Cheshire, Connecticut

Top Spots in and near Cheshire

  • Cheshire, Connecticut

    Hike to Roaring Brook Falls

    1.2 mi / 377 ft gain
    Arriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...
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  • Meriden, Connecticut

    Hike the Metacomet, Blue, and Yellow Loop

    5.0
    4.5 mi / 976 ft gain
    Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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  • Hamden, Connecticut

    Hike the Tower Trail to the Blue Trail at Sleeping Giant SP

    5.0
    3 mi / 518 ft gain
    Sleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...
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  • Hamden, Connecticut

    Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP

    5.0
    3 mi / 518 ft gain
    Since I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...
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  • Hamden, Connecticut

    Boulder & Free Climb off the Blue Trail In Sleeping Giant SP

    Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...
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  • Meriden, Connecticut

    Higby Mountain Trail

    2.11 mi / 486 ft gain
    The popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice!  The beginning of the hike is mostly flatter land and an incline w...
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  • Southington, Connecticut

    Rock Climb Ragged Mountain

    The main face of Ragged Mountain (elev. 761 feet) is home to a lot climbing in central Connecticut. It runs north-south for about 600 feet. Its max height of 100 feet. The crag is home to several rock climbing guides and schools. Routes range in difficultly from great for the beginner (5.3) to su...
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  • Hamden, Connecticut

    Mountain Bike West Rock Ridge State Park

    West Rock Ridge State Park is a 700 ft high scenic ridge that is located on the west side of New Haven. There are tons of good mountain biking trails located all around the ridge that can satisfy all types of skill levels. The easiest place to park is the Lake Wintergreen parking lot, which sits ...
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  • Berlin, Connecticut

    Hike the Ragged Mountain Memorial Preserve

    4.5
    5.5 mi / 560 ft gain
    Ragged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds.  The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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  • Middletown, Connecticut

    Explore Wadsworth Falls

    5.0
    0.25 mi
    When it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...
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  • Litchfield, Connecticut

    Photograph Daffodils at Laurel Ridge

    Laurel Ridge is a private owned Farm , the owners are generous enough to let people visit these flowers so please be respectful of there rules.  You may see the Daffodils from Sunrise-Sunset and usually fully bloomed Early April-May. Laurel Ridge is the perfect way to start Spring, the smell and ...
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  • Middlesex County, Connecticut

    Hike to Glen Falls

    5.0
    0.75 mi
    Accessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...
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  • Glastonbury, Connecticut

    Hike the Cotton Hollow Nature Preserve

    5.0
    3 mi
    There are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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Camping and Lodging in Cheshire

Hop Brook Lake Recreation Area
Naugatuck, Connecticut

Hop Brook Lake Recreation Area

Northfield Brook Lake Group Shelters
Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Postcard Cabins Machimoodus
Moodus, Connecticut

Postcard Cabins Machimoodus

From $190 / night

Niantic / I-95 Exit 72 KOA Journey
East Lyme, Connecticut

Niantic / I-95 Exit 72 KOA Journey

Guides, Insights and Stories from Cheshire

Earth Day 2020 Goes Online: How to Get Involved

Earth Day 2020 Goes Online: How to Get Involved

Jonathan Stull