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Bridgeport, Connecticut

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

Top Chillin Spots in and near Bridgeport

  • Bridgeport, Connecticut

    Stroll around Fayerweather Island

    0.5 mi
    Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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  • Beacon Falls, Connecticut

    Hike the Spruce Brook Ravine

    4.0
    1 mi
    Working my way to the West side of the state, a friend recently helped me discover Naugatuck State Park in Naugatuck, CT. After driving up and around curvy roads, we entered the forest (with a lot of potholes). Here is a map of the park. The parking I am talking about here is the "P" symbol next ...
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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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  • Rye, New York

    Hike the Marshlands Conservancy Loop

    4.0
    1.55 mi / 125 ft gain
    Located along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...
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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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  • 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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  • 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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  • Patchogue, New York

    Camp at Fire Island's Watch Hill

    4.0
    2 mi
    If departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...
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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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  • 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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  • 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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  • Closter, New Jersey

    Hike Alpine White Trail (Stateline Lookout)

    5.0
    5 mi / -520 ft gain
    Starting at about 520 feet, the White path takes you along the Stateline Lookout which is a small stone building overlooking the Hudson River. The initial descent is your average hike through the woods and across a couple of wooden bridges until you reach the Giant Steps. The Giant Steps take you...
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  • Closter, New Jersey

    Hike to Huyler's Landing/ Closter Dock Loop

    4.0
    5.4 mi / 450 ft gain
    The easiest way to access this loop hike is by parking at the Palisades State Park Headquarters.  This is just off exit 2 from the Palisades Interstate Parkway.  Parking here is free and it is a short walk down a road to the Closter Dock Trail.  The Closter Dock Trail is more of a wide fire road ...
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  • Cold Spring, New York

    Photograph Indian Brook Falls

    2.8
    This is about as short a walk and as little effort as you can put in for a beautiful waterfall. You can barely call it a hike, but I'll list it as such since you do walk through the woods for 5 minutes. The trail is extremely well built, and is pretty easily accessible through the winter.The trai...
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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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