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Top 10 Hikes in Connecticut With the Best Views!

ByKristen Valenti Updated on

Ok friends, it’s about time I wrote this post. I’ve been writing about amazing hikes in Connecticut on my blog for years now but have yet to make a top 10 list.

I’ve written separate articles about the best sunrise hikes, sunset hikes, short hikes, waterfall trails, river trails, farm trails, and hikes with water views – all in Connecticut!

  • view from a hike in connecticut with rolling green hills and layers of trees and soft blue sky above.
  • woman crouching down with black dog at top of hike in connecticut with rolling green hills in background and blue sky above.

But this is the first time I’m sitting down top compile a very best hikes in CT list. That is – what are the best views in the state? The best all around trail experiences?

If you were to bring a friend from out of state and wanted to impress them with an amazing view, where should you bring them? Or if you’re visiting from out of state and you have to pick one hike – where do you go?

Those answers led me to make this list which was easy for me to put together considering I’ve grown up in Connecticut and have hiked here almost my whole life.

But I also wanted to keep it to a true “best of CT” list and keep it to 10 . So if I think another hike I must knock one off the list! Because while there are so many scenic and pretty trails worth walking in CT, I want the ultimate here.

Now most of these hikes are in the northwest part of Connecticut. That’s the area with the most elevation change and hills and mountains while the eastern part of CT is flatter.

So without further delay – let’s get to it! And be sure to come back and check out more posts about great hikes in Connecticut below:

10 Must-Do Hikes in Connecticut

Map of the hikes:

1. Rands View, Salisbury

wide open green meadow view with rolling hills int he distance and blue sky above with white fluffy clouds.
  • wide open green meadow view with rolling hills int he distance and blue sky above with white fluffy clouds.
  • wide open green meadow view with rolling hills int he distance and blue sky above with white fluffy clouds.
  • wide open green meadow view with rolling hills int he distance and blue sky above with white fluffy clouds.
  • 🥾Miles & Difficulty: 6 miles out & back, Moderate
  • 📈Elevation Gain: 1,200 ft
  • 🚙Parking: Google maps directions
  • 🌟Highlights: Views from Mount Prospect, views from Rand’s View
  • 🗺️ AllTrails Link 🔗

The hike to Rand’s View and the view there is one you won’t forget. One minute you’re walking along the Appalachian Trail and the next you see a little opening in the trees.

Getting closer and closer you see this whole panoramic view open up. Meadows, the hills of Bear and Everett in the distance, it’s like something out of The Sound of Music!

I also love the little view you get a couple miles in at Mount Prospect. It’s a gorgeous part of the state and great workout that feels satisfying but not too difficult with 1,200 feet of elevation gain spread over 6 miles.

I also like that this hike is easy to follow since you will be following the white blazes of the Appalachian Trail the whole time. Three miles in to an amazing wide open view, then turn around to head back to your car. A must-do Connecticut hike! 🥾

2. Pine Knob Lookout, Cornwall

green rolling mountains in summer at top of hike in cornwall ct
back of man in red fleece with green backback top of hike in connecticut with rolling green hills in the distance and housatonic river valley below and blue sky with fluffy white clouds above.
  • 🥾Miles & Difficulty: 2.6-mile loop, Moderate
  • 📈Elevation Gain: 770 ft
  • 🚙Parking: Google maps directions
  • 🌟Highlights: Two views, one big view facing southeast over Housatonic River Valley, plus Hatch Brook Falls 💦
  • 🗺️ AllTrails Link 🔗

The Pine Knob loop is a bit shorter at just 2.6 miles but it’s packed with scenery. It feels like you’re hiking through a magical park here.

You’ll start by hopping rocks across Hatch Brook then, taking the loop clockwise, you’ll walk up and along Hatch Brook Falls for about a mile. As you walk the gradual elevation the brook and falls are on your left.

Getting higher each pool of water or mini waterfall steals your attention from the trail. The dogs love splashing around here. Then, continuing on the loop you’ll encounter two different views out across the Housatonic River Valley.

A sea of rolling hills with the Housatonic River running through it, this is a top hike and view in CT!

3. Cobble Mountain, Kent

back of man sitting on top of hike with background baseball hat and rolling green hills and mountains in the distance behind him and soft blue sky with fluffy white clouds above.
  • view of green valley.
  • woman standing on cliff in connecticut with brown dog and green rolling hills in distance behind them and blue sky above.

If you’ve never been to Macedonia Brook State Park – you’re in for a treat! Driving through the winding country roads of Kent, you’ll pull down Macedonia Brook Road with the rolling Macedonia Brook running alongside you. It feels like you’re entering a dream land!

There are several different trails and routes you can take in this 2,300-acre state park. I included two different hikes above, one shorter and one longer loop. Both routes take you to the big view atop Cobble Mountain.

The views are epic and some of the best in Connecticut. You can see all the way to the Catskills on a clear day. The setting in this park makes the whole walk a scenic adventure. On top of the views, you’ll find stonewalls lining the paths, streams, mountain laurel, and a large pond. It’s one not to miss!

4. Bear Mountain, Salisbury

woman smiling in white tank top and green hiking shorts giving black dog a treat at top of bear mountain hike in connecticut with green mountains in the distance and blue sky above.
summit of bear mountain in connecticut in summer with green mountains and trees.

Bear Mountain is the tallest peak in Connecticut at 2,316 feet. It is a more difficult hike but the reward is saying you climbed CT’s tallest mountain 🙂 and also the beautiful views across the Taconic Mountains and into Massachusetts and New York.

At the summit, you’ll find a large stone cairn (pile of rocks) that has become Bear Mountain’s most recognizable landmarks. The cairn was built by hikers and marks the summit, making it a favorite spot for photos after the climb.

5. Lion’s Head, Salisbury

dramatic view of green valley with rolling green mountains in the distance from cliff in connecticut.
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  • woman standing on cliff top in white tank top next to brown dog looking out at view of rolling hills and a green valley on a summer day in Connecticut.
  • view of rolling hills and a green valley on a summer day in Connecticut.
  • 🥾Miles & Difficulty: 4.3 miles out & back, Moderate
  • 📈Elevation Gain: 1,154 ft
  • 🚙Parking: Google Maps directions
  • 🌟Highlights: Short scramble at the top leading to a cliff with wide open views
  • 🗺️ AllTrails Link 🔗

Lion’s Head is another of CT’s most rewarding hikes, offering incredible views for a relatively moderate climb.

Located in Salisbury along the Appalachian Trail, the summit features a dramatic rocky overlook with sweeping views of the Taconic Mountains, Twin Lakes, and the rolling hills of northwestern Connecticut.

There is a short scramble at the top where you will likely have to use your hands. But knowing the view is just yards from you it’s a small price to pay to make it to the top! If you’d like a shorter trail to Lion’s Head try this 2.3-mile route.

Or if you really want a challenge, you can combine Lion’s Head and Bear Mountain in this 8.5-mile route!

6. Meeker Trail at Macricostas Preserve, New Preston

View from Meeker Trail
  • black dog at the top of the meeker trail with red trees and overlooking lake waramaug
  • trail in litchfield county during fall with golden leaves
  • 🥾Miles & Difficulty: 4-mile loop, Moderate
  • 📈Elevation Gain: 708 ft
  • 🚙Parking: Google Maps directions
  • 🌟Highlights: Meadows, bridges, and view from Waramaug’s Rock facing west over Lake Waramaug
  • 🗺️ AllTrails Link 🔗

7. Caleb’s Peak via Fuller Pond, Kent

  • view of rolling hills and a green valley on a summer day in Connecticut.
  • brunette woman looking out from top of mountain with black dog next to her and rolling green hills and valley in the distance in summer with blue sky above.
  • view of rolling hills and a green valley from a hike in connecticut on a summer day in Connecticut.

I love how this hike starts at Fuller Pond in Kent. You walk along Fuller Pond which in itself is incredibly scenic.

You’ll then walk along Fuller Mountain Road and then right on Skiff Mountain Road. From there you’ll turn left and link up with the white-blazed Appalachian Trail which takes you to the must-see Caleb’s Peak view. This seemingly endless view stretches out across the Housatonic River Valley.

I’ve done this hike in every season and I never get tired of it seeing it emerge through the woods as your approach. After Caleb’s Peak you’ll cross Skiff Mountain Road again to link back up with the Fuller Pond Trail which will now take you left along the pond to the starting point.

8. Peoples State Forest Loop, Barkhamsted

brown dog on rocky cliff with rolling green hills in distance and pink and blue sky above at sunset time.
  • boardwalk running through green marshy area with pine trees in distance and blue sky with white clouds above.
  • view from hike in connecticut with river running through a green hilly valley.

9. Sleeping Giant State Park, Hamden

  • view from sleeping giant in connecticut looking over green stretch of land on a blue sky summer day.
  • a stone tower with multiple floors and rounded windows at sleeping giant state park with blue sky above.
view from a round winder at the top of sleeping giant tower in hamden with rolling green landscape in the distance and blue skies above.

If you live in Connecticut you’ve likely heard of Sleeping Giant. With over 32 miles of hiking trails, Sleeping Giant State Park is one of Connecticut’s premier hiking spots.

The park offers everything from easy walks to the iconic stone observation tower to challenging ridgeline hikes with rock scrambles, scenic overlooks, caves, and one of the state’s most extensive trail networks.

Since there are so many trails to take here I have a whole post dedicated to the top trails at Sleeping Giant. Check it out here ➡️ Top Trails at Sleeping Giant State Park 🌟 and choose the route for you!

10. Giuffrida Park, Meriden

sunset view from cliff with lake below and green rolling hlls in distance and orange golden sun in sky.
view from cliff in connecticut with green rolling hills in distance and framed with green leaves and trees in summer and blue sky above.
  • 🥾Miles & Difficulty: 4-mile loop, Moderate
  • 📈Elevation Gain: 764 ft
  • 🚙Parking: Google Maps directions
  • 🌟Highlights: Bradley Hubbard Reservoir, Lamentation Mountain, Chauncey Peak
  • 🗺️ AllTrails Link 🔗

Conclusion

So that’s it, friends. What do you think of this list – which hike are you planning first?

And what Connecticut hikes do you think deserve to be on here that I left off?! I’d love to hear your favorites!

Come back for more pretty hikes and walks in CT. There’s so much to explore in our beautiful state!

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