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Middlesex County, Connecticut

Looking for the best chillin in Middlesex County? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Middlesex County. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Middlesex County

  • Colchester, Connecticut

    Hike the Salmon River Trail, CT

    3.5
    7.4 mi / 770 ft gain
    There are many ways to do this trail (following the blue blaze and blue/red blaze for spur to waterfall): From the Day Pond (Google Day Pond in Colchester and there will be brown signs that will direct you towards the Day Pond Parking Lot when you get close,) Do the loop, 5.4 milesOut & Back ...
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  • East Haddam, Connecticut

    Explore Chapman Falls in Devil's Hopyard SP

    4.3
    If you map to Chapman Falls in East Haddam, CT, you will be brought to a parking lot opposite from the waterfall in Devil's Hopyard, a beautiful Connecticut state park. Once there, it's only a few minute walk down a very clear trail to the base of the 60 foot falls. There's plenty of room to set ...
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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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  • 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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  • 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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  • 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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  • Glastonbury, Connecticut

    Hike to Blackledge Falls

    3.8
    1.5 mi
    Although the park contains hiking trails, a pond and a streambelt, the primary draw of this parcel of land is the 25 foot waterfall. The falls flow varies depending on the volume of precipitation, from a trickle in the dry months to a three-pronged vertical drop after some consistent snow melt or...
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  • Meriden, Connecticut

    Chauncey Peak Loop

    5.0
    2.17 mi / 358 ft gain
    This loop follows the blue against the reservoir where it will break off to the left (this is a longer hike ~ 6.3 miles that'll eventually get to the peak), but if you're looking for this short hike, keep following the water side where it will meet the white trail for a short distance. Note: Som...
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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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  • Franklin, Connecticut

    Hike the Sprague Land Preserve Loop

    4.0
    3 mi
    The Sprague Land Preserve (also known as the Mukluk Preserve) was an incredible surprise. Whether it's hiking, fishing, or horseback riding it's a beautiful spot for anyone that can get there at sunrise and out before sunset when the gates close.You can easily get there by Google Mapping the name...
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  • Manchester, Connecticut

    Explore Wickham Park

    5.0
    Wickham Park Is open the first weekend in April and closes the last weekend in October. Entrances fees are $5 Monday-Friday and $7 Saturday-Sunday. The park is known for its 250 acres of  open fields, wildflowers, gardens, ponds and nature center. There is no where else can you go have a picnic w...
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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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  • 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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  • Groton, Connecticut

    Hike the Bluff Point Loop

    5.0
    3.6 mi / 164 ft gain
    Are you looking for a casual stroll in the woods? Want relax by the water with a beer in your hands? Or looking to do some SUP or kayaking? This Coastal Reserve and state park in Groton, Connecticut is worth the visit! A popular destination for the locals, families, and travelers. The trails are ...
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  • Ledyard, Connecticut

    Lantern Hill Loop

    4.0
    2.58 mi / 387 ft gain
    Lantern Hill in North Stonington, CT. has been one of my new favorite short hikes since I've been home for a long period of time. Interestingly enough, the trail I've noted is right next to the Foxwoods Casino. In fact, one of them is actually in the back parking lot of a resort. So plenty of pa...
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  • Chaplin, Connecticut

    Hike to Diana's Pool

    4.0
    1.3 mi / 45 ft gain
    The drive to Diana's Pool is worth it in an of itself, taking you through the backroads of Eastern Connecticut. To begin the hike just simply enter the woodland path and follow the trail. In order to go under the bridge just simply take the first left in the path and there will be a stream that f...
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