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Greenwich, Connecticut

Top Spots in and near Greenwich

  • 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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  • Monroe, New York

    Hike the Jessup/Highlands/Long Path Trails

    7.8 mi / 500 ft gain
    This trails starts at a small park in Woodbury called Gonzaga Park.  Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking.  Three different trail names share this path.  The Jessup trail starts/end at Gonzaga Park and trave...
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  • Beacon, New York

    Mt. Beacon Fire Tower

    4.8
    3.83 mi / 1332 ft gain
    Mount Beacon is a very popular trail along the Hudson River, and for good reason. It offers a good workout, fantastic views for both sunrise and sunset (and of course the time in between), a recently rebuilt fire tower, and all with incredibly easy access right on the edge of a lively town. The ...
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  • Beacon, New York

    Malouf's Mountain Camp on Mt. Beacon

    7.02 mi / 2087 ft gain
    Starting in the quaint town of Beacon there are a couple of options for hikes of varying difficulty. From the station the walk is about 1.5 miles to the trail heads, alternatively if you choose to stay the night at Malouf's Mountain Sunset Campground you can arrange for the host to meet you, take...
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  • Beacon, New York

    Hike the Scofield Ridge Loop

    7.5 mi / 1850 ft gain
    There are some great view points along this route.  Start from the Mount Beacon Park trailhead parking area.  This leads to the Casino Trail (red markers).  The trail climbs steeply to some old ruins of a casino.  Most of what remains is only the brick structure housing the mechanics for a trolle...
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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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  • 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

    Explore Long Dock and Dennings Point Parks

    4.0
    Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...
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  • West Milford, New Jersey

    Hike Bearfort Mountain

    5.0
    5.06 mi / 1007 ft gain
    Bearfort Mountain is a great weekend morning hike that borders NJ and NY. Parking can be tricky as the entrance to the lot looks like it is Greenwood Lake Marina's boat storage area. Once parked, find the trail entrance at the top of the little hill and continue to the blue on white marked trail....
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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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  • Boonton Township, New Jersey

    Hike Pyramid Mountain to Tripod Rock

    4.0
    This is a fun hike that is great for the entire family. The trails are really well maintained and Tripod Rock is a pretty amazing feature to check out. You can hike to the rock and follow your steps back to the parking lot for a 3 mile round trip or continue along the trail for a 4.4 mile loop. I...
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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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  • Hamden, Connecticut

    Mountain Bike West Rock Ridge State Park

    West Rock Ridge State Park is a 700 ft high scenic ridge that is located on the west side of New Haven. There are tons of good mountain biking trails located all around the ridge that can satisfy all types of skill levels. The easiest place to park is the Lake Wintergreen parking lot, which sits ...
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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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  • Staten Island, New York

    Hike the Staten Island Greenbelt

    4.0
    7.6 mi
    The white trail offers one of the two more ambitious hikes, passing through Egbertville Ravine, Heyerdahl Hill and Buck’s Hollow parks on Staten Island, offering an up-close view of the forest and marshland that once covered the island. About midway, the trail also passes the Greenbelt Nature Cen...
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  • Jefferson, New Jersey

    Thru Hike the Four Birds Trail

    19 mi / 1200 ft gain
    The Four Birds Trail is about 19 miles long and is a great thru hike or can be done in sections as out and back hikes or part of loop hikes with other trails.  Starting from the north, the trail ascends gradually over easy terrain until you reach a cliff ridge.  There are several good view points...
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