Pound Ridge, New York
Looking for the best hiking in Pound Ridge? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Pound Ridge. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Pound Ridge
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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 -
Hamden, Connecticut
Hike the Tower Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...Read more -
Hamden, Connecticut
Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSince I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...Read more -
Hamden, Connecticut
Boulder & Free Climb off the Blue Trail In Sleeping Giant SP
Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...Read more -
Cheshire, Connecticut
Hike to Roaring Brook Falls
1.2 mi / 377 ft gainArriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...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 -
West Milford, New Jersey
Hike Bearfort Mountain
5.05.06 mi / 1007 ft gainBearfort Mountain is a great weekend morning hike that borders NJ and NY. Parking can be tricky as the entrance to the lot looks like it is Greenwood Lake Marina's boat storage area. Once parked, find the trail entrance at the top of the little hill and continue to the blue on white marked trail....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 -
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 -
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 -
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 -
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 -
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 -
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
4.03.65 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 -
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