy or icy and slippery!

Seasoned hikers can find their fill at the Bear Mountain, Round Mountain, Mount Frissel, Brace Mountain trails. This magnificent trail connects four mountains and three states to bring the most panoramic vistas and strenuous hiking experience together. It is sure to put you through your paces as you ice skate down the icy slopes and steep inclines.

Connecticut Hiking Trails For The Whole Family

It’s time to step away from the digital devices, the books, the office, and live a little! Nature has a way of bringing relationships closer together, and family hiking trails can help you achieve that goal. Connecticut offers many spectacular trails that suit all ages and skill levels.

Wadsworth Falls Loop, Wadsworth Falls State Park

Wadsworth Falls Circular is a 3.6-mile widely frequented loop route with a cascade in Middletown, Connecticut, and the perfect trail for hikers of all abilities. The trail is best utilized from March to October and provides a variety of activities. You may bring your dog; however, they must be on a leash at all times.

Wadsworth State Park has two parking lots near the giant falls and the pond. A boardwalk allows you to cross the river and train tracks before heading into the woods. In reality, it resembles a deserted dirt road. There are no significant inclines or slopes, and the tread is excellent along the hiking track. This trail takes 1 hour and 42 minutes to complete.

After over two stone bridges, the walk ends at Laurel Grove Rd, across from the Wadsworth Mansion. Because it’s one of the first locations to get packed down after a blizzard, it’s a fantastic site to hike afterward. You’ll come upon a Giant Laurel as you progress down the route.

There are a couple of side routes, including one leading to Birch Ridge and another connecting to the pond. The trail contains a few muddy areas and leaf-covered tracks, so it may be a good idea to bring your hiking boots to avoid losing your footing. Because the trail markings are not always visible, it is essential to use an offline map for navigation.

This trail is an excellent climb in general, and if you go during the winter, you can expect to see a gorgeous frozen-over waterfall. Hikers, cyclists, and equestrians adore this trail. If you want to enjoy a more isolated and immersed experience, go early in the morning on weekends because it gets packed about 11:00 a.m.

Southford Falls Red Trail, Southford Falls State Park

Southford Falls Red Route is a 1.6-mile extensively-traveled circular trail with a lake suitable for all ability levels and exists in Southbury, Connecticut. The track is best utilized from April to October and is fantastic for hiking, walking, and jogging. This path is also suitable for dogs, and it takes 51 minutes to complete.

This easy-to-follow track contains the usual roots and pebbles. The slope changes a few times, giving you a few sharp inclines for great exercise! There may be a few muddy areas, so take care not to slide. You’ll have to crawl or walk over a couple of dead trees on the route if you don’t want to.

Because of the changing hues of the leaves, this route boasts some of the most stunning vistas. You’ll see bridges covered with eye-opening wildflowers along the journey, which makes for fantastic photo opportunities! In addition, the waterfall is beautiful, and the red trail is mainly near the water.

It may be a little rough on the route to the watchtower, adding to the trail’s difficulty, but the view you’ll receive once you reach there is well worth it. If you want to stop for lunch, there is also a fishing pond and picnic area.

Connecticut Hiking Trails For The Intermediate Hiker

Connecticut has plenty of challenging hikes for the daring, too! Most trails also permit canine company provided they have their leashes on at all times –  together, you’ll be conquerors! They’ll get the heart pumping and ensure that you work up a satisfying sweat.

Metacomet Trail Loop, Ragged Mountain Memorial Preserve

Metacomet Route Loop is a 3.9-mile loop trail with a lake and moderate difficulty in Berlin, Connecticut. This hiking trail is a fantastic option for hikers, walkers, joggers, and nature walks. Furthermore, dogs on leashes are also allowed to accompany their owners. It takes 2 hours to finish the path.

Beautiful views, as well as some challenging hills and descents, abound on this course. The route is typically well-marked; however, some sections may be challenging to follow due to imprecise markings. If you want to explore Galway’s side paths, you’ll need to cross streams, so bring poles and hiking boots!

It’s also worth mentioning that hiking this route in the fall requires extra caution because the leaves and mud create an added layer of slickness. The track is one of the rockiest in the area, with steep descents, so keep an eye on your ankles!

There are multiple spectacular views of the Upper and Lower Hart Pond on the climb up, with the peak being magnificent. The ascent is moderate, and there are several lookout points along the way. Although there is little contact with other hikers, it may get busy, so arrive as early as 08:30 if you want to get the most out of your experience.

Mount Prospect And Raccoon Hill Via Appalachian Trail

Mount Prospect and Raccoon Hill via Appalachian Path is a 6.2-mile moderately trafficked out-and-back trail with a waterfall in Falls Village, Connecticut. The route is best utilized from March to October and provides a variety of activities. Dogs can participate as long as they remain on their leashes. The trail takes 3 hours and 25 minutes to complete.

This Rand’s View hiking trek is unlike anything most hikers have experienced before. The Appalachian Trail is the main trail to follow for most of the hike, with modest inclines. The climb continues past the lovely vista at the summit of Mt. Prospect, which might be a stand-alone stop on a regular trip.

It descends the other side of the mountain, emerging from deep woodlands into a vast meadow that will certainly impress you. The low grass continues forever, providing a panoramic picture of the Berkshires beyond. Hikers searching for leisure time or a good picnic would love this location.

The walk is straightforward, and a map is not necessary. The half-mile detour to an Appalachian Trail shelter location will undoubtedly be a significant hardship. After that, you’ll descend to the camping spot along a mountain creek.

Many gorgeous wildflowers, large boulders, and a diversity of terrains decorate the trail, and you’ll be pleasantly delighted by the starry-lit night sky if you hike at night. The majority of the walk through the woods has a lot of shade, so plenty of water and plenty of shade on a hot day will surely motivate you to keep going.

Connecticut Hiking Trails For The Born Mountaineer

Every stride carries a prolific meaning for the hardcore hiker to empower them to overcome challenging trails! If you’re aching for a heavily-demanding hike, Connecticut can oblige you with inclines, descents, streams, and a great workout. It’s time to wipe down your hiking boots because your next adventure awaits!

Hemlock Hills, Pine Mountain Trail, Bennets Pond State Park

Hemlock Hills and Pine Mountain Path is a 7.5-mile, frequently-traveled circular trail with a lake classed as harsh and situated in Ridgefield, Connecticut. It’ll take you 3 hours and 52 minutes to finish.

The path is best utilized from April to October and is mainly for hiking, jogging, mountain biking, and snowshoeing. This route is also suitable for dogs, although they must be on a leash at all times.

Pine Mountain Reserve, located near Ridgefield, Connecticut, is a 368-acre open space. It will stretch fourteen miles from Bethel’s Terre Haute to Danbury’s Rogers Park, via the Charles Ives Homestead, and then south through Tarrywile Park. There are several trails, trailheads, and one of Ridgefield’s highest peaks in this area.

It will then continue southwesterly across Route 7 and through Wooster Mountain State Park to Ridgefield’s Bennetts Pond Park and Pine Mountain Park’s current trail networks.

The Charles E. Ives Trail gets its name from a famous composer. Ives, born in Danbury in 1874, was famous for his innovative classical works. In 1947, Charles won the Pulitzer Prize for his Symphony No. 3 and held the honor of being Connecticut’s state composer.

This hiking trail can be challenging to navigate because some sections are unclearly marked. As such, you must download a map and keep a close eye on where you’re going.

Bear Mountain, Round Mountain, Mount Frissel, Brace Mountain

Bear Mountain, Round Mountain, Mount Frissell, and Brace Mountain is an 11.6-mile moderately-trafficked circular path that offers magnificent views and rates as a strenuous hike. It exists near Salisbury, Connecticut.

The path is best utilized from April to October and is mainly for hiking, walking, and backpacking. This hiking trek should take 6 hours and 32 minutes to complete. Dogs are welcome to attend as long as they are on a leash.

If you want to save Bear Mountain for last when ascending the west side rather than down, you can start counter-clockwise. If you try to climb down the mountain’s west side, you need to be especially cautious since it might be pretty icy.

The trek includes numerous steep inclines, long scrambles, and climbs, but the spectacular vistas are worth it. There are a few overgrown trees and muddy slopes in certain spots, but nothing an expert wouldn’t be able to manage!

This path is one of the few that allows you to climb four peaks and span three states. You should expect a sharp descent from Bear Mountain, and at the bottom, keep an eye out for the Round Mountain cross path.

It will grow considerably steeper as you travel from Round Mountain to Frissel, so keep an eye on your balance. It will start to narrow as it gets closer to Bangle. Three miles of ancient woodland terrain await you!


Families will find Wadsworth Falls Loop in Wadsworth Falls State Park incredibly appealing thanks to slight inclines, fishing, and picnic areas. Hiking enthusiasts looking for a challenge will meet their matches at Metacomet Trail Loop in Ragged Mountain Memorial Preserve and the Bear Mountain, Round Mountain, Mount Frissel, and Brace Mountain interconnecting trails.