Sherman, Connecticut
Looking for the best hiking in Sherman? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Sherman. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Sherman
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Yonkers, New York
Run the Old Croton Aqueduct Trail
5.026.5 miThis trail traces the route of the Old Croton Aqueduct, which carried water to New York City between 1842 and 1955. Our recommended route starts near the Greystone Station in Yonkers, NY (Metro-North Hudson Line) and ends by the Scarborough Station, but you can easily modify your route – the enti...Read more -
Great Barrington, Massachusetts
Hike Monument Mountain
4.52 mi / 720 ft gainAt 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...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 -
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 -
Tuxedo Park, New York
Sterling Lake & Fire Tower Loop
5.07.54 mi / 1239.06 ft gainStart 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 -
Glastonbury, Connecticut
Hike the Cotton Hollow Nature Preserve
5.03 miThere are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...Read more -
Woodcliff Lake, New Jersey
Wood Dale Park Loop
4.00.38 mi / 16 ft gainLocated within the Wood Dale County Park in Woodcliff Lake, New Jersey, the Wood Dale Park Loop offers visitors a tranquil walking experience amidst lush greenery and a picturesque pond. This family-friendly loop is ideal for leisurely strolls, jogging, and nature observation. Trail Overview ...Read more -
Middlesex County, Connecticut
Hike to Glen Falls
5.00.75 miAccessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...Read more -
Closter, New Jersey
Hike to Huyler's Landing/ Closter Dock Loop
4.05.4 mi / 450 ft gainThe easiest way to access this loop hike is by parking at the Palisades State Park Headquarters. This is just off exit 2 from the Palisades Interstate Parkway. Parking here is free and it is a short walk down a road to the Closter Dock Trail. The Closter Dock Trail is more of a wide fire road ...Read more -
Elka Park, New York
Hike to Plattekill Falls
0.5 mi / 137 ft gainJust outside of Elka Park, New York, Plattekill Falls is accessible from Albany and New York City alike. This is a great hike for families and all skill levels. The falls are spectacular year-round, but the best time to visit is in the spring. From the trailhead, walk left past the red house unt...Read more -
Elka Park, New York
Hike to Huckleberry Point
4.54.5 mi / 644 ft gainThis is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...Read more -
Elka Park, New York
Kaaterskill High Peak Trail
7.85 mi / 1982 ft gainThere are no direct views from the summit, so it is recommended to take the .25 mile shoot-off trail to Hurricane Ledge for beautiful views of the surrounding mountains and valleys. In the spring, wildflowers line the trail. If you look carefully in the brush, you'll find wreckage from two old pl...Read more -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...Read more -
Elka Park, New York
Hike Indian Head Summit via Jimmy Dolan Notch Overlook
4.9 mi / 1512 ft gainThe view from the summit of this hike is incredible. Bring a sack lunch and a camera - you'll want to stay for a while! This trail is open for use year-round and provides great snowshoeing in the winter and fabulous wildflowers in the spring and summer. This is also a great location for birding!Read more -
Elka Park, New York
Devil's Path to Devil's Tombstone
5.011.9 mi / 4475 ft gainThe Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...Read more -
Elka Park, New York
Devil's Path in the Catskills
4.022.04 mi / 7733 ft gainDevil's Path is roughly more than 24 miles long, althought it feels like an eternity of milage. Going thru the summits of Indian head, Twin, Sugarloaf, Plateau, Hunter, and Westkill Mountains. Its brutal. Its painful, Its unique. Be prepared for anything and everything. You will encounter wild l...Read more