Outbound Collective logo

Greenwich, Connecticut

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

Top Hiking Spots in and near Greenwich

  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • Yonkers, New York

    Run the Old Croton Aqueduct Trail

    5.0
    26.5 mi
    This trail traces the route of the Old Croton Aqueduct, which carried water to New York City between 1842 and 1955. Our recommended route starts near the Greystone Station in Yonkers, NY (Metro-North Hudson Line) and ends by the Scarborough Station, but you can easily modify your route – the enti...
    Read more
  • 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...
    Read more
  • Pound Ridge, New York

    Leatherman's Loop

    1.25 mi / 1183 ft gain
    This loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore. The Ward...
    Read more
  • 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 ...
    Read more
  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Huyler's Landing Loop

    9 mi / 980 ft gain
    There is two ways to access this loop hike.  The first is from the Englewood Picnic area just off Exit 1 from the Palisades Interstate Parkway.  Parking here requires a fee of $5 May through September. The second is to drive past the Englewood Picnic area turnoff on Henry Hudson Drive and continu...
    Read more
  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Carpenter's Grove Loop

    4.0
    4 mi / 400 ft gain
    This loop hike can be started from several different places.  I chose to start from Allison Park which overlooks the Hudson River in Englewood Cliffs, NJ.  From the parking area, walk out to the entrance road and travel south to Saint Peter's College.  The Long Path Trail, which you join from All...
    Read more
  • 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...
    Read more
  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    7.5 mi / 1174 ft gain
    There are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road.  I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things.  For the most part the hike is flat but at some parts it c...
    Read more
  • New York, New York

    Jacqueline Kennedy Onassis Reservoir Running Path

    5.0
    1.68 mi / 69 ft gain
    Jacqueline Kennedy Onassis Reservoir Running Path is a loop trail that takes you by a lake located near New York City, New York.
    Read more
  • New York, New York

    Northwest Central Park Loop

    3.63 mi / 164 ft gain
    Northwest Central Park Loop is a loop trail that takes you by a lake located near New York City, New York.
    Read more
  • 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, ...
    Read more
  • Danbury, Connecticut

    Hike Middle Mountain To Thomas Mountain Loop

    3.7 mi / 856 ft gain
    Middle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.
    Read more
  • 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...
    Read more