For the 50+ Traveler

Connecticut is one of the most naturally beautiful states in the country. Blessed with a diversity of terrain, Connecticut has flat meadows, rolling hills, mountains, valleys, rivers, lakes, and even a taste of the Atlantic Ocean by way of the Long Island Sound. It’s a hiker’s paradise for those who enjoy a visual feast along with their footsteps. Here are our recommendations for nine beautiful hikes in Connecticut.

A trail through Mianus River Park in Connecticut.

1. Mianus River Park


This is our pick for the best hike in Connecticut. Check out TravelAwaits’ picks for the best hikes in all 50 states here. If you’re looking for a spot with diverse landscapes and plenty of things to see and do, then Mianus River Park is the place for you. A nature reserve on the Greenwich/Stamford border, Mianus River Park has over 390 acres, including two miles of river flowing through the park. The park also offers dense forest lands, varied terrain, lots of birds and wildlife for viewing, and miles of trails, making this a great place for hiking as well as other outdoor activities. The hiking trails are not challenging. The 4.5-mile Yellow Loop that goes around the park and the 2.5-mile Nature Trail, which has 13 different points of interest marked along the way, are both easy hikes to enjoy. You’ll get beautiful scenery any time of year, but for the best photos, check out the gorgeous fall foliage and glistening winter snowscapes.

Spaulding Pond in Norwich's Mohegan Park.

2. Mohegan Park


Mohegan Park is another beautiful spot great for easy hiking and outdoor activities. There’s a special Veterans Memorial Rose Garden with 2,500 rose bushes, so if you’re a flower lover, you’ll want to plan a visit in June when blossoms are at their peak. The Mohegan Park Loop is almost two miles long and offers wide trails to enjoy all year. Leaf peepers will enjoy the New England fall color on display. The forested trail, while easy, offers many sites, including wooden footbridges crossing over creeks, interesting rock formations, and ponds that offer peaceful scenery. Several trails intersect, so you can choose a different path at a few points along your route. All are well-marked. Wildlife lovers may spy white-tailed deer. Although not far from civilization, Mohegan Park feels like a perfect getaway for an easy and peaceful hiking experience.

The summit of Bear Mountain in Salisbury, Connecticut.

3. Bear Mountain, Mount Riga State Park


Bear Mountain is located in Mount Riga State Park at the Connecticut, New York, and Massachusetts state lines. The best-known feature of Bear Mountain is that at 2,316 feet, it’s the highest peak in Connecticut (though not the highest point). This is an intermediate hike that starts out with a gradual climb on the Under Mountain Trail, rising about 1,000 feet. You’ll find beautiful scenery with some waterfalls and small streams for crossing along the way. Your hike gets a little steeper after the first mile, with some slightly more challenging rocky sections and ledges. At the summit, there’s a large pyramid of rock with a flat top marking the peak. If you climb to the top, you’ll be rewarded with amazing views of lakes and mountains in all three states. If you go in winter, when many trees have lost their leaves, the view will be even more spectacular. The round trip is almost six miles and follows a section of the famous Appalachian Trail.

Chapman Falls in Devils Hopyard State Park.

4. Devils Hopyard

East Haddam

Don’t be scared by the name. Devils Hopyard State Park in East Haddam is 860 acres full of wonders worth exploring. A waterfall and terrific views join a couple of unusual features that early settlers attributed to their villainous namesake. Choose from six different trails offering options for hikers of all levels. The Red Trail, which is just under three miles long, takes you through forests and past waterfalls. Fans of waterfalls will love Chapman Falls, which has a drop of over 60 feet where Hopyard and Foxtown Roads meet. The Orange Vista Loop is quite popular, beginning at a covered bridge and offering a beautiful view from the Vista Cliff Overlook. A short, steep side trail will take you to the Devils Oven, a small cave that recedes into the rock. Cylindrical pools carved into a ledge (that seem unnaturally perfect) are another of the park’s “devilish” features. Regardless of how the striking anomalies came to be, you’ll certainly enjoy the unique pleasures of hiking in the Devils Hopyard.

Castle Craig in Meriden's Hubbard Park.

5. Hubbard Park


Not too many places offer a short hike to a tower. But Hubbard Park does. It’s also home to some pretty dandy hiking and other wonderful features to enjoy. Castle Craig is a stone observation tower that looks like a medieval castle. A quick and easy three-mile round trip will get you from parking to the castle and back. But there’s much more to see on the 1,800 acres of parkland that are open all year. For something more challenging, try the Metacomet Trail. The Meriden segment of this New England National Scenic Trail is rugged but dazzling. Overall, there are 16 miles of trails, ranging from easy to difficult, to explore in the park. If you want some time in here before or after hiking, you’ll find woodlands, lakes, streams, flower gardens, and picnic areas designed with the help of Frederick Law Olmsted, who designed New York City’s Central Park. The vehicle road to Castle Craig is open from May through October, but you can hike to it anytime, and the fall colors are hard to beat.

The covered wooden bridge in Southford Falls State Park.

6. Southford Falls


If you’re looking for a hidden gem, Southford Falls State Park on the Oxford-Southbury border is one of the best-kept secrets in Connecticut. Here you’ll discover 169 acres of nature’s bounty. Hike the Red Trail, which goes for just under two miles around the entire park. You’ll pass a covered wooden bridge, flowing streams, and several scenic falls. The trail is well marked, but you’ll need to pay attention because there are deer paths and shortcuts made by locals that can set you off walking through the woods. There’s also an old observation tower offering a lovely view of the area below. Winter is a great time to visit for hiking and also ice skating, sledding, and cross-country skiing in the sparkling snow.

The Sleeping Giant Tower in Hamden, Connecticut.

7. Sleeping Giant State Park


When you don’t know exactly what kind of hike you feel like, head to Sleeping Giant State Park, where 23 different trails offer something for every hiking mood and skill level. A memorable hike is the Sleeping Giant Tower Trail with its spectacular views. The trail is just two miles long, and the final view is breathtaking. Sleeping Giant gets its name from the mountaintop that resembles, well, a sleeping giant. Summer is a good time to hike here thanks to easy gravel trails, fantastic birdwatching opportunities, and wildflowers in bloom. The observation tower at the top of Mount Carmel gives you a fantastic view. As beautiful as this hike is, it can get busy in daytime. Try early morning or late afternoon for less company, or opt for one of the 22 other trails to enjoy more solitude. All of the trails are well marked with colored blazes so you know where you are and can keep heading where you want to go.

The Connecticut coastline in Bluff Point State Park.

8. Coastal Reserve Trail, Bluff Point State Park


The Coastal Reserve Trail in the 800 acres of Bluff Point State Park is a three-and-a-half-mile loop with amazingly diverse scenery. You’ll pass lush greenery and pretty little wildflowers during the warmer months. As a special treat, you’ll walk by the coastline. The trail is flat and has only a small incline, making it perfect for ambling in the warm summer months. Take your swimsuit with you and hike about a mile to the beach, where you’ll be able to ditch the crowds. If you love the shore in winter, snowscapes surrounding the water will wow you with their beauty. Go around dawn or dusk when the lighting is breathtaking. The peninsula is wooded and juts out into Long Island Sound, making quite a spectacular sight. The trail is a relatively easy hike, even when there’s snow. Wear appropriate gear for the time of year you’re hiking, especially to enjoy the romantic sight of a beautiful winter coastline beside a woody forest.

Views of the Housatonic River in Housatonic Meadows State Park.

9. Pine Knob Loop Trail, Housatonic Meadows State Park


Pine Knob Loop Trail in Housatonic Meadows State Park and Housatonic State Forest on the west side of the Housatonic River is a challenging two-and-a-half-mile loop trail. You’ll hike through thick, cozy woods and take in beautiful views of the river valley, lush greenery, and lovely wildflowers. Wildlife and bird enthusiasts may glimpse big birds like vultures and hawks in this wooded wonderland. The Pine Knob Loop Trail also takes you onto a portion of the Connecticut Appalachian Trail. Some spots become a little more rugged, but the majority of hikers should be able to manage just fine. The area includes a wide range of ter­rain so be sure to have boots with good, gripping soles. Toward the end of the hike, you’ll see Hatch Brook, with its flowing, cascading waterfalls for an unforgettable finish.

Pro Tips

While hiking in Connecticut is wonderful all year, if you’re not opposed to going out during winter, you will find some of the most spectacular scenery and fewer crowds. Also be on the lookout for birds and wildlife wherever you roam. It’s not unusual to see deer, wild turkeys, and other woodland creatures enjoying the natural bounty around them.

This article is presented by Keen Footwear. For our hikes, we wore KEEN’s Terradora II Waterproof Boots and Targhee III Waterproof Mid boot. They were light and great for all kinds of terrain. They supported our feet well on rocky hikes and were totally waterproof. Shop KEEN’s Terradora, Targhee, and other hiking shoes here.