New Windsor, New York
Looking for the best hiking in New Windsor? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around New Windsor. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near New Windsor
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West Milford, New Jersey
Hike the Terrace Pond North - South Loop
10.7 mi / 1200 ft gainFrom 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...Read more -
New Fairfield, Connecticut
Hike Squantz Pond Trail
2.2 mi / 321 ft gainThe 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 -
608 Ramapo Valley Road, New Jersey
Hike the Halifax Trail and Ruins in the Ramapo Valley Reservation
8.25 mi / 500 ft gainTo start, I recommend coming in the early morning or afternoon, as the parking lot fills up with people hiking, fishing or going for a walk with their family. I usually get my luckiest before 9. This park is as relaxing or exciting as you want to make it. Here is a good map to use/ print out. We ...Read more -
Vernon Township, New Jersey
Stairway to Heaven
4.86.8 mi / 1089 ft gainThis popular hike starts out on the Appalachian Trail (AT, white blazes). You begin on a boardwalk that crosses over a marsh, then you leave the boardwalk and enter a forested area. At around 1.4 miles, follow a bicycle path, Canal Road, then turn right, cross over a bridge, and take a left throu...Read more -
Dover Plains, New York
Hike Dover's Stone Church
4.5Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...Read more -
Danbury, Connecticut
Hike Middle Mountain To Thomas Mountain Loop
3.7 mi / 856 ft gainMiddle 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 -
Allendale, New Jersey
Celery Farm Mayor Fitzpatrick Nature Trail
3.01.2 mi / 92 ft gainThe Celery Farm Mayor Fitzpatrick Nature Trail in Allendale, New Jersey, is a peaceful, scenic retreat for birdwatchers, hikers, and nature lovers. This 1-mile loop trail winds through a 107-acre freshwater wetland preserve, offering opportunities to spot over 240 bird species, deer, turtles, a...Read more -
Woodcliff Lake, New Jersey
Wood Dale Park Loop
4.00.38 mi / 16 ft gainLocated within the Wood Dale County Park in Woodcliff Lake, New Jersey, the Wood Dale Park Loop offers visitors a tranquil walking experience amidst lush greenery and a picturesque pond. This family-friendly loop is ideal for leisurely strolls, jogging, and nature observation. Trail Overview ...Read more -
Kent, Connecticut
Hike the Ridge Loop Trail, Macedonia Brook SP
3.0For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...Read more -
Closter, New Jersey
Alpine White Trail (Stateline Lookout)
5.03.86 mi / 856 ft gainStarting 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 -
Ridgewood, New Jersey
Saddle River Trail
5.0Saddle River Trail is an out-and-back trail that takes you by a lake located near Fair Lawn, New Jersey.Read more -
Sussex, New Jersey
Camp at High Point State Park
4.0You'll need at least a weekend to sample all that High Point State Park has to offer. One of the park's must-do hikes is to High Point Monument (1,803 ft), where you have panoramic views of the Pocono and Catskill Mountains, and the Wallkill River Valley. Additionally, there are 50 total miles of...Read more -
89 Van Orden Road, New Jersey
Hike the Hank's Pond Loop
7 mi / 500 ft gainHank's Pond loop can be accessed from the south at the corner of Clinton road and Van Orden road or from the north, parking at the lot on Stephens road. I hiked from the south on this trip. Follow the wide trail known as Hank's East trail marked with white blazes. Soon you will reach a trail c...Read more -
Wantage, New Jersey
Hike the Iris Tail - Appalachian Tail Loop
4.09 mi / 1000 ft gainStart this hike from the Appalachian Trail parking area off route 23, south bound side, south of the park office. Follow the Blue Dot trail until is intersects with the Iris Trail. The Iris Trail (marked with red blazes) is a through hike that is about 5 miles long. It parallels the Appalachian T...Read more -
Yonkers, New York
Run the Old Croton Aqueduct Trail
5.026.5 miThis 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 to Huyler's Landing/ Closter Dock Loop
4.05.4 mi / 450 ft gainThe 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