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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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
4.81.47 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 gainWalking the Brooklyn Bridge from the Brooklyn side is a rewarding experience that blends history, architecture, and stunning views of New York City. Start your journey at the pedestrian entrance near Cadman Plaza, which is easily accessible by subway (Court Street or High Street stations). The br...Read more -
Milford, Pennsylvania
Hike to Cliff Park Ridge
5.06.4 mi / 700 ft gainThis 6.4 mile out-and-back trail (2.7 miles each way) is an excellent trail for those looking to spend an early morning or afternoon outside without the strenuousness of all-out mountain hiking. Throughout the entire hike, there is only 700 ft. of elevation gain. Don't let this turn you away if y...Read more -
Milford, Pennsylvania
Raymondskill Falls
4.00.41 mi / 92 ft gainThis waterfall is just a short walk away from the main parking lot. Just a .30 mile hike will take you to a gorgeous three-tiered waterfall. There are platforms providing viewing areas to the falls. Raymondskill Falls is located in the northern portion of the Delaware National Water Gap Recreat...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 -
Brooklyn, New York
Brooklyn Botanical Gardens
5.01.34 mi / 75 ft gainBrooklyn Botanical Gardens is a loop trail that takes you by a lake located near New York City, New York.Read more -
Brooklyn, New York
Prospect Park Loop
4.73.65 mi / 223 ft gainThere are multiple places to enter Prospect Park. If you're looking for the main entrance to Prospect Park, it faces the stunning Soldiers' and Sailors' Arch in Grand Army Plaza. It is adjacent to the Brooklyn Botanical Garden, the flagship Brooklyn Public Library, and the Brooklyn Museum. As you...Read more -
Salisbury, Connecticut
Explore Riga Falls
The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...Read more -
Canaan, Connecticut
Explore Great Falls
3.00.5 miStumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.Read more