Top Hiking Trails in the Litchfield Hills Last Updated: March 2022

It’s hard to find a silver lining in the COVID-19 cloud; but if there is one, it’s that Connecticut residents, as well as out-of-state visitors young, old and in-between, have ventured into the great outdoors in search of fresh air and exercise as they take in our state’s rejuvenating natural wonders. Walkers, joggers, hikers, bikers – and their furry companions – have discovered the vast number of parks, forests, and trails in the Litchfield Hills (most of which are accessible at no charge and pet-friendly), with each one offering its own unique and memorable features. Whether you are a novice or seasoned hiker or nature lover, the Litchfield Hills has parks, preserves, and open spaces for everyone, with more than 367 miles of hiking trails. Here are some you might want to explore.

For a complete list, including pet-friendly and wheelchair-accessible parks and trails, click here.

Roxbury

Rural Roxbury has several 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. 

Wolcott

The southern trail head for The Mattatuck Trail is in Wolcott’s Peterson Park, just off busy Route 69. Within minutes of the trail, however, the sounds of the outside world begin to fade, replaced by the gentle 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. 

Litchfield

The 4000-acre White Memorial Foundation 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, an outdoor bird sanctuary, and a gift shop.

Looking for a quick afternoon adventure with a little history thrown in? The Ice House Ruins Loop at the White Memorial Foundation is a great way to...chill. This one-mile pathway is a nature lover’s dream, offering spectacular sights and loads of wildlife. Hike along Bantam Lake and discover the ruins of one of the largest ice harvesting operations in the country. There’s even an observation deck to take in the beauty of the lake below. Lefty on a leash is welcome too!

Established in 1968, the Litchfield Land Trust is one of Connecticut's earliest land trusts, dedicated to helping protect our area's scenic vistas, natural resources and the “New England character” of Litchfield for present and future residents. With more than 200 parcels comprising approximately 1,246 acres including the 340-acre Prospect Mountain Preserve, LLT welcomes visitors to enjoy hiking, fishing, cross-country skiing, snowshoeing, birding and photography. Of particular note is the 2020 extension of the Marsh Hawk Trail and the construction of a viewing platform into a vibrant wildlife habitat.

Kent

Beautiful Kent Falls State Park is an easy 6.7-mile out-and-back loop the whole family will enjoy, offering spectacular natural scenery, abundant wildflowers in season, and wildlife galore (great photo opps everywhere!), not to mention an up close and personal view of powerful and majestic Kent Falls, where you can feel the mist on your face as water cascades 250 feet down on its way to joining the Housatonic River

Macedonia Brook State Park (pictured above) 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 (elevation 1,380 feet) and provides breathtaking views of the Catskill and Taconic mountains. While hiking, visitors will encounter numerous babbling springs and streams.

Barkhamsted

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!

Washington

Steep Rock Association is a land trust whose mission is to conserve ecologically and historically significant landscapes in and around Washington and the Shepaug River Valley and to enhance the community’s connection with nature. Offering a wide variety of outdoor activities including hiking, horseback riding, fishing, camping, river recreation plus organized group events, Steep Rock is comprised of:

Hidden Valley Preserve in Washington Depot with 700 acres of mixed forest and meadows crisscrossed by nearly 17 miles of trails that offer a variety of hiking terrain. Wooded hillsides cascade into the River Valley below, creating breathtaking views from the Lookout and Pinnacle.

Macricostas Preserve, 400 acres offering an array of landscapes, as meadows and farm fields blend with wooded ridges and wetlands. Magnificent views, rare species of birds, and colorful stands of wildflowers make this an extraordinary destination.

Largest of the three, the 998-acre Steep Rock Preserve offers hiking trails that follow the river banks and provide access to great hiking trails. Explore the diverse flora and fauna along a flat trail on the river’s edge or climb through old-growth hemlock forests to summit views. There’s a hike for everyone within the 18-mile trail system located in the heart of Washington, including 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.

Ridgefield

Part of the Connecticut State Park System, Ridgefield’s Bennett’s Pond State Park, Hemlock Hills, Pine Mountain and Lake Windwing form one of the largest nature preserves in the southwest portion of the state. Glacial activity has left numerous erratic boulders and small cliffs throughout the area, offering a wide variety of terrain including meadows, woodlands, wetlands and steep ridges. The trip down to the pond is an easy and fast downhill hike; but heading north into Pine Mountain or further west into Hemlock Hills, the terrain can be challenging. Although a diamond in the rough, this is an awesome park to explore.

Norfolk

Home to a spectacular thundering waterfall, Campbell Falls State Park Reserve (pictured above) in Norfolk is a natural reserve offering hiking trails and stream fishing. Within the park, the Whitney River drops nearly 100 feet in a magnificent cascade through a tight gorge with the water flow changing twice, first to the left, then to the right, a rugged form not often found in New England. In early spring, its power is quite surprising, considering the gentle terrain of the trail and the surrounding forest.

Dennis Hill State Park in Norfolk is a 240-acre estate that was gifted to the State of Connecticut in 1935 by New York doctor, Frederick Shephard Dennis. An easy 1.8-mile hike up the Gazebo Loop Trail leads to the summit, where you will come upon a bungalow, formerly his summer home. At an elevation of 1,627 feet, you’ll take in breathtaking, panoramic views of the surrounding hills, and see all the way to New Hampshire on a clear day. Just what the doctor ordered!

New Hartford

It is said there is magic in New Hartford, at Jones Mountain Preserve. This 158-acre closed-canopy mountainside forest features mossy rocks, babbling brooks, old stone ruins and wildflowers that line one of the three trails on an old carriage road. You will be so mesmerized by this woodland paradise you might expect to stumble upon a hobbit or fairy during your journey. You can also bring your dog on and enjoy a perfect hike in this lesser-known preserve.

Torrington

You can really hit your stride with a hike through Burr Pond State Park in Torrington. This public recreation area covers 438 acres and is surrounded by 85-acre, man-made Burr Pond, which was created in 1851 as a source for power generation for a local tannery and three sawmills. One of the industrial buildings was used by Gail Borden as his first successful condensed milk factory. The building burned down in 1877, but a bronze tablet can be found on the hiking trails marking its location as well as Connecticut's role in the Civil War and the Industrial Revolution. Park is dog-friendly.

Salisbury

Not for beginners, the four-mile Lion’s Head Trail in Salisbury caters to very experienced adventurers; and if you can make it to the top, spectacular views of western Connecticut are your reward. The 1,738-foot peak is high enough that on a clear day you feel like you can see the entire state. So, lace up your hiking shoes, bring your dog on a leash and do some social climbing!

For all you hikers, bikers, bird watchers, rock climbers and outdoor enthusiasts, Mount Riga State Park (pictured above) in Salisbury is another not quite hidden Connecticut gem where you can get some exercise and enjoy nature at its best, with two trails rated as moderate (including the popular Bear Mountain Trail) and, for more experienced hikers, six trails rated as hard, ranging from 8.3 to 36.8 miles and from 692 to 2,608 feet above sea level. Check them out and you'll be out on the trail in no time!

Derby

If you’re into hiking and experiencing the wonders of nature (even in colder weather), visit historic Osbornedale State Park in Derby. And if you also happen to be a geology enthusiast, this outdoor haven has your name on it. Not only are there several different rock types showcased throughout the park; there are also geologic folds, quarries, and abandoned mines to explore. Most trails start and end in the main picnicking area and are color-coded. Also worth a stop is the wonderful Kellogg Environmental Center on the property.

Monroe/Newtown

Created from a section of an unused railroad corridor that runs from Monroe to Newtown, the Housatonic Railway Trail, a short 1.9-mile point-to-point trail is great for walking, running, hiking, biking and snowshoeing in a peaceful forest setting. Dog-friendly trail as long it’s on a leash.