12 Jaw-Dropping Hikes in Connecticut for All Levels - Urban Outdoors
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While Connecticut may not seem like a hiker’s dream state, there are certainly some amazing hidden gems here that will surprise and delight even the most experienced hikers. With rocky summits, beautiful forests, serene waterways, and picturesque fall foliage, Connecticut has a wide variety of stunning nature areas to explore. We created this guide to the best hikes in Connecticut so that you can explore some of the state’s most beautiful parks, trails, and landscapes! Make no mistake, no matter what experience or ability level you are, you’ll definitely be able to find a place for hiking in Connecticut that suits your fancy.

Photo Credit: the SkyHum (Flickr CC)

Easy Hikes in Connecticut

Kent Falls Loop

  • Location: Kent Falls State Park (Kent, CT)
  • Trail Length: 0.7 miles
  • Elevation Gain: 232 feet

Perfect for families, dogs, and hikers of all levels, the short, 0.7-mile Kent Falls Loop trail will take you to one of the most scenic waterfalls in Connecticut. With a 250-foot waterfall that’s perfect for photography, this trail offers several viewpoints to view this spectacular cascade. Most reviewers say that this hike is extremely easy, making it perfect for anyone looking for fabulous views on a scenic but short trail. Go during the spring after snowmelt for the most powerful waterfall flows!

Bluff Point Coastal Reserve Trail

  • Location: Groton, CT
  • Trail Length: 3.6 miles miles
  • Elevation Gain: 170 feet

If you’re looking for seaside views on an easy, accessible waterfront trail, the Bluff Point Coastal Reserve Trail is one of the best hikes in Connecticut to enjoy the water. One of the nicest things about this easy trail is that it’s got well-maintained, wide trails, perfect for all levels of hikers and for social distancing. You’ll experience a variety of landscapes, from rocky shorelines to forests to marshy flatlands. Visitors say these trails can get busy, so we’d strongly recommend going in the early morning to catch sunrise on the water and avoid the main crowds that tend to arrive later in the day.

Photo Credit: Christopher Burns (Flickr CC)

Roxbury Mines

  • Location: Mine Hill Preserve (Roxbury, CT)
  • Trail Length: 3.6 miles
  • Elevation Gain: 511 feet

For history lovers and hikers alike, the Roxbury Mines Trail in Mine Hill Preserve is a wonderful place to go hiking in Connecticut. With several beautiful historic mining structures to explore, forested areas to walk through, and many rock formations to admire, this easy trail is perfect for a weekend adventure in the wilderness.

Fern-lined trails take hikers 3.6 miles through the shady forest canopy, which brings you to the Mine Hill ironmaking complex, a historic ironworks facility in the forest. While not in use today, you can catch a glimpse of the ovens and furnaces used to create iron pieces from iron ore, the next step after mining the ore. Not only is this a wonderful way to get outdoors, but it’s one of the coolest historic hikes in Connecticut as well!

Steep Rock Yellow Circle Trail

  • Location: Steep Rock Preserve (Washington Depot, CT)
  • Trail Length: 4.2 miles
  • Elevation Gain: 521 feet

There are few places for hiking in Connecticut that have the variety and natural beauty of the Steep Rock Circle trail. Located in Steep Rock Preserve, this 4.2-mile trail is home to tons of wildlife, breathtaking suspension bridges, pristine waterways, and more. This easy trail is the perfect place to go on a leisurely hike with your dog or with kids, as there’s so much to see and do along the dirt paths.

With so many scenic areas, it’s no wonder this trail gets quite busy on weekends and holidays. We’d recommend going early in the morning to secure a parking space and enjoy the trails with fewer crowds.

Photo Credit: jpellgen (Flickr CC)

Silver Sands Loop

  • Location: Silver Sands State Park (Milford, CT)
  • Trail Length: 2.1 miles
  • Elevation Gain: Minimal

The second beach hike on our list is the Silver Sands Loop, which is located near Milford, CT. For peaceful waterfront views along a boulder-filled shoreline, the Silver Sands Loop trail is one of the best hikes in Connecticut. If you head here in the early hours of the morning, you can take this beginner- and family-friendly hike and watch the beautiful sunrise glistening over the water. On the trail, you’ll find locals on their daily strolls or walking their dogs, and you can walk all the way to Walnut Beach along the shoreline.

Mashapaug Pond Loop

  • Location: Bigelow Hollow State Park (Union, CT)
  • Trail Length: 5.2 miles
  • Elevation Gain: 639 feet

Located near the border of Massachusetts, the Mashapaug Pond Loop is one of the most beautiful hikes in Connecticut for enjoying serene lake views and spotting fall foliage. Situated in the middle of Bigelow Hollow State Park, this trail feels like a complete escape from civilization. With thick, forested trails that border the shoreline of this very picturesque lake, this trail offers a little bit of challenge for beginner hikers, as it’s slightly hilly and has quite a bite of terrain variety.

Don’t rush through the trail! Along the way, there are several picnic areas that you can rest at or pull out some snacks and enjoy the scenery – we’d recommend the Mashapaug Cove picnic area for some of the most beautiful views.

Photo Credit: Morrow Long (Flickr CC)

Moderate & Difficult Hikes in Connecticut

Bear Mountain

  • Location: Salisbury, CT
  • Trail Length: 6.5 miles
  • Elevation Gain: 1,702 feet

Located in the Berkshire Mountains, Bear Mountain is a moderate summit trail that takes you to the highest point in Connecticut. As part of the Appalachian Trail, this path is one of the more frequented, longer hikes in Connecticut, and for good reason – the rocks on the top of the mountain offer lovely views of the surrounding mountains, especially in the fall when these tree-covered peaks begin to change colors.

Bear Mountain is situated in the area surrounding Salisbury, CT, which is one of the more topographically challenging areas for hiking in Connecticut. Here, you can find hikes of moderate and even strenuous difficulty that even the most experienced hikers will enjoy. If you’re looking to do a hiking weekend getaway, this is a fantastic area to visit!

Mt. Tom Tower Loop

  • Location: Litchfield, CT
  • Trail Length: 1.5 miles
  • Elevation Gain: 400 feet

If you’re into historic hikes in Connecticut, the Mt. Tom Tower Loop won’t disappoint. Situated in the middle of Mt. Tom State Park is a summit trail with a castle-like tower at its peak. A moderately difficult 1.5-mile trail will take you to the top of this summit, where you can climb the tower and catch views of the Long Island Sound, as well as the surrounding mountains and forests. Especially great for families or sunset/sunrise hikers, the views from the top are quite beautiful, especially in the fall as the leaves change colors.

The trail is steep in certain sections, but it’s definitely doable for hikers of all levels willing to take on a bit of an uphill challenge! Plus, it’s a short trail, so the steep ascent doesn’t last long.

Photo Credit: John Cudworth (Flickr CC)

Castle Craig

  • Location: Meriden, CT
  • Trail Length: 4.4 miles
  • Elevation Gain: 797 feet

With scenery that looks like something out of Game of Thrones, the Castle Craig Loop (Mirror Lake, Castle Craig, Merimere Reservoir Loop) is one of the most scenic places for hiking in Connecticut. Just look at the photos! With rocky scrambles and some significantly steep uphill areas, this trail offers a moderate challenge for hikers looking for a bit more variety in their terrain.

Along the way, you’ll pass by Mirror Lake, an absolutely stunning, still lake that has gorgeous fall foliage. The rustic-looking Castle Craig was gifted by Walter Hubbard, a manufacturing businessman who was the namesake of Hubbard Park. Once you arrive at the castle, you can take the stairs to the observation deck at the top, which offers breathtaking views of Hubbard Park and the surrounding nature areas.

Mount Prospect & Rand’s View

  • Location: Canaan, CT
  • Trail Length: 6.3 miles
  • Elevation Gain: 1,305 feet

Hailed by some as one of the best views along the Appalachian Trail, the stunning Rand’s View trail is one you can’t miss if you’re looking for picturesque hikes in Connecticut. As a moderately difficult hike, this trail is accessible to most hikers willing to take on a challenge and some rock-filled trails. The rewards are obvious: stunning views, beautiful forests, and the opportunity to hike through one of the most iconic sections of the Appalachian Trail in the state of Connecticut. Not bad for a half-day hike, we’d say…

Photo Credit: Doug McGrady (Flickr CC)

Mattabesett Trail and Mount Higby

  • Location: Meriden, CT
  • Trail Length: 8.9 miles
  • Elevation Gain: 1,719 feet

One of the longer and more fun trails on this list is the Mattabesett Trail to Mount Higby. This mountain trail offers stunning views throughout the entire trail as it climbs along a ridge to Mount Higby. As one of the longest trails on our list, it’s a great option for those looking for a longer day hike in the mountains with some more serious elevation gain – over 1,700 feet! This trail is especially beautiful in the fall, when you can see the leaves changing colors for miles and miles on clear days. You’ll also catch glimpses of the nearby mountainsides as you scramble around the rocky terrain. It’s beautiful, it’s fun, it’s challenging…and it combines all of the best things about hiking in Connecticut in one 8.9-mile stretch.

Photo Credit: GPA Photo Archive (Flickr CC)

Sleeping Giant Head Trail (Blue and Violet Loop)

  • Location: Sleeping Giant State Park
  • Trail Length: 8 miles
  • Elevation Gain: 1,692 feet

Perhaps the coolest and most challenging trail on our list, the Sleeping Giant Head Trail is one to remember. You’ll scramble up scenic (but challenging!) rock formations over the course of nearly 1,700 feet of elevation gain to reach the summit of this mountain in the scenic Sleeping Giant State Park. Aside from having the coolest name ever, this park boasts absolutely breathtaking views of southwestern Connecticut, especially in the fall when the leaves change. What avid hikers like the most about this trail is that it’s a really good workout, with several scrambling areas and a very steep, leg burning uphill that makes the views at the top even more rewarding.

Additional Resources for Hiking in Connecticut

What to Bring

  • Hiking boots – You can’t hike without appropriate footwear, period. For most trails, we recommend an all-purpose waterproof boot with ankle support. We recommend Salomon hiking boots or Keen hiking boots for a comfortable hike.
  • Breathable hiking clothes – For warmer hikes, you’ll want to stay cool in a sweat-wicking shirt/tank top and breathable pants, like these PrAna hiking pants for men and women. For cold-weather hikes, we recommend dressing in layers, including merino wool baselayers, an insulated puffer jacket, and a waterproof outer shell. And don’t forget a pair of the best hiking socks in the world!
  • Trekking poles – You won’t need these for every single hike, but we recommend throwing them in your car anyway just in case. We recommend the Black Diamond foldable trekking poles, which are lightweight and easy to transport.
  • Water bottle – Having water available at all times is a huge must. To spare disposable plastic, we recommend bringing your own refillable water bottle. We’re obsessed with Hydro Flask bottles because they keep water cold for hours, but a good old Nalgene works very well too.
  • Sunscreen and bug spray – This should be self-explanatory, but sweatproof sunscreen and DEET bug spray can help you avoid sunburn and bug bites, two of hiking’s most annoying after-effects.
  • A brimmed hat or cap – The sun can be brutal in open hikes, so always pack a brimmed hat or cap for day hikes in the sunshine.
  • Emergency blanket and first aid kit – We’d strongly recommend bringing a first aid kit and a lightweight emergency blanket on every hike. Why? Because the unfathomable can happen, and it’s always best to play it safe.
  • Durable day pack – A durable day pack is the perfect spot to stash all your hiking gear. While any backpack will do, we recommend Osprey day packs because they’re comfortable and breathable for long hikes.

Wondering what exactly you should pack for your next hike? Visit our Complete Day Hiking Packing List for our full list and our top gear recommendations.

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Kay Rodriguez is the Chicago-based travel writer and photographer behind Jetfarer and Skyline Adventurer. When she's not blogging furiously on her laptop or editing photos, you can find Kay running, hiking, or paddling in a new city.

2 Comments

  1. Avatar

    Kay,

    I haven’t been back east yet (I’m in AZ) but I plan to some day because I have a goal to hike in each state. I don’t see much on Connecticut so thank you for posting this!! Saved for sure. 🙂

    ~Allie

    • Avatar

      That’s an incredible goal! So excited for you to explore Connecticut. It’s got some beautiful and seriously underrated hikes.

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