Poughkeepsie, New York
Looking for the best hiking in Poughkeepsie? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Poughkeepsie. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Poughkeepsie
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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 -
Salisbury, Connecticut
Bear Mountain Loop
4.56.05 mi / 1516 ft gainAt 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...Read more -
Haines Falls, New York
Kaaterskill Falls
4.52.57 mi / 719 ft gainAlthough this is a super short hike, it is definitely a tough one! The quick, steep climb is totally worth it once you reach the 260 foot cascade and pool at the end. Hike along the trail, hugging Spruce Creek all the way to the falls. If you hike in the spring, the creek and the falls will be ra...Read more -
Elka Park, New York
Layman's Monument and Kaaterskill Falls
3.05 mi / 892 ft gainLayman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.Read more -
Greene County, United States
Hike to Newman's Ledge
4 mi / 584 ft gainLocated in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...Read more -
Haines Falls, New York
Summit North Mountain
4.56 mi / 855 ft gainHave you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills.Parki...Read more -
Pound Ridge, New York
Leatherman's Loop
1.25 mi / 1183 ft gainThis loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore. The Ward...Read more -
Mount Washington, Massachusetts
Explore Bash Bish Falls
4.21 miOne of my favorite walks to a spectacular falls. The trail is easy to follow and one mile from NY parking lot and 0.5 from the parking lot. The apparent place to swim. There are several very nice, family safe swimmable pools in the creek above and after the falls. There are signs at the top of t...Read more -
Mount Washington, Massachusetts
Guilder Pond and Mount Washington Lookout Trail
3.92 mi / 909 ft gainGuilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.Read more -
Sheffield, Massachusetts
Hike to Race Brook Falls
4.03.4 mi / 1174 ft gainHiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...Read more -
Big Indian, New York
Hike to Balsam Mountain in the Catskills
5.4 mi / 2910 ft gainTimeline: Weekend, though can easily be done as an overnight trip or just a day hike Summary: Day 1: Hike to camp (0.7 miles, 340' elevation gain) Day 2: Hike to Balsam Mountain and back to camp (4 miles round-trip) Day 3: Relax & hike back to car (0.7 miles) Details: Park the car at McKinle...Read more -
Tuxedo Park, New York
Hike to the Sterling Ridge Fire Tower
5.08.5 miStart out by turning right when you walk out of the visitor center onto Sterling Lake Loop (Blue Blazes). The visitor center is worth going in as they have a full diorama of the park with LED light to show trail routes. About .3 miles into the hike you will cross over a small bridge with a waterf...Read more -
Briarcliff Manor, New York
Hike Kate Kennard Trail
1.8 mi / 140 ft gainIf you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...Read more -
Hudson, New York
High Falls Conservation Area Loop
1.41 mi / 194 ft gainHigh Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.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 -
Norfolk, Connecticut
Hike to Campbell Falls
4.01.4 mi / 187 ft gainCampbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....Read more