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

  • Cold Spring, New York

    Mt. Taurus (Bull Hill)

    4.5
    3.52 mi / 1375 ft gain
    Mt. Taurus (or Bull Hill) is a short, family and dog friendly, hike just outside the town of Cold Spring, easily accessible by car or taking the train into town. It snakes along the edge of an old quarry that is just now being retaken by nature and provides lookouts towards the Hudson, other near...
    Read more
  • Cold Spring, New York

    Hike the Cornish/Brook/Notch/Washburn/Undercliff Loop

    8 mi / 1500 ft gain
    This loop is a great option to avoid crowds on the west side of the Washburn trail.  Start at the same trailhead for the Washburn Trail.  The Cornish Trail is on the left and there is an obvious sign at the trail split a few feet from the parking area.  The Cornish Trail is an old road from about...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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 ...
    Read more
  • Cold Spring, New York

    Sugarloaf Mountain and Breakneck Ridge Loop

    4.7
    4.33 mi / 1562 ft gain
    The Breakneck Ridge to Sugar Loaf Loop gives rise to various bypasses that offer hikers moderate to advanced terrain and multiple rock scrambles. The loop entails a total elevation gain of 1,670 feet and a total distance of 5.5 miles. The start of the trail begins at the (white blazes) at the no...
    Read more
  • Cold Spring, New York

    Breakneck Ridge Loop

    5.0
    5.91 mi / 1526 ft gain
    This short but steep loop hike in Hudson Highlands State Park offers multiple panoramic views of the Hudson River along the way. Please note that only experienced hikers should attempt this route – although the hike seems short, the elevation gain and steep rocky scrambles offer serious technical...
    Read more
  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...
    Read more
  • 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...
    Read more
  • Beacon, New York

    Sugarloaf Mountain via Wilkinson Memorial Trail

    5.0
    2.15 mi / 820 ft gain
    Trail is currently closed. Get updates at parks.ny.gov.  Sugarloaf Mountain is part of the Hudson Highlands State Park, along with Breakneck Ridge, Bull Hill, and Mt Beacon. Though the views are just as impressive as its sister trails, it is never as crowded and it's one of my favorite spots in ...
    Read more
  • 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 ...
    Read more
  • Tuxedo Park, New York

    Hike to the Sterling Ridge Fire Tower

    5.0
    8.5 mi
    Start out by turning right when you walk out of the visitor center onto Sterling Lake Loop (Blue Blazes). The visitor center is worth going in as they have a full diorama of the park with LED light to show trail routes. About .3 miles into the hike you will cross over a small bridge with a waterf...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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 ...
    Read more
  • 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...
    Read more