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Washington, Connecticut

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

Top Hiking Spots in and near Washington

  • Beacon, New York

    Sunset Point - South Beacon Mountain Loop

    4.0
    8.92 mi / 2470 ft gain
    This loop hike form the Notch Trail northern trailhead on Route 9D.  There is enough parking at this trailhead for about 5-6 cars.  The Notch Trail is identified with blue trail markers.  It is well maintained and plenty of markers to guide your way.  This is important because there are m...
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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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  • Cornwall, New York

    Storm King Mountain Loop

    4.5
    2.44 mi / 400 ft gain
    This is an easy, yet very rewarding hike with a lot of viewpoints on the way up. Technically you scale up two mountains, Butter Hill and Storm King, but most people just describe it as Storm King Mountain. This is a great hike for families with younger kids, those who don't have much time but wan...
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  • Cornwall, New York

    Hike the North Point Loop

    6.5 mi / 1400 ft gain
    There is three different trailheads to access the North Point Loop.  I chose the trailhead that would give me the longest hike.  That would be the Butter Hill parking area on Route 9W north.  From the parking lot, start on the connector trail designated with white markers.  Follow this for about ...
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  • Cornwall-on-Hudson, New York

    Hike the Stillman - Bluebird Loop

    5.4 mi / 1200 ft gain
    This loop hike starts at the northern trailhead of the park where the Stillman Trail begins.  The parking area has enough space for only 6 or 7 cars.  Start off on a wide maintained carriage road.  After about a half mile, the Stillman Trail (yellow markers) breaks of to the left.  However, stay ...
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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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  • 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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  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    5.0
    9.29 mi / 981 ft gain
    Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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  • Cortlandt, New York

    Hike the Camp Smith Trail

    4.5
    5.92 mi / 1759 ft gain
    This approximately 3-hour hike borders the Hudson River, and is one of the best in Westchester County. Start off at the parking area at the Bear Mountain Tollhouse, or at a small parking area farther up Bear Mountain Road, if you want a slightly shorter hike. The trail is fairly steep in places, ...
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  • Philipstown, New York

    Anthony's Nose via Appalachian Trail

    4.6
    1.95 mi / 682 ft gain
    Parking for the trail runs along both sides of 9D right up until the Bear Mountain Bridge. It can be busy on the weekends so just make sure you're as far off the road as you can and be especially careful unloading kids and dogs. The trailhead is located at approximately 41.322571, -73.975949 and ...
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  • Bear Mountain, New York

    Hike Bald Mountain, Bear Mountain State Park

    4.7
    6.8 mi / 1080 ft gain
    From your starting point at the Bear Mountain Inn, go left along the Cornell Mine Trail. (This part can be a bit confusing, but go past the carousel to a shaded picnic area; that is where the trail starts.) You will go under a bridge and follow the trail until it takes a sharp left and descends t...
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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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  • Highland Falls, New York

    Popolopen Torne

    4.5
    1.18 mi / 531 ft gain
    Popolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...
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  • New Paltz, New York

    Hike Mohonk Preserve's Gatehouse to Skytop Tower

    5.0
    9 mi / 1268 ft gain
    Begin at the intersection of Gatehouse Rd and Mohonk Private Rd. There is a small shoulder to park on here. Begin hiking into the preserve along the gatehouse road. There will be signs stating you need a membership or pass to enter. Don't worry about these, there will be a place on the trail ...
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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.0
    2 mi / 720 ft gain
    At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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  • New Windsor, New York

    Hike Jessup/West Ridge Loop via the Sweet Clover Trail

    10 mi / 1700 ft gain
    Schunnemunk Mountain State Park is one of my favorite parks.  It offers many trails and possibilities for different loops.  The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions.This hike starts at the Taylor Road parki...
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