Philipstown, New York
Looking for the best hiking in Philipstown? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Philipstown. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Philipstown
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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 -
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 -
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 -
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 -
Cedar Grove, New Jersey
Hike at Mills Reservation
4.72 mi / 200 ft gainMills Reservation is over 150 acres of wooded area located off of Normal Ave. near the Cedar Grove reservoir. Parking space is limited due to the small size but there is another hidden lot towards the back if you make a right out of the parking lot and then the first right turn onto Highland Ave....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 -
Bridgeport, Connecticut
Stroll around Fayerweather Island
0.5 miParking 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 -
New York, New York
Jacqueline Kennedy Onassis Reservoir Running Path
5.01.68 mi / 69 ft gainJacqueline 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 gainNorthwest Central Park Loop is a loop trail that takes you by a lake located near New York City, New York.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 -
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 -
New York, New York
High Line
4.61.47 mi / 26 ft gainBuilt on a historic freight rail line and perched above the streets of Manhattan’s West Side, the High Line is a public park that features a green-lined walkway. Park hours depend on the season, although it never opens before 7am, so best to go for sunset. Although you may have some company on wa...Read more -
Sandyston, New Jersey
Explore the Sussex County Sunflower Maze
5.03 miI stumbled upon the Sunflower Maze by accident when I was driving through NJ and was quickly distracted by the enormous yellow flowers. So of course, I had to check it out! It opens at 9AM and last admission is at 6PM. The maze is only open from around August to October for the flower bloom. 3...Read more -
Sandyston, New Jersey
Hike the AT to Culvers Lookout Tower
3.2 miStart your journey in Stokes State Forest at the Culver Gap Parking Lot, located at 41.180239, -74.787954. From the parking lot, jump on over to the Appalachian Trail and hike Northbound. You know you're headed the right way if you are going away from the small town and cross over Sunrise Mountai...Read more -
New York, New York
Brooklyn Bridge Walk
5.02.4 mi / 26 ft gainBrooklyn Bridge Walk is an out-and-back trail that takes you by a river located near New York City, New York.Read more -
Brooklyn, New York
Brooklyn Bridge Walk via Brooklyn
4.71.12 mi / 0 ft gainBrooklyn Bridge Walk via Brooklyn is a point-to-point trail that takes you past scenic surroundings located near New York City, New York.Read more