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Poughkeepsie, New York

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

Top Chillin Spots in and near Poughkeepsie

  • Sheffield, Massachusetts

    Hike to Race Brook Falls

    4.0
    3.4 mi / 1174 ft gain
    Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
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  • Warwick, New York

    Enjoy a Film at the Historic Warwick Drive-In

    Take a trip back in time at the Warwick Drive-In and watch a feature film on the big screen. The Drive-In shows movies just in theaters and older films with three different screens / options to chose from. The theater sells tickets for both one movie and for double features, i.e. watch two movies...
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  • Ringwood, New Jersey

    Explore Ringwood Manor State Park

    5.0
    1.3 mi
    On my way to the drive-in, I saw a sign for Ringwood Manor estate and wanted to adventure around. The parking is easy and the property was beautiful!As we walked through the estate, we found:a quaint tree foresta small cemetery with headstones hundreds of years olda river with a small waterfall ...
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  • Norfolk, Connecticut

    Hike to Campbell Falls

    4.0
    1.4 mi / 187 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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  • West Milford, New Jersey

    Hike the Terrace Pond North - South Loop

    10.7 mi / 1200 ft gain
    From Warwick Road, parking at the northernmost road side parking area, cross the road, and the Terrace Pond North trail (marked with blue blazes) begins as a steady climb until you gain a ridge that offers some great views for several miles. Eventually, you'll reach a power line where you turn ri...
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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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  • 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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