Best fun hikes in Connecticut

Trails picked for the payoff — ridgelines, ravines, and loops that beat the crowded state-park defaults.

Fun Hikes

Leatherman's Cave & Black Rock

Rock shelter on the Mattatuck Trail once used by the legendary Leatherman, reached from Black Rock State Park in Watertown. Ledgy climb…

Fun Hikes

Chatfield Hollow

Killingworth state park built around a spring-fed swimming pond, a covered bridge, and ledge trails with caves to poke around. Nice mix of…

Fun Hikes

Huntington State Park

Former estate turned park in Redding with easy woodland loops around several ponds and bronze sculptures at the main gate. Flat, wide…

Fun Hikes · Griswold

Pachaug State Forest

Connecticut's largest state forest at over 24,000 acres in Voluntown. Multiple ponds for swimming and paddling, including Beach Pond on the…

Fun Hikes · East Haddam

Eightmile River Preserve

One of the few federally designated wild and scenic rivers in New England, running through Salem and East Haddam. Crystal clear water, good…

Fun Hikes · Lebanon

Salmon River State Forest

The Salmon River in Colchester runs cold and clear through a wide state forest with some of the best fly fishing in the state — it's a…

Fun Hikes · Union

Bigelow Hollow State Park

A wild and remote-feeling state park in Union, CT's least-populated town. Otter Pond and Bigelow Pond are connected by trails through…

Fun Hikes · Naugatuck

Whittemore Glen State Park

An underused state park in Naugatuck with a deep ravine trail that follows a rushing brook through hemlock gorges with small falls and…

Fun Hikes · Sharon

Pine Knob Loop

A short loop in the Housatonic State Forest above Cornwall that climbs to a rocky outcrop with views of the Housatonic River valley and the…

Fun Hikes · New Milford

Hidden Valley Preserve

A Nature Conservancy preserve in New Milford with a wild river gorge cut by the Still River. The trail drops into a ravine with mossy walls…

Fun Hikes · Cornwall

Steep Rock Preserve

One of CT's best-kept secrets — a river gorge in Washington where the Shepaug River cuts through steep wooded cliffs. The trails follow the…

Fun Hikes · Roxbury

Judd's Bridge Area

A scenic stretch of the Housatonic River in Bridgewater where the river narrows through a rocky gorge with good swimming and fishing. An…

Fun Hikes · Weston

Devil's Den Preserve

The Nature Conservancy's largest preserve in New England, in Weston. Over 20 miles of trails through rocky forests full of glacial…

Fun Hikes · Tolland

Shenipsit State Forest

A large state forest straddling Stafford, Ellington, and Tolland with a long ridge trail running through it. Multiple access points, fire…

Fun Hikes · Manchester

Case Mountain

A popular hiking and mountain biking destination in Manchester with multiple trails through a forested preserve, reaching rocky ledges with…

Fun Hikes · Lyme

Oswegatchie Hills Nature Preserve

A 200-acre coastal forest preserve in East Haddam with trails along the Eight Mile River and rocky outcrops overlooking CT River tidal…

Fun Hikes · Southington

Cedar Mountain Preserve

A compact but rewarding trail loop in Plainville on the Metacomet Ridge, reaching open ledge views north and south along the traprock…

Fun Hikes · Sharon

Sharon Land Trust – Mudge Pond Trails

A quiet network of land trust trails in Sharon around Mudge Pond, with views of the pond and the surrounding hills. The Sharon Land Trust…

Fun Hikes · North Canaan

Canaan Mountain

A high plateau in Canaan topped with a rare pitch pine-scrub oak barren ecosystem. The trails take you through this unusual landscape that…

Fun Hikes · Goshen

Mount Bushnell

A quiet peak in Sharon with views of the Housatonic Valley and New York's Taconic Range. Not well-known compared to nearby Lion's Head, so…

Fun Hikes · Trumbull

Aspetuck Falls

A 20-foot waterfall in Easton on the Aspetuck River, accessible from a small pull-off on Sport Hill Road. Locals swim here in summer but it…

Fun Hikes · Norwich

Yantic Falls

Right in the city of Norwich, this 30-foot waterfall drops into a gorge in the middle of an urban park. The surrounding Native American…

Fun Hikes · Colchester

Day Pond Waterfall

Day Pond State Park in Colchester has a small but pretty waterfall feeding into the pond, surrounded by a network of easy hiking trails.…

Fun Hikes · Haddam

Cockaponset State Forest

CT's second largest state forest with miles of blue-blazed trails through hemlock ravines and rocky ridges. The Pataconk Lake area is…

Fun Hikes · Hebron

Gay City State Park

A ghost town swallowed by forest, with ruins of a 19th-century mill community scattered along the trails. Swimming pond in summer, great…

Fun Hikes · East Hampton

Hurd State Park

Rugged terrain along the Connecticut River with rocky bluffs and hidden coves. The trail system is lightly traveled and genuinely…

Fun Hikes · Barkhamsted

Peoples State Forest

Towering white pines and hardwoods along the West Branch Farmington River. The Agnes Bowen Trail gives excellent river views. Very quiet on…

Fun Hikes · Meriden

Chauncey Peak — Lamentation Mountain

A traprock ridgeline hike in Meriden starting from Giuffrida Park. Summit views from Chauncey Peak and Lamentation Mountain span from…

Fun Hikes · Groton

Bluff Point Coastal Reserve

Connecticut's only undeveloped coastal reserve, an 800-acre peninsula in Groton jutting into the Thames River and Fisher's Island Sound.…

Fun Hikes · Hamden

Sleeping Giant State Park

A Hamden classic. The ridgeline trail follows the profile of the "sleeping giant" and leads to a four-story stone observation tower at the…

Fun Hikes · Canaan

Bear Mountain

The highest peak in Connecticut at 2,316 feet, located in Salisbury near the Massachusetts and New York borders. The 6.5-mile round trip…