10 Top Hikes in Connecticut

Despite its small size, Connecticut offers both local and visiting hikers a variety of trail systems to explore. The parks and forests scattered throughout the state have hundreds of miles of trail, and you can enjoy everything from easily accessible and well-kept suburban strolls to more rugged and technical backcountry hikes through secluded woods and hills. In the spring and summer, you’ll hike through lush greenery, and the autumn is particularly stunning with the multicolored blaze of the changing leaves. Grab your snowshoes or cross-country skis in the winter for a peaceful experience on the snow-covered trails. 

Mohegan Park Loop

  • Location: Norwich, CT, in Mohegan Park, 40 miles southeast of Hartford
  • Length: 1.9-mile round-trip loop
  • Difficulty Rating: Easy
  • Best For: A family-friendly loop on wide and well-maintained trails
  • Dogs: No dogs

Located just north of Norwich, Mohegan Park is a lovely and well-kept park with a variety of activities that the entire family can enjoy. The flat trails offer a pleasant way to explore the park on foot. If you’re looking for other activities pre- or post-hike, pack a lunch and enjoy it at the pavilion or picnic area or, in the summer, swing by the swimming beach located on the east side of Spaulding Pond. Visitors can also fish in the pond, and families with younger children can visit one of the two playgrounds by the lake. In the summer, you can also stop by the Veterans Memorial Rose Garden which features nearly 2,500 rose bushes—June is the recommended time to see the roses at their peak bloom.

The Mohegan Park Loop is easy-to-follow, yet feels far away from civilization. The trails are wide and well-used, and the loop can be done year-round, even in the winter, as the trails are marked with colored blazes. If hiking the loop counterclockwise from the Mohegan Park Center Lot off Mohegan Park Road, start on the Blue Trail heading south. This forested trail crosses a wooden footbridge over a small creek and passes some rock formations on the left. At its southern end, the trail comes to a junction with the Green Trail at the Lower Pond—this is an especially scenic spot in the fall. Continue on the Green Trail along an earthen dam before heading back into the woods. You will cross a red plank bridge and eventually connect to the Red Trail briefly before finishing your hike on the Inner Paved Loop around the shores of Spaulding Pond. The pond has several conveniently located benches where you can rest your legs and soak up the scenery before heading home.

Godfrey Pond Loop

  • Location: Georgetown, CT, in Devil’s Den Preserve, 19 miles northeast of Stamford
  • Length: 1.3-mile lollipop loop
  • Difficulty Rating: Easy
  • Best For: A beginner-friendly loop with some historic sightseeing
  • Dogs: No dogs

A trip to Devil’s Den Preserve offers options for both beginner and experienced hikers. The 1,756-acre preserve is the largest continuous preserve managed by the Nature Conservancy in the state of Connecticut. As such, it offers an oasis from the bustle of some of the other suburban parks and preserves in the area. The preserve features many miles of forested trails, ranging from the popular and well-used southern trails to the more challenging and rugged trails in the interior of the park. Paper maps are usually available at the trailhead, and it is recommended that you take one on your hike, as the trail system can be a bit confusing in places.

The loop around Godfrey Pond is one of the easier and more accessible hikes in the preserve. At just over one mile in length, this flat loop is an ideal outing for families or beginner hikers. For more experienced hikers, this can serve as a warm-up loop for a longer exploration of the park. From the trailhead, the loop starts on the Laurel Trail, a wooded trail that winds east and north toward Godfrey Pond. The trail then skirts around the east side of Godfrey Pond, a mill pond created in the 1700s. Godfrey Pond is a picturesque spot, and you may find yourself lingering in the area to take in the scenery. There is a bench at one end of the pond where you can stop for a photo or a snack. As you continue your loop around the pond, keep an eye open for the remains of an old sawmill and other stone structures. The loop concludes on a short section of the Godfrey Trail to connect to the Laurel Trail which you follow back to the trailhead.

Castle Craig

  • Location: Meriden, CT, in Hubbard Park, 24 miles southwest of Hartford
  • Length: 2.8-mile round-trip out-and-back
  • Difficulty Rating: Easy/intermediate
  • Best For: An adventurous excursion to a castle tower with a view
  • Dogs: Leashed

Conveniently located near downtown Meriden, Hubbard Park offers a unique landscape mixed with history, making it an engaging spot to hike and explore. Whether you are looking for a quick afternoon outing to enjoy the views, or a longer excursion to explore a section of the Metacomet Trail, Hubbard Park has a variety of options. The rocky promontories of the Hanging Hills, a range of ridges that are part of the longer Metacomet Ridge, give hikers unobstructed vantages of the surrounding area. The park’s rocky, wooded ridges are also ideal for hikers who seek a bit of elevation gain. Older, more adventurous kids can try the hike up, but for families with younger children, driving to the summit parking area of the tower is also an option.

The hike to Castle Craig and East Peak starts from the trailhead for the White Trail near Mirror Lake. There is also a large overflow parking lot near the lake if you don’t arrive at the trailhead early enough to secure one of the spots at the small trailhead lot. Start the hike on the White Trail, crossing Interstate 691 on a pedestrian bridge about half a mile into the hike. From here, you begin the climb up to East Peak. When the leaves are off the trees, you can catch a glimpse of the stone tower along the climb. The uphill is steep in places and a bit rocky in others, but the rewarding view from the ridge is worth the effort. Follow the White Spur Trail to the top of East Peak where you’ll find the 32-foot-tall stone tower of Castle Craig. You can climb an interior metal stairway to reach the top of this observation tower, which gives you a memorable vantage point of the greater Meriden area, including Sleeping Giant Mountain to the south and the Berkshire Mountains to the north. In the fall, the foliage provides a stunning backdrop and, on a clear day, you may even be able to spot New Haven and the waters of Long Island Sound.

Hemlock Hills

  • Location: Ridgefield, CT, 7 miles southwest of Danbury and 25 miles north of Stamford
  • Length: 2.3-mile round-trip loop
  • Difficulty Rating: Easy/intermediate
  • Best For: An easygoing hike with a backcountry feel
  • Dogs: Leashed

Hemlock Hills is a lovely trail system on a small tract of open space maintained by the town of Ridgefield. Located adjacent to Pine Mountain, Wooster Mountain State Park, Seth Low Pierrepont State Park and Bennett’s Pond State Park, the trails offer extensive acreage to explore. The Hemlock Hills trail system offers a little bit of everything, including several slightly more rugged, narrow trails that feel more remote than they actually are. The trails in the area wind up and down rolling hills, and there are trickling streams and creeks to cross in addition to some small lakes and marshy areas. In the spring and summer, keep an eye open for poison ivy and, after returning home, be sure to perform a thorough check for ticks.

This loop hike offers an introduction to the rocky and wooded trails that can be found in the area. Starting from the Lake Windwing parking area, hike past the iron gate on to the Red Trail which starts as a wide path. From here, you will use a short connector to hop on the mostly flat and wide Orange Access Trail – West. Turn right onto the Yellow Trail, which is one of the highlights of the loop. This narrow trail passes some impressive rock formations and interesting marshy areas before you turn onto the Blue Connector to access the Red Trail. This section of the Red Trail is gently undulating, and heads over and through large granite outcrops before descending alongside the stream that connects Rainbow Lake and Lake Windwing. From here, the trail widens and follows along the northern shore of Lake Windwing to finish the loop.

West Thompson Lake

  • Location: Thompson, CT, in the West Thompson Lake Recreation Area, 25 miles south of Worcester, MA, and 32 miles west of Providence, RI
  • Length: 7.2-mile round-trip loop
  • Difficulty Rating: Intermediate
  • Best For: A lakeside loop that makes a perfect weekend getaway
  • Dogs: Leashed

A visit to the West Thompson Lake Recreation Area offers a full day on the trails for adventurous hikers who will enjoy the mostly easy terrain circling both West Thompson Lake and the Quinebaug River. The recreation area provides a variety of outdoor activities including hiking, fishing, boating, kayaking or playing a round of disc golf. The West Thompson Lake Campground offers 24 sites to choose from if you would like to extend your stay. The shaded campground located close to the dam overlook promises a respite from the summer heat and waterfront views that are impressive at sunset.

The West Thompson Lake loop starts from the boat launch parking area off Reardon Road. From here, head south along the Shoreline Trail. The trail winds through the disc-golf course and crosses the dam, which provides a scenic view of the lake. Once on the west shore, the trail follows a wide dirt road that winds through meadows and woods near the water. You’ll come to an area where a bridge used to connect to the opposite shore. The remnants of the bridge are an ideal spot for a snack or lunch break. At the end of the Shoreline Trail, continue on the Quinebaug River Trail, which loops around the Quinebaug River. The trail can be a bit faint in spots, so keep an eye open for orange blazes to help you find your way. At about 6 miles, you will connect back to the Shoreline Trail which winds along the eastern shore of the lake and returns you to the boat launch.

Bear Mountain

  • Location: Salisbury, CT, in Mount Riga State Park, 51 miles northwest of Hartford
  • Length: 5.4-mile round-trip out-and-back
  • Difficulty Rating: Intermediate
  • Best For: Summiting the highest peak in Connecticut
  • Dogs: Leashed

Located near the region where Connecticut, New York and Massachusetts meet, Bear Mountain’s claim to fame as the highest peak in Connecticut comes with a small disclaimer. Though the summit of Bear Mountain, at 2,323 feet, is technically the highest peak in the state, it isn’t the highest point in the state. That accolade belongs to a 2,380-foot-high spot on the state line located on the southern slope of Mount Frissell, a peak in Massachusetts. Although a trek up Bear Mountain won’t allow you to reach the highest point in the state, this popular climb is still well worth the trip.

The hike starts in Mount Riga State Park from a large dirt parking lot at the eastern edge of the park. Start your hike on the Under Mountain Trail which climbs about 1,000 feet in just under 2 miles. The climb is mostly gradual with one steeper grade near the mile 1 mark, plus a few small streams to cross. From the end of the Under Mountain Trail, turn north onto the Appalachian Trail. Here, the hiking gets a bit more rugged as the trail climbs steeply along the ridgeline, and there are some rocky sections that require scrambling. You’ll know you have reached the summit when you come to a large, flat-topped rock pyramid that marks the peak. Climb this stone pyramid for some well-earned views! On a clear day and in winter when the trees have shed their leaves, this vista is particularly impressive, offering 360-degree views of the lakes and mountains of Connecticut, New York and Massachusetts. After savoring the view, simply retrace your steps back to the trailhead.

West Rock Ridge Loop

  • Location: New Haven, CT in West Rock Ridge State Park, 3 miles northwest of downtown New Haven
  • Length: 7.9-mile, round-trip loop
  • Difficulty Rating: Intermediate
  • Best For: A loop with equal parts easy trails and more rugged terrain
  • Dogs: Leashed

Located near downtown New Haven, Rock Ridge State Park offer a unique combination of views, rugged hiking, easy trails and other adventures such as fishing, mountain biking, horseback riding and boating. Whether you want to enjoy the scenic vistas found at the South Overlook and along the shores of Lake Wintergreen, or are on the hunt for a longer weekend outing to explore the ridges and valleys of West Rock Ridge, this park has a little something for everyone. A stop off at Judges Cave will even give you a tiny introduction to some basic spelunking for an interesting addition to your hike. This loop hits the highlights on the southern end of West Rock Ridge State Park with a stop by Judges Cave, a stroll along Lake Wintergreen, and a splendid vista at the South Overlook to start and finish your hike.

The loop starts on the Regicides Trail (Blue Trail), where you’ll encounter some of the more challenging terrain in the park. The trail follows the undulating ridgeline offering some rewarding views where there is a break in the trees. A short detour on the Green Trail to Judges Cave makes for a fun side trip. You can climb around the smooth rocks and tight crevices of this small cave, which is marked by a historic plaque. Continuing on the Regicides Trail, you will eventually turn on to the Purple Trail, a wooded connector leading to the wide and well-kept Red Trail. Continue south on the Red Trail along the eastern shore of Lake Wintergreen. The lake is most scenic in the summer and fall when the trees reflect in the still water of the lake. Be prepared to share this popular section of trail with other users on weekends and during peak season. Once past the lake, the trail continues south on gently rolling and wooded terrain. Save some energy for the end of the hike as the toughest climb is ahead! Near the 7.5-mile mark, the Red Trail turns west and climbs very steeply. The trail winds up the side of the ridge, gaining a little more than 100 feet in about a half a mile. This leg-burning climb will reward you as you return to the trailhead with views from the South Overlook where you can spot downtown New Haven, Sleeping Giant State Park, East Rock Park, Long Island and Long Island Sound on a clear day. Pack a post-hike picnic lunch to enjoy at the nearby pavilion.

Zoar Trail

    • Location: Oxford, CT, in Paugussett State Forest, 19 miles northwest of New Haven
    • Length: 6.4-mile round-trip loop
    • Difficulty Rating: Intermediate/difficult
    • Best For: A rugged loop for hikers looking for a more technical challenge
    • Dogs: Leashed

Located in Paugussett State Forest, the blue-blazed Zoar Trail offers a slightly more remote and secluded experience than some of the more well-known Connecticut public parks. A large parking area can be found at the southeastern corner of the loop at the end of Great Quarter Road. The Zoar Trail forms the outer loop of the trail system, and there are other connecting trails throughout. Although the trails are blazed and most of the junctions are marked, you may want to bring a map, as there are a few confusing intersections where a map will offer peace of mind that you are on the right track.

Hiking the loop clockwise allows you to tackle the steeper hills first, as you climb to the high point of the loop in a little more than 2 miles. For the most part, the ascent is steady with a few steeper sections and rocky portions where you will have to watch your footing. This section of the loop winds through the wooded western edge of Paugussett State Forest. There are a couple of small streams with waterfalls that you will cross. In the winter, these frozen cascades and iced-over streams add to the picturesque setting. Once past the high point of the loop, the trail descends—at times steeply—and you’ll want to watch your footing on the rocks. At just under four miles, you’ll navigate a steep downhill to the shore of Lake Zoar, a reservoir formed on the Housatonic River. In the warmer months, the lake is popular for boating, kayaking, fishing, tubing and waterskiing. In the colder months, the hike along the lake is quiet and scenic with the leaves off the trees. The lakeside section is mostly flat with a few small undulations. This is the most popular section of the loop, so you may encounter more foot traffic. As you reach the westernmost portion of the loop, there is one final steep hill before an easy hike back to the trailhead.

Rand’s View Out and Back

  • Location: Canaan, CT, near Great Falls Reservoir, 45 miles northwest of Hartford and 41 miles northeast of Poughkeepsie, NY
  • Length: 5.4-mile round-trip out-and-back
  • Difficulty Rating: Intermediate/difficult
  • Best For: A hike to one of the beautiful vistas along the Appalachian Trail
  • Dogs: Leashed

If you are looking for an excursion along the Appalachian Trail, this out-and-back hike provides a challenging route to a splendid view. The start of the hike is located near Great Falls Dam; taking some time to learn about the history of the area in addition to stopping by the dam for some photos is an added bonus if you have extra time. This scenic area along the Housatonic River offers a pleasant combination of rolling hills, wooded terrain and open meadows, where you will have expansive views of the area. The Appalachian Trail is clearly marked with signs and blue blazes.

From the trailhead, the hike starts with a steady climb on the Appalachian Trail. The climb gains nearly 800 feet in the course of two miles and heads through wooded terrain with a few open, grassy areas along the way. There are several steeper sections mixed in that will raise your heart rate and get your legs burning, but all of these climbs are fairly short and are followed by relatively mellow terrain where you can ease the pace and catch your breath. As the trail climbs to Mount Prospect, be aware that there are a few rocky ledges that can be slippery when wet or when covered by leaves or ice. Once you reach the summit of Mount Prospect, you will descend about 250 feet over about a mile before reaching a short trail that branches off to the open vista of Rand’s View. On a clear day, the views are absolutely stunning, and in the fall, the landscape is ablaze with the changing leaves—don’t forget to bring your camera. Pack a snack or lunch for a picnic at the viewpoint before retracing your steps to the trailhead.

Macedonia Ridge Trail

  • Location: Kent, CT, in Macedonia Brook State Park, 30 miles north of Danbury and 32 miles east of Poughkeepsie, NY
  • Length: 6.4-mile round-trip loop
  • Difficulty Rating: Intermediate/difficult
  • Best For: A tough hike to rewarding views from Cobble Mountain
  • Dogs: Leashed

Macedonia Brook State Park offers a trail system with a combination of rugged and technical terrain and easier, mellow hiking for those not looking for a summit adventure. The park also has a 51-site campground in a more rustic setting for visitors looking for a long weekend. The Macedonia Brook Campground offers reservable campsites and rustic cabins. In addition to hiking and camping, visitors can fish in the streams throughout the park. The southern trailhead to access this hike is located off Macedonia Brook Road. The pullout is not very large so you will want to arrive early during the busy summer months. As with any wooded hike in the state, be sure to check for ticks after your outing—especially if hiking with dogs and/or small children.

The Macedonia Ridge Trail is one of the highlights of the park. This trail has a rugged and challenging western portion and a more mellow eastern half. You can hike the loop in either direction; hiking it clockwise will allow you to tackle the tough terrain first. The western side of the loop heads north from the trailhead, climbing steadily and steeply toward Cobble Mountain. This viewpoint offers stunning views of the Catskills and Taconics. If you aren’t up for the full loop, an out-and-back to Cobble Mountain is an equally good option. For those continuing on, the Macedonia Ridge Trail heads north, climbing several other peaks and offering more open views interspersed with strenuous climbs. In the fall, this section of the hike is particularly pleasant as the colorful foliage adds to the beauty of the landscape. At the northern end of the loop, you will briefly skirt Hilltop Pond before the trail loops back to the south. The eastern portion of the loop has some hills but nothing as long or steep as what you’ve already tackled. Here, you will be hiking in the woods past numerous springs and streams, such as Macedonia Brook, as the trail winds south to return to the trailhead.