12 Jaw-Dropping Hikes in Connecticut for All Levels
By Kay Rodriguez
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Updated June 24, 2021
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.
Easy Hikes in Connecticut
Kent Falls Loop
Location: Kent Falls State Park (Kent, CT)
TrailLength: 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
TrailLength: 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.
Location: Mine Hill Preserve (Roxbury, CT)
TrailLength: 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)
TrailLength: 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.
Silver Sands Loop
Location: Silver Sands State Park (Milford, CT)
TrailLength: 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)
TrailLength: 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.
Moderate & Difficult Hikes in Connecticut
Location: Salisbury, CT
TrailLength: 6.5 miles
Elevation Gain: 1,702 feet
Located in the Berkshire Mountains, Bear Mountain is a moderate summit trail that takes you to a scenic peak. 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
TrailLength: 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.
Location: Meriden, CT
TrailLength: 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…
Mattabesett Trail and Mount Higby
Location: Meriden, CT
TrailLength: 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.
Sleeping Giant Head Trail (Blue and Violet Loop)
Location: Sleeping Giant State Park
TrailLength: 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
Breathable hiking clothes – For warmer hikes, you’ll want to wear a sweat-wicking shirt and breathable pants, like these Patagonia hiking shorts for men and women. For cold-weather hikes, we recommend dressing in layers, including merino wool baselayers for men and women, a down puffer jacket for men and women, and a Northface waterproof outer shell for men and women (a must for hiking in Seattle). And don’t forget a pair of the best women’s and men’s hiking socks!
Trekking poles – You won’t need these for every single hike, but we suggest throwing them in your car just in case. We recommend the Black Diamond Trail Ergo cork trekking poles, which are lightweight, easy to transport, and durable.
Water bottle – Having water available at all times is a huge must. To limit disposable plastic, we recommend bringing your own refillable water bottle. We’re obsessed with Hydro Flask water bottles because they keep water cold for hours.
Sunscreen and bug spray – Sweatproof sunscreen and DEET bug spray can help you avoid sunburn and bug bites, two of hiking’s most annoying after-effects. Our favorite kind of sunscreen is Sun Bum, as it is free of harsh chemicals and safe for marine life, including coral reefs.
A brimmed hat or cap – The sun can be brutal in open hikes, so always pack a brimmed hat or capfor 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 the Osprey Tempest 20 or the Talon 22 day packs because they’re comfortable and breathable for long hikes. For more information, check out our best day packs for any terrain guide.
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