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Newtown, Connecticut

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

Top Hiking Spots in and near Newtown

  • Dover Plains, New York

    Hike Dover's Stone Church

    4.5
    Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...
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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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  • Hopewell Junction, New York

    Lake Canopus Viewpoint

    4.0
    2.07 mi / 148 ft gain
    Its a great place to explore as it has a beautiful calm lake especially in the fall, the reflection of the water and the awesome colors are unbelievable. Its a short hike but you certainly could go further up. Parking is free by the road, hike towards the lake about a mile or so. The sound of bi...
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  • Hopewell Junction, New York

    Beaver Pond via Appalachian Trail

    5.0
    3 mi / 400 ft gain
    Beaver Pond is a small body of water created by a dam that was constructed during the days of iron ore mining in the area.  The pond is crystal clear and has a wonderful tree line right on the water.  The best time to visit here is early morning in the fall.  With the leaves changing color they m...
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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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  • Cold Spring, New York

    Hike the Perkins/Fahnestock/Charcoal Burners Trail Loop

    7.5 mi / 800 ft gain
    This is one of my favorite hikes in the Clarence Fahnestock State Park. A real mixed bag but mostly very enjoyable. The trail starts at the Charcoal Burners Trailhead Route 301. There is only road side parking on a soft shoulder, both sides of the road.  After a short walk into the forest, you re...
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  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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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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  • 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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  • 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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  • Beacon, New York

    Hudson Highlands Overlook Trail

    3.29 mi / 1017 ft gain
    Hudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.
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  • Beacon, New York

    Hike Fishkill Ridge

    Fishkill Ridge is a strenuous but rewarding hike, and one of the less known areas in the Hudson Valley. The parking area is at the very end of Sunnyside Road in Beacon, along with the information board at the trailhead. The red trail leaves the lot and will take you up to the first peak on the ri...
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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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  • Briarcliff Manor, New York

    Hike Kate Kennard Trail

    1.8 mi / 140 ft gain
    If you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...
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  • Philipstown, New York

    Hike the Osborn Loop

    7.6 mi / 850 ft gain
    The Osborn Loop trail itself is not a loop.  It connects to a 2.5 mile section of the Appalachian Trail.  Hiking these together creates the loop.  Start at the trail head for the Appalachian Trail on South Mountain Pass Road.  There is parking for two or three cars.  Walk up the road a short dist...
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  • Cold Spring, New York

    Hike the Washburn/Nelsonville/Undercliff Loop

    7.2 mi / 2000 ft gain
    This is a difficult loop hike that has several different starting points.  I chose to start at the Washburn Trail Head, which is the lowest starting point you can select.  Nearly on the Hudson River, the trail ascends immediately along a well maintained road designated by white disc markers.  Aft...
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