Top Hiking Trails in the Litchfield Hills Last Updated: December 2020

Connecticut is crisscrossed by hundreds of miles of hiking trails, with many of the best in the Litchfield Hills. These trails run through high land and low, across difficult and easy terrain, and they offer unique insight into the history, geology, flora and fauna of the area. They also serve as blissful and relaxing getaways from the stressors of daily life. So, before it gets TOO cold, take a hike!

As a reminder, be sure to check Connecticut DEEP’s twitter channel and website before venturing out for the most up-to-date safety guidelines for outdoor recreation and information about state park closures.


Rural Roxbury has a number of natural preserves that are great for hiking, but among the most interesting is the Mine Hill Preserve that runs past old iron mines, granite quarries and the ruins of a 19th-century iron-making complex. You’ll pass a reservoir, two mine tunnels and a series of grated air shafts, which now serve as entryways to several bat populations. The four-mile trail continues past massive granite cliffs, eventually descending back to the Shepaug River Valley, past an abandoned quarry and finally to the furnace complex, where excellent signage explains the history of everything you’ve just seen.


The southern trail head for the Mattatuck Trail is located in Wolcott’s Peterson Park, just off Route 69. Within minutes of the trail, the sounds of the outside world begin to fade, replaced by the babbling of the Mad River. Soon you will find yourself in a natural amphitheater – amidst towering hemlocks, filtered sunlight, tumbling and splashing water and an understory of moss-covered boulders, ferns and mountain laurel. If you are adventurous enough to stay on the trail for another five miles, you’ll cross several roads, pass a residential neighborhood and eventually arrive in Buttermilk Falls in Plymouth, one of Connecticut’s great woodland secrets. For this 5.7-mile hike, you’ll have to park one car at the beginning and another at the end.


The 4000-acre White Memorial Conservation Center in Litchfield has long held the flag high for natural splendor and environmental awareness, where you can camp, boat, picnic, enjoy excellent birding, and hike 35 miles of trails, including interpretive nature trails, a boardwalk trail that circles a wetland habitat, and a good chunk of the Mattatuck Trail. The Conservation Center features special displays, hands-on exhibits, live animals, outdoor bird sanctuary and a gift shop.


Macedonia Brook State Park in Kent extends 2,300 acres and crosses over mountains and peaks, giving visitors an opportunity to enjoy various levels of hiking and trekking. One of the most popular trails includes the 6.5-mile blue-blazed Macedonia Ridge Trail, which crosses Cobble Mountain (elev. 1,380 feet) and provides breathtaking views of the Catskill and Taconic mountains. While hiking, visitors will encounter numerous babbling springs and streams.


A hike along the Tunxis Trail in Barkhamsted (4.4 miles out and back) will take you to Indian Council Caves, where you make your way into the woods from busy Route 219 and embark on “a magical romp,” according to Peter Marteka of the Hartford Courant. He goes on to say, “After reaching an old woods road, a small staircase brings visitors into a deep evergreen forest, a peaceful oasis among the hardwood trees. Here the wind sways the tops of the trees high above as pine needles float down like snowflakes. It’s one of those delightful places where you are totally enveloped into the natural world.” Sounds sublime, doesn’t it? And the elaborate cave system still awaits!


One of Connecticut’s most spectacular land trust properties is deep within Litchfield County at Steep Rock in Washington, where many trails await eager hikers within this 974-acre natural wonder. Just a few are the four-mile Steep Rock Loop, which showcases many of the preserve’s wondrous features; and the three-mile Green Circle Trail that follows the snaking curves of the Shepaug River.

A real hidden gem is Hidden Valley Preserve with 700 acres of mixed forest and meadows crisscrossed by nearly 17 miles of trails that offer a variety of terrain for hiking. Wooded hillsides cascade into the river valley below, creating breathtaking views from the Lookout and Pinnacle.