The tiny state of Connecticut is home to dense forests, winding rivers, and lovely hiking trails. A stunning portion of America’s most famous trail, the Appalachian Trail, even runs through the northwest corner of the state. While this corner has some of the best hiking trails in Connecticut, it certainly doesn’t have a monopoly on CT hiking. There are fantastic options throughout the whole area. When most people envision Connecticut, they typically think of affluent suburbs on the sea, but a hike offers a totally different perspective of a state that’s full of diverse landscapes and outdoor adventures. Here are our votes for the 18 absolute best hikes in the Constitution State.
Exploring Connecticut With Let’s Roam
There are more than just hiking trails in Connecticut! From ritzy bedroom communities to vibrant cities, the Nutmeg State is a fantastic place to explore, and we’re here to help! We’ve created a huge list of sightseeing scavenger hunts to help you discover CT. Our hunts are a combination of a traditional scavenger hunt, trivia game, and photoshoot. Complete photo or video challenges at each spot to earn points! At the end of the route, you’ll see how you stack up against our citywide leaderboard. It’s a fantastically fun way to get familiar with a new city!
Exploring Connecticut’s Hiking Trails
Most of the trails in Connecticut (except a couple of portions of the AT) are easy to moderately challenging. While you’ll need a sturdy shoe, most of the trails on the list won’t require any more equipment or technical skill than that.
The best time of year to hike in Connecticut is arguably the fall. New England is famous for its fall foliage, and the trails of CT are the perfect spots to get lost in a sea of reds, yellows, and oranges. Many locals also find the trails fun in the winter, as many can be traversed by cross-country skiing or snowshoeing. Summer is nice weather-wise, but it can be a bit buggy, so if you don’t like gnats, you better bring some DEET.
The Best Hiking Trails in Connecticut
On this list of the best Connecticut hiking trails, we’ve tried to include something for every level of hiker. We’ve gathered some epic day hikes and some backcountry, multi-day treks, too. From easy strolls to thigh-burning challenges, Connecticut has a trail for everyone. Here are a few of the best, in no particular order.
1. Air Line State Park Trail
Air Line State Park Trail is one of the many great hikes in the park of the same name. It follows an old railroad route linking New York to Boston. The trains are long gone these days, but the trail remains. It’s a point-to-point trail traversing 43.3 miles, spanning from Thompson to East Hampton. It’s a moderately challenging route and usually takes between 14 and 15 hours to complete. The multi-use trail is comprised of packed dirt and gravel, so it’s appropriate for hikers but also easily tackled by even beginning bikers and horseback riders.
Most of the trail is shaded and treats the hiker to mountain views, wildflowers, some small streams, viaducts, and interesting rock formations. Part of the trail near the southwest end is wheelchair accessible and can be accessed from the parking lot off Main Street. In fact, you can access portions of the trail from nine Connecticut towns!
2. Ragged Mountain Blue and Red Blazed Loop
The second amazing CT hike on our list is Ragged Mountain Blue and Red Blazed Loop, which is near Berlin. At just 5.6 miles, it’s much shorter than the last entry. The loop trail generally takes 2.5 hours to complete and is popular with birders, bikers, and hikers.
The trail is rugged but offers glorious vista views over the Wassel Reservoir. While the fall foliage is a sight to see, winter hikers strap on snowshoes and tackle the trail, as well. It’s beautiful year-round! There are three popular trails at Ragged Mountain. The blue and red loops are rocky and more rugged. The orange trail is smoother. While they are all lovely, the blue and red loops feature towering bluffs, a small waterfall, and vernal pools. Though the trailhead is located smack dab in the middle of a neighborhood, it doesn’t take long to get lost in nature on this trail. It’s a quiet spot to commune with the outdoors.
3. Sleeping Giant State Park Tower Trail
Now, we head to Hamden for a 3.1-mile out-and-back hike up the side of Mount Carmel. The Tower Trail is considered an easy hike and usually takes 1.5 hours to complete. You’ll trek up 739 feet to the summit of Mount Carmel and the 1930s observation tower. The four-story stone tower was built by the Civilian Conservation Corps and offers a fantastic view spanning from Long Island Sound to the skyline of New Haven.
The park does require a small parking fee for out-of-state vehicles, so bring some cash. The trailhead is located just across from Quinnipiac University in the picnic area. It’s a popular trail and picnic area and can get crowded on the weekends.
4. Bear Mountain Trail
Located near Taconic in Mount Riga State Park, Bear Mountain Trail is a 6.1-mile loop trail that is very popular with local campers. The trail takes just 3.5 hours to complete and is considered moderately challenging. Many choose to do it over a couple of days as a backpacking journey. No matter how long you take to get there, the panoramic views from the top are pretty impressive. Bear Mountain is Connecticut’s highest peak—or the highest peak that is completely inside the state. Mount Frissell is the highest, straddling the border of CT and Massachusetts. Anyway, the trail includes a few very rocky and steep segments. Be especially careful when climbing in winter, as part of the trail is often ice- and snow-covered. Also, be prepared for an elevation gain of 1,683 feet.
The trailhead is located just off Route 41 and has its own parking lot. If tent camping and mountain climbing sound a bit too extreme, wander the Undermountain Trail, and book a night at Bear Mount Inn instead!
5. Chauncey Peak Trail
Let’s hop over to Meriden for one of the best day hikes in Connecticut. Chauncey Peak Trail is a 2.3-mile loop trail that takes just over an hour to complete for the average hiker. It’s located inside Giuffrida Park and is considered moderately challenging. The trail begins with a waterside walk along the Bradley Hubbard Reservoir and then ascends Chauncey Peak, gaining an elevation of just 344 feet. From the peak and Lamentation Mountain, you can see Hartford and almost all the way to New Haven.
The trailhead is just next to the parking lot. Since the trail isn’t always well-marked, it’s advisable to download a map before starting. There’s a quarry on private property near the peak, so stay on the established trail. The trail is not technically difficult but is steep and has short sections of loose rock. Expect company! Chauncey Peak is a popular exercise spot for locals and their dogs.
If you want a more direct and challenging route up to Chauncey Peak, take the Mattabesett Trail. It’s steeper, with several rock scrambles. The route is about two miles, with several ups and downs and a nice flat stretch along a lake.
While Chauncey Peak does have really nice views, it won’t take long to complete, so it’s best paired with other activities in the area if you’re a visitor. We suggest hiking in the morning and spending the afternoon exploring the historic monuments of Meriden on our “Meriden Mystical Treasure Hunt.”
6. Roxbury Mines
Located in Mine Hill Preserve near Roxbury, this 3.4-mile loop trail is a favorite among local birders. It’s considered moderately challenging, and most hikers complete it in about an hour and a half. At the core of the loop lies a 19th-century iron-smelting facility. This makes for a unique hike that is both a beautiful walk and a journey through history. As you pass tunnels, chimneys, stone arches, quarries, and wells, stop and read the information signs that detail the iron-making industry of the late 1800s. You’ll also pass massive granite cliffs and a quarry site. Many of the stone churches and mansions of cities from New Britain all the way to NYC are said to be built from stone quarried here.
The trail is well-marked with blue blazes, but there are several small loops in the area to explore, as well. The Reservoir Loop is slightly easier if you’re looking for a leisurely stroll. If you’re a history buff, this is the best trail in CT for you!
7. Bee Brook Loop
If you’re looking for an easy day out in the pines, head for Washington Depot, and escape to the Bee Brook Loop Trail. Bee Brook is a 2.1-mile loop trail that you can complete in less than an hour. It’s extremely popular with locals for daily exercise and dog walking.
You’ll tackle a small hill just after the trailhead and enter a curvy section that meanders its way to the Shepaug River. You’ll stroll through the river valley on a flat, pine tree-lined path for the rest of the journey. The trail lies within Hidden Valley Preserve, and it’s a picturesque spot with a full canopy of shade, multiple water crossings with wooden suspension bridges, and a peaceful atmosphere.
8. Trails of Enders State Forest
Located in Barkhamsted, Enders State Forest is loaded with lovely loop trails. Popular hikes include Tunxis Trails, Beaver Brook, and Indian Council Caves. The Indian Council Caves trail is a 2-mile out-and-back trail that traverses dense forests, fields of flowers, and, of course, caves. It also includes a fun rocky portion that requires a short scramble over boulders. Beaver Brook trail is a bit longer at 2.6 miles, and the longest of the three is Tunxis Trail. Tunxis is approximately five miles, and it connects to the caves trail.
The trails of Enders don’t have any epic views, as they’re all within the forest, but they are fun day hikes. Due to the environment, the trails can get muddy and buggy, so plan accordingly. The trails are also fairly rugged and not overly maintained, so you may have to jump over some tree fallout and obstacles.
9. Blue Blazes to The Ledge to Pillars Trail
Located near Weston Connecticut in Devil’s Den Preserve, this series of trails covers nearly eight miles of loops. The preserve is laced with rugged trails, and hikers usually spend around three hours in the woods. It’s popular for birding, hiking, biking, and cross-country skiing. The preserve covers over 1,700 acres and is heavily wooded. The trails traverse rocky ledges, wetlands, and wooded canopies.
Recent hikers state that the trails are not well-maintained, but that’s part of the adventure! You’ll want to download the map from AllTrails or another hiking app and follow along, as there are no markings for significant portions. You may also have to clear some limbs and battle a few spider webs in the process. The trail can get muddy, and there are no restrooms or facilities, so pack appropriately.
10. Appalachian Trail: Salisbury to Jug End Road
As mentioned previously, a portion of the great Appalachian Trail runs through Connecticut. One of the most difficult but rewarding bits is the segment from Salisbury to Jug End Road. This 16.1-mile point-to-point hike is rated hard and includes an elevation gain of 4,038 feet. It generally takes at least nine hours to complete, so it’s a full day of hard labor!
The trailhead is accessed through Mount Riga State Park at the Bear Mountain Trail we discussed earlier. From there, you’ll summit Lion’s Head, Mount Everett, Mount Bushnell, Mount Race, and Jug End on a series of ascents and descents. You’ll start in Connecticut and end in Massachusetts, so you’ll need someone to bring you back to your car!
Hikes like this one are a more manageable way to conquer the AT. Most Americans don’t have the luxury of taking off work for a couple of months to conquer the whole thing at once, but by tackling shorter segments of the trail intermittently, you can eventually knock out the whole thing!
11. Lantern Hill Trail
After that last entry, we need a breather and a fun day hike to even things out! Let’s wander over to North Stonington for a 1.5-mile loop trail that is jam-packed with challenges. Lantern Hill Trail is a popular route with locals and is rated moderate, mostly due to the incredibly rocky terrain. Once you’ve conquered the 491-foot hill, you’ll have excellent views of the surrounding towns! We love this trail because you get a little of everything. There are rock scrambles, small ravines, towering cliffs, granite ledge squeezes, and stunning scenery.
Some hikers do complain that all portions of the trail aren’t well-marked, so again, you’ll need to use navigation in order to stay on the route, or you can wander out onto the adjoining trails for a full day of exploration.
12. Mount Frissell Trail
The trail to the summit of Mount Frissell is another one laced with steep, rocky paths and plenty of fun scramble segments. Located in Mount Washington State Forest in the very northwest corner of the state, the trail traverses 2.3 miles and can be completed by most in about an hour and a half. As mentioned earlier, Mount Frissell is Connecticut’s highest peak, so the trail is unsurprisingly steep, although it’s only an elevation gain of a little over 800 feet.
From the summit, there isn’t really a good view, but there are several overlooks that provide incredible views on the way up. The trailhead is easily accessed from the parking area off Mt. Washington Road, and it’s pretty much uphill and scrambles from there. You’ll need bug spray, sturdy hiking boots, and a sense of adventure!
13. Haley Farm and Bluff Point Loop
Let’s take a break from the scrambles and difficulty and transition to an easy shoreline hike. Located near Groton, Haley Farm State Park is traversed by a lovely loop trail. It’s not a working farm anymore, and it’s a peaceful environment. There’s also a 0.8-mile bike trail that’s popular with locals.
If you want to extend your day, you can cross over the bridge and join the Bluff Point Loop. This trail wraps across the peninsula through Bluff Point State Park and extends the trip to 9.4 miles. The whole trip typically takes about three hours and is considered moderately challenging.
14. Castle Craig Tower
Located outside of Meriden in Hubbard Park, the Castle Craig Tower hike is perfect for the whole family. The entire trip is just under three miles round trip and is easily conquered by even young children. The destination is East Peak and its interesting stone castle. While it does not hail from the Middle Ages, it feels like it, which is fun for the kiddos, too. The tower is just 32 feet tall, but it offers a panoramic view of the area.
The trailhead starts in the parking lot near Mirror Lake on the northwest side. There’s a secondary parking lot on the east side of the lake, as well. You’ll start out on White Trail, which is slightly wooded and runs along the highway. Cross over the pedestrian bridge, join Red Trail, and stay to the left. You’ll join White Spur Trail and then Metacomet Trail to finally meet the East Summit.
The trail system in Hubbard Park is pretty extensive, so you could make a weekend of it easily by taking the trail up the West Peak to the S. Overlook or branching off onto adjoining trails for a wander.
15. The Trails of White Memorial
The next amazing Connecticut trails on our list take us to Litchfield and the White Memorial Conservation Center. The reserve boasts 40 miles of trails that are centered around environmental conservation and ecology. The simple hikes are popular with birders, botany lovers, and wildlife watchers, as the 4,000-acre plot is home to a vast array of flora and fauna. Most of the trails are constructed of very well-maintained boardwalks and easy-to-traverse paths.
Stop by the White Memorial Nature Museum to pick up a trail map and enjoy the impressive array of natural education exhibits before your hike. They have live animals and interactive exhibits that provide extensive knowledge of the wildlife in the area.
16. Denison Pequotsepos Nature Center
Mystic might be famous for movies and pizza, but it also has plenty of opportunities to get outdoors in the Denison Pequotsepos Nature Center. There are about ten miles of trails that crisscross the nature center through meadows and forested land. Like White Memorial, Denison is also heavily focused on conservation and environmental education, so it’s a wonderful place to stretch your legs, walk off that pizza, and learn some useful information while you’re at it.
After a wander in the nature reserve, head back to the town of Mystic, and whip out your phone for a fun-filled adventure of trivia and photo challenges on our “Mystic Mysteries” scavenger hunt!
17. Nipmuck Trail
In the northeast corner of the state, another Connecticut state park presents epic hiking trails through Nipmuck State Forest. Bigelow Hollow State Park is located near Union and boasts an impressive trail system. Most avid hikers opt for the Nipmuck Trail. The full trail is quite long and considered challenging, running 41.5 miles from the city of Mansfield to the Massachusetts border. However, a portion of the trail traverses Bigelow Hollow State Park and is a popular day hike.
From the park entrance, you’ll head toward Breakneck Pond on a 6.7-mile out-and-back adventure. The trail presents you with water views for most of the journey and fascinating rock formations, too. It’s an incredibly beautiful trail in the fall season!
18. Macedonia Ridge Trail
Our last hike on the list takes us to Kent and Macedonia Brook State Park. The ridge trail is a great hike and offers a serene park atmosphere with panoramas over the Hudson River Valley, the Catskills, and the Taconic Mountains. The trail is 6.5 miles from the trailhead and spans most of the park. You hike to the top of Copper Mountain, stroll alongside babbling brooks, and enjoy the shade of lush greenery. The trail is very rocky and has several steep segments, both ascending and descending. Wear sturdy shoes, and bring your bug spray for this one!
Time to Hike!
That should be enough fuel to light a fire on your Connecticut adventure planning! “The Best Hiking Trails in Connecticut,” like all “best of” lists, is pretty subjective territory, but we hope you found something that piqued your interest on the list. What we know for sure is that Connecticut is bountifully beautiful, and you will never regret taking a few hours to explore its nature on foot! So, grab your boots. Dig through the closet and find your poles, and hit the trails as soon as possible. Just don’t forget the bug spray, and remember to check for ticks!
After all that hiking, you’re going to need a comfy spot to lay your head! Here’s our list of “The 15 Most Unique Places to Stay in Connecticut!”
While hiking in Connecticut is awesome, there are some seriously epic trails to tackle in the rest of our great nation! Take a look at “The Best Hiking Trails in the U.S.” to plan your next big adventure.