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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Jefferson, New Jersey
Thru Hike the Four Birds Trail
19 mi / 1200 ft gainThe 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...Read more -
Kent, Connecticut
Explore Kent Falls
5.00.75 mi / 250 ft gainEvery now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...Read more -
Washington, Connecticut
Hike Meeker Trail
3.3 mi / 639 ft gainMeeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.Read more -
Rye, New York
Hike the Marshlands Conservancy Loop
4.01.55 mi / 125 ft gainLocated 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 -
Rockaway, New Jersey
Hike the Timberbrook Pond - Riley's Rise Loop
5 mi / 500 ft gainThe trailhead parking is at the end of Timberbrook Road, before the road enters Camp Winnebago (Boy Scouts). I hiked this in a clockwise directions starting on the Timberbrook Trail (yellow markers). After about 1 mile the trail ends at a junction with the Four Birds Trail (white markers). Turn...Read more -
Stamford, Connecticut
Hike Cove Island Park Loop Trail
5.01.1 mi / 3 ft gainThis 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 -
Frankford, New Jersey
Picnic at the Sunrise Mountain Pavilion
This pavilion is one of the key features along the New Jersey section of the Appalachian Trail. There is a parking lot a very short hike part way down the mountain, but I recommend backpacking in from a different area to take in more of the beauty of the trail, mountains, and views in this area. ...Read more -
Englewood Cliffs, New Jersey
Hike the Dyckman Hill/Huyler's Landing Loop
9 mi / 980 ft gainThere 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 -
Sharon, Connecticut
Hike the Pine Knob Loop, Housatonic Meadows SP
5.02.5 mi / 770 ft gainThe Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick woods filled with vistas, wild flowers and tons of wild life. You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...Read more -
Boonton Township, New Jersey
Hike Pyramid Mountain to Tripod Rock
4.0This 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...Read more -
Washington, Connecticut
Hike the Mount Tom Tower Trail
1.3 mi / 337 ft gainStarting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...Read more -
Woodstock, New York
Overlook Mountain Trail
4.53 mi / 1348 ft gainIt is important to know that parking for the head of this trail is great, located on Meads Mountain Rd in Woodstock NY. The trail is clearly a gravel road marked by Red trail markers, on a gradual inline up to the Hotel first, at the 2 mile mark, and then the Fire Tower is 0.5 miles further down...Read more -
Englewood Cliffs, New Jersey
Hike the Dyckman Hill/Carpenter's Grove Loop
4.04 mi / 400 ft gainThis 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 -
Phoenicia, New York
Mt. Wittenberg
4.36.89 mi / 2608 ft gainLooking for a great day hike in the Catskill region of NY? Then you should definitely look into and consider tackling Mt. Wittenberg then. A challenging climb up but a very rewarding summit view. Starting at Woodland Valley Campgrounds visitor registration house (where you can pay for parking fo...Read more -
Phoenicia, New York
Camp at Woodland Valley
3.0If you are looking for a great campground up in the Catskill Mountains of New York then you definitely have to check out Woodland Valley Campgrounds. Located about 2 hours north of New York City, it is the perfect place to go to get off the grid. No service for about 30 minutes in any direction.T...Read more -
Big Indian, New York
Hike Giant Ledge
4.53.74 miThe trail starts across the street from the parking area you will see a sign. After a short walk in you will cross a foot bridge. At approximately 0.75 mile you will reach a junction. You will turn left toward Giant Ledge. The next half mile is fairly flat. At 1.5 miles you will reach a spur ...Read more