Climbing & Hiking Trails - 17 min read

20 Best Hiking Trails in Connecticut (For Ocean & Mountain Views)

Alex Frick

Alex Frick, Updated September 24, 2022

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Connecticut is an eclectic mix of rural countryside and ocean splendor in southeast New England. Rated as one of the best states to live in the country, it is no surprise that Connecticut is rich in adventure and beauty.

With towering mountains outside colonial towns and incredible views from the shores of the Atlantic Ocean, this state offers limitless adventures throughout the land. Connecticut is a state with remarkable hiking journeys for miles, trekking through some of the country’s most prestigious countryside.

Your Guide For The Best Hiking Trails in Connecticut

1. Bear Mountain Trail


Directions:
From North Canaan, head west on US-44 W and drive for 5.9 miles. Take a right onto Cobble Road and continue for 0.4 miles. Turn right onto CT-41 N and drive for another 2.7 miles and turn left into the Undermountain Parking Area, the trailhead for this hike.

The hike to Bear Mountain leads ambitious travelers to the highest peak (2,316 feet) in all of Connecticut – but not the highest point.

Interestingly enough, the southern slope of Mount Frissell in Massachusetts crosses state lines into Connecticut and stands at 2,380 feet.

The rigorous climb passes through dense woodlands before reaching a challenging rock scramble. Once completing the scramble, you will reach the flattened-rock peak overlooking the stunning landscape for as far as the eye can see.

Difficulty: Moderate
Distance: 6.1 Miles
Elevation Gain: 1,683 Feet

2. Ragged Mountain Blue and Red Blazed Loop


Directions:
From Berlin, head northeast on CT-9 N and drive for 1.7 miles and use the left two lanes to merge onto CT-9 N. Drive for 0.3 miles and take exit 24 for CT-71. Continue for 0.3 miles and merge left onto CT-571 W, and drive for another 1.1 miles. Turn left onto CT-71A S and drive for 1.2 miles and make a right onto West Lane. After 0.6 miles, the parking area will be on your right.

Ragged Mountain is a steep mountain in central Connecticut known for its daring vertical cliff faces. To reach the top, you will take the combined loop along the Red Blaze and Blue Blaze Trail.

The mild climb follows the ridge consisting of exposed rock – increasing your scenic views the higher you ascend.

As you approach the summit, the trail will enter the woodlands on a comfortable and level pathway. Look to the sharp-angled cliff faces, this trail is well-known in rock climbing circles.

Difficulty: Moderate
Distance: 5.6 Miles
Elevation Gain: 843 Feet

3. Sleeping Giant Tower Trail


Directions:
From New Haven, head north on I-91 N for 13.1 miles and take exit 10 toward CT-40 N. Continue on CT-40 N for 3.0 miles and use the right two lanes to merge onto CT-10 N and drive for another 1.4 miles. Make a right onto Mount Carmel Avenue and drive for 0.5 miles then take a left, followed by an immediate left, and the parking area for this hike will be on your right.

The Sleeping Giant Tower Trail is a charming introduction to Sleeping Giant State Park. This scenic hike is not your average walk.

This trail begins as a typical smooth dirt trail before twisting up relentless switchbacks, scrambling over fields of boulders, before reaching the summit.

From the top of the hill, several overlooks are allowing panoramic views in all directions. Be sure to stop by the castle – an architecturally beautiful stone tower just off the Light Blue Trail.

Difficulty: Easy
Distance: 3.1 Miles
Elevation Gain: 597 Feet

4. Wadsworth Falls Loop


Directions:
From Hartford, head south on I-91 S for 14.2 miles and take exit 20 for Middle Street. After 0.2 miles, turn left onto Middle Street and make an immediate left onto Country Club Road. Drive for 1.1 miles and make a right onto Higby Road and continue for 1.2 miles.

Turn left at the second cross street onto CT-66 E and drive for 1.3 miles before turning right onto George Street. Continue for 0.6 miles and turn left onto Middlefield Street and drive for another 0.3 miles. Turn right onto Forest Street and after 0.6 miles, the parking area will be on your right.

The Wadsworth Falls Loop is a family-friendly hike for adventurers of all skill levels. The trail is made of compact and comfortable gravel and is a steady climb until you reach the highlight of this journey, Wadsworth Falls.

Wadsworth Falls is a wide and powerfully cascading waterfall from the rushing current of the Coginchaug River. With the wide pathway, this trail is popular with hikers, mountain bikers, and equestrians.

Unfortunately, if you intended to take a swim beneath the falls, you are out of luck. Swimming is prohibited.

Difficulty: Easy
Distance: 3.6 Miles
Elevation Gain: 364 Feet

5. Chauncy Peak Trail


Directions:
From Hartford, head south on I-91 S for 14.2 miles and take exit 20 for Middle Street. After 0.2 miles, turn left onto Middle Street and make an immediate right onto Country Club Road. Continue for 1.7 miles and merge onto Westfield Road and drive for another 0.7 miles. After 0.1 miles, turn right into Doctor Francis Giuffrida Park at the parking area for this hike will be on your right.

The Chauncey Peak Trail is a wonderful opportunity for hikers to experience the expansive views of this gorgeous mountain peak. Unlike the typical mountain trail, this hike is short but sweet. Although brief, these views must be earned.

The hike follows a series of steep and strenuous switchbacks along the ridge of the mountain before reaching the summit.

Once reaching the peak, you will be rewarded with several different panoramic views overlooking the dense, forested woodlands and a stunningly beautiful reservoir.

Difficulty: Moderate
Distance: 2.2 Miles
Elevation Gain: 351 Feet

6. Bluff Point State Park and Coastal Reserve Trail


Directions:
From New London, head east on I-95 N for 4.0 miles and take exit 88 for CT-117. After 0.2 miles, turn right onto CT-177 S and continue for 1.0 miles. Turn right onto Fort Hill Road and drive for 0.3 miles. Turn left on Depot Road and after 0.7 miles, the parking area for this hike will be on your left.

The Bluff Point State Park and Coastal Reserve Trail is a comfortable hike leading to Connecticut’s picturesque coastline.

The trail is well-maintained and wide, making it extremely popular for trail runners and cyclists. The hike is shaded by the canopy of the local fauna and leads to the feature attraction of the trail, Bluff Point.

Bluff Point is a trail made of boulders of varied shapes and sizes that extend out into the depths of the Block Island Sound. The bluff is a popular place for fishing, with anglers eager to hook the elusive winter flounder or snapper bluefish.

Difficulty: Easy
Distance: 3.6 Miles
Elevation Gain: 154 Feet

7. Mirror Lake, Castle Craig, and Merimere Reservoir Loop


Directions:
From Middletown, head west on CT-66 W for 4.4 miles and merge onto I-691 W. Drive for 1.5 miles and take exit 7 toward downtown. Merge onto State Street and continue for 0.6 miles before turning right onto E Main Street. Stay on E Main Street for 1.8 miles and turn right onto Hubbard Park Drive. After 0.2 miles, turn left onto Mirror Lake Drive. Continue for 0.1 miles and turn right and the parking area will be on your left.

The Mirror Lake, Castle Craig, and Merimere Reservoir Loop is a stunning hike, rich with history and diversity. Beginning along the shores of reflective Mirror Lake, this trail takes you to the overlooking cliffs of Castle Craig, a towering stone lookout constructed in the early 1900s.

Castle Craig holds the distinction of being the highest point within 25 miles of the coast from Florida to Maine. Down the slope of the hill is the picturesque Merimere Reservoir, a body of water that features a quaint forested island.

Difficulty: Moderate
Distance: 4.4 Miles
Elevation Gain: 797 Feet

8. Talcott Mountain Yellow Trail

Credit: Brian Bisaillon / Flickr


Directions:
From Hartford, head northwest on Albany Avenue for 2.1 miles and turn right onto CT-189 N. Drive for 0.8 miles and slight left CT-185 W and continue for another 4.8 miles. Take a left onto Summit Ridge Drive and after 0.3 miles, the parking area will be on your left.

The hike along the Yellow Trail to the summit of Tower Mountain is a moderate adventure that will surely leave you in awe. The beginning of the trail is very steep before leveling off.

Soon you will approach the peak – home to the grandest views of Connecticut from the observation room of Hueblein Tower.

Hueblein Tower has tremendous panoramic views of the Connecticut River Valley to the east and of Farmington Valley to the west. Witnessing the fall colors is always a defining event in Connecticut, but the views from the tower as the leaves change are unrivaled.

Difficulty: Moderate
Distance: 2.5 Miles
Elevation Gain: 423 Feet

9. Zoar Trail

Credit: Wikipedia


Directions:
From New Haven, head northwest on Derby Avenue for 8.0 miles and use the left two lanes to turn left onto Main Street. After 0.5 miles and merge onto CT-34 W and drive for 8.1 miles. Turn right onto Great Quarter Road and after 1.3 miles, you will reach the parking area.

The Zoar Trail is a challenging journey that is not for the faint of heart. This hike in the Paugussett State Forest has expansive views in all directions, but that is not what this trail is best known for.

While only seven miles, the extremely hilly loop has sections with high grades of elevation gain and is technically difficult.

The hills are more like ascending fields of tall boulders. If you are fond of relentless rock scrambles, the Zoar Trail is up for the challenge.

Difficulty: Moderate
Distance: 7.0 Miles
Elevation Gain: 1,072 Feet

10. Roxbury Mines Trail


Directions:
From New Milford, head southeast on CT-67 E for 5.9 miles and make a left toward Mine Hill Road, followed by an immediate slight left to stay on Mine Hill Road. After 0.3 miles, the parking area for this hike will be on your right.

The Roxbury Mines Trail is a journey to the ruins of an abandoned granite, iron, and quartz mine built in the 1860s. The hike leads you past the historic remains of stone structures used for mining before shutting down in 1875.

While you are unable enter the mines, it is interesting to know that there are miles of tunnels that lay just beneath your feet.

Within the dark stone structures are excellent opportunities to explore and identify distinct types of mushrooms and fungi that inhabit this damp and lightless atmosphere.

Difficulty: Moderate
Distance: 3.6 Miles
Elevation Gain: 511 Feet

11. Salmon River Trail Loop from Comstock Bridge


Directions:
From Middletown, head east on CT-66 E for 5.9 miles and turn right onto CT-16 E. Continue on CT-16 E for 5.2 miles and turn left onto Comstock Bridge Road and the parking area for this hike will be on your right.

The Salmon River Trail is an enjoyable journey through both Salmon River State Park and Day Pond State Park. The hike leads into the dense woodlands with trees with great diversity.

Relax on the shores of the wildlife-abundant Salmon River before reaching one of Connecticut’s greatest features, the historic Comstock Bridge.

Comstock Bridge is a picturesque white covered bridge. Built in 1883, it is the only bridge of its kind in all eastern Connecticut. In 1974, Comstock Bridge was listed on the National Register of Historic Places.

Difficulty: Moderate
Distance: 6.5 Miles
Elevation Gain: 925 Feet

12. Mianus Maze Trail


Directions:
From Stamford, head west on Broad Street for 1.2 miles and turn left onto Palmer Hill Road, followed by an immediate right onto Westover Road. Drive for 1.9 miles and make a slight right onto Merriebrook Lane. Continue for 0.2 miles and the parking area will be on your right.

The Mianus Maze Trail is a technical mountain biking trail in the protected areas of Mianus River State Park. The maze refers to the complicated network of trails that commonly get mountain bikers turned around and disoriented.

The nature hike is interpretive, with twelve different signage posts serving as educational guides of the surrounding ecosystem.

The trail winds and wanders through dense woodlands under canopies that are the ideal habitat for endangered bald eagles.

Difficulty: Moderate
Distance: 4.9 Miles
Elevation Gain: 321 Feet

13. Sleeping Giant Head Blue and Violet Loop Trail

Credit: Elise Jolie / AllTrails


Directions:
Make a right onto Mount Carmel Avenue and drive for 0.5 miles and the parking area for this hike will be on your left.

The Sleeping Giant Head Blue and Violet Loop Trail is arguably the most rewarding hike in Sleeping Giant State Park, but also the most challenging. The trail is an arduous climb up the ridge of standalone Sleeping Giant Mountain, also known as Elk Mountain.

Commonly known as the most difficult hike in Connecticut, the trail wanders through rough and rocky terrain before ascending high-grade rock scrambles. The trail ultimately leads to astonishing views from atop this majestic summit.

Difficulty: Strenuous
Distance: 8.0 Miles
Elevation Gain: 1,692 Feet

14. Rattlesnake Mountain via Metacomet Trail

Credit: Sage Ross / Flickr


Directions:
From Hartford, head southwest on I-84 for 7.7 miles and take exit 38 for US-6 W. After 0.3 miles, turn left onto US-6 W and continue for another 2.1 miles and the parking area will be on your left.

The hike along Metacomet Trail to Rattlesnake Mountain is a difficult hike that offers beautiful views of the surrounding valleys but has a secret at the summit – a dark cave with a tale.

In the 1800s, explorer Will Warren was chased out of Farmington for his anti-religious views and retreated to the peak of Rattlesnake Mountain before finding this cave.

Legend has it, he used the cave to hide from the townspeople and called the boulder cave his home. In 1870, a body was found in the cave and is rumored to be Will Warren himself.

Difficulty: Moderate
Distance: 2.5 Miles
Elevation Gain: 396 Feet

15. Yellow Circle Blazes Loop


Directions:
From New Milford, head northeast on CT-109 E for 5.7 miles and turn right onto Cook Street. Drive for 0.4 miles and turn right onto River Road. Continue for 1.2 miles and turn left onto Tunnel Road followed by an immediate left and the parking area will be on your left.

This hike in the Steep Rock Preserve wanders along diverse terrain before reaching a stunning view from a sharp cliff overlook.

The Yellow Circle Blazes Loop is a comfortable and level trail that takes you through lush flora and fauna in native Connecticut.

While there is some elevation gain reaching the summit, most of the journey follows the tranquil shores of the Shepaug River. The trail is smooth and wide, perfect for adventurers of all skill levels.

Difficulty: Moderate
Distance: 3.7 Miles
Elevation Gain: 423 Feet

16. Pine Knob Loop via Appalachian Trail

Credit: Morrow Long / Flickr


Directions:
From New Canaan, head south on US-7 S, and drive for 15.4 miles and the parking area for this hike will be on your right.

The Pine Knob Loop via the Appalachian Trail is an easily accessible trail that brings you to the summit of not one, but two mountain summits. The hike is a peaceful trek through dense forests with plenty of shade.

There are some steeper sections, but the effort is well worth the reward. From the summit of the sister peaks, you will have earned unparalleled views of the Housatonic River and its expansive valley.

Difficulty: Moderate
Distance: 2.5 Miles
Elevation Gain: 770 Feet

17. Vista and Devil’s Oven via Orange Trail Loop

Credit: Susan S. / Flickr


Directions:
From Colchester, head south on CT-16 W for 0.8 miles and turn left onto Bulkeley Hill Road. Drive for 2.4 miles and merge onto O’Connell Road Extension and continue for another 1.0 miles. Merge onto Ackley Cemetery Road and drive for 0.9 miles and turn left onto Early Road.

Continue for 0.8 miles and make a right onto Haywardville Road. Drive for 0.3 miles and turn left onto State Highway 434 and continue for 0.9 miles and the parking area will be on your left.

The hike up the short but steep Orange Trail to Devil’s Oven and Vista leads to a unique set of mountaintop features that will leave you in awe.

You will climb a remarkable 464 feet in just over a mile, but once you reach the summit, you will be rewarded with just ridiculous views from the scenic vista.

In addition to the grand overlook, there is a small and bizarre cave system tucked away in a tall rock wall. The cave is delicate and unsafe. You should not enter under any circumstances.

Difficulty: Moderate
Distance: 2.2 Miles
Elevation Gain: 462 Feet

18. Mount Lamentation Loop

Credit: Wikipedia


Directions:
From Hartford, head south on I-91 S for 14.2 miles and take exit 20 for Middle Street. After 0.2 miles, turn left onto Middle Street and make an immediate right onto Country Club Road.

Continue for 1.7 miles and merge onto Westfield Road and drive for another 0.7 miles. After 0.1 miles, turn right into Doctor Francis Giuffrida Park at the parking area for this hike will be on your right.

The trek to the peak of Mount Lamentation is a shorter mountain hike with tremendously tall rock faces. The hike follows the ridge of the picturesque mountain. Some locals have said that this ridge is the most scenic traprock ridge walk in the state.

These remarkable cliff faces can reach heights of 550 feet tall! Once you complete the beautiful climb, enjoy the expansive views from Mount Lamentation’s many vista points.

Difficulty: Moderate
Distance: 3.5 Miles
Elevation Gain: 474 Feet

19. Mount Frissell and Brace Mountain Loop Trail

Credit: Peter DeGennaro / Flickr


Directions:
From Salisbury, head north on CT-41 N for 4.8 miles into Massachusetts and merge onto MA-41 N. Drive for 7.8 miles and mark a sharp left onto Mount Washington Road. Continue for 4.4 miles and turn left onto East Street. Drive for another 6.2 miles and the parking area will be on your right.

The Mount Frissell and Brace Mountain Loop Trail is notable because it is not limited to only Connecticut. The loop wraps around the northern ridge of Mount Frissel towards Brace Mountain in New York State.

The trail will then return south after exploring the ridge of the mountain and will reconnect with Mount Frissell in Massachusetts. Once you navigate the ridge on the eastern edge of the mountain, you will return to the steep edge of Mount Frissell in Connecticut, the tallest point in the state.

Difficulty: Moderate
Distance: 5.0 Miles
Elevation Gain: 1,059 Feet

20. Case Mountain Trail

Credit: Jen Tringone / AllTrails


Directions:
From Hartford, head east on I-84 E for 3.8 miles and take exit 59 for I-384 E toward Providence. Drive for 5.5 miles and take exit 4 toward Highland Street and after 0.4 miles, turn right onto Wyllys Street. Continue for 0.2 miles and the parking area for this trail will be on your right.

The Case Mountain Trail is a popular hiking and mountain biking trail that leads to unobstructed views from its photo-worthy vista point.

The climb up this majestic mountain can be strenuous at times. However, once you reach the peak, you will be rewarded with expansive views of the entire Connecticut River Valley and fantastic views of the Hartford city skyline.

If you don’t mind the crowds, try to summit the mountain in the late afternoon hours. The sunset from this vantage point is truly memorable.

Difficulty: Moderate
Distance: 6.1 Miles
Elevation Gain: 803 Feet

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