Connecticut's Top 10 Hiking Trails

Caves are a surprisingly regular feature along Connecticut’s trails, although they are apt to be recessed in jumbles of boulders or old mines rather than the elaborate cave systems you might find elsewhere. For example, a hike along the Tunxis Trail in Barkhamsted (4.4 miles out and back) will take you to the Indian Council Caves. 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: “After reaching an old woods road, a small staircase brings visitors into a deep evergreen forest, a peaceful oasis within the hardwood forest. Here the wind only 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.” And the very cool caves still await!

One of Connecticut’s most beautiful land trust properties is deep within Litchfield County at Steep Rock Preserve in Washington. There are many trails within this 974-acre natural wonder – for example, the Steep Rock Loop (4 miles) takes in many of the preserve’s features and Green Circle Trail (3 miles) follows the curves of the Shepaug River.

If you don’t mind a bit of scrambling, the Mattabesett Trail in central Connecticut offers marvelous views from atop the state’s famous traprock ridges. One of the great vistas comes after a climb up from Meriden’s Giufridda Park to Chauncey Peak and Lamentation Mountain. There’s a bit of a scramble to get up to elevation, but once there you’re walking along a ridge from which you can see Hartford to the north, almost to New Haven to the south, and seemingly unlimited views to the west. The descent brings you to a level walk along the lake before closing the loop. This up-and-down hike covers about 2 miles.

The wilds of northeast Connecticut are on ample display in Union’s Bigelow Hollow State Park, which in turn is located within Nipmuck State Forest. Here, trails head off in every direction, but hardy hikers will be interested in the portion of the Nipmuck Trail that runs from the park entrance, out and around Breakneck Pond, and then back again. The round trip is somewhere between 6 and 7 miles, featuring many water views, awesome rock formations, and all the sights and sounds of nature in Connecticut.

The southern trail head for the Mattatuck Trail is located in Wolcott’s Peterson Park, just off busy Route 69. Within minutes on the trail, however, the sounds of the outside world begin to fade, replaced by the babbling of the Mad River. Soon you will find yourself in a sort of natural amphitheater, or movie set, with towering hemlocks, filtered sunlight, tumbling and splashing water, and an understory of moss-covered boulders, ferns and mountain laurel. You may want to stay awhile, but if you stick with the trail for another 5 miles, crossing a couple of roads and even passing through a residential neighborhood, you’ll come eventually to Buttermilk Falls in Plymouth, one of Connecticut’s great secrets in the woods. For this 5.7-mile hike, you’ll have to park one car at the beginning and another at the end.

Rural Roxbury in Litchfield County 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. From the parking area, take a left onto the blue loop trail toward the Donkey Trail. 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 4-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 will tell you about all you’ve just seen.

Most of Connecticut’s state parks along Long Island Sound are big, but that is not so with Farm River State Park in East Haven. This is a smallish (62 acres) park that seems unpromising at first but that at length serves as a nice immersion into salt marshes and seaside sights and sounds. As for hiking, the trail lengths don’t amount to much, but you’ll like the places they take you. As the Department of Energy and Environmental Protection states: “Despite its size, the park’s diversity is remarkable. Snowy egrets feed in the marshland and share the tidal wetlands and rocky shore with a wide variety of ducks, gulls and the occasional blue heron.”

This 300-acre park is just a portion of the greater valley preservation effort that encompasses 758 acres in the towns of Easton and Weston. The walk-in park is accessible from north of the gate at Bradley Road in Weston and can be explored by following its dirt roads or cross country through valleys and over rugged hills. Look for wildlife, wetlands and watercourses. As of this past May, there are no dogs allowed and Bradley Road parking area is closed on weekends and parking is limited during the week. View the trail map here for additional parking.

In Litchfield, the 4,000-acre White Memorial Foundation has long held the flag high for nature and environmental awareness. There is camping here, as well as boating, picnicking, excellent birding, and 35 miles of hiking trails, including interpretive nature trails, a boardwalk trail that circles above a wetland habitat, and a good chunk of the Mattatuck Trail.

This park 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 blue-blazed Macedonia Ridge Trail. This 6.5-mile trail crosses Cobble Mountain (elevation 1,380 feet) and provides breathtaking views of Catskill and Taconic mountains. While hiking, visitors are surrounded by greenery and will encounter numerous springs and streams.

One of Connecticut’s most beautiful land trust properties is deep within Litchfield County at Steep Rock Preserve in Washington. There are many trails within this 974-acre natural wonder – for example, the Steep Rock Loop (4 miles) takes in many of the preserve’s features and Green Circle Trail (3 miles) follows the curves of the Shepaug River.