Chestertown, New York
Looking for the best hiking in Chestertown? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Chestertown. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Chestertown
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Lake Placid, New York
Great Range Traverse
20.15 mi / 6680 ft gainThe Summits: Mt. Marcy, Mt. Haystack, Little Haystack, Basin, Saddleback, Gothics, Armstrong, Upper Wolf Jaw, Lower Wolf Jaw, Hedgehog and Roostercomb. Total distance is around 25 Miles and an elevation change of over 17,600 feet (gain and loss). You will need to carry enough water for the day as...Read more -
Lake Placid, New York
Hike to Street and Nye Mountains
4.08.4 mi / 2500 ft gainStreet Mountain is number 31 at 4,166’ and Nye Mountain is number 45 at 3,895’ on the list of 46ers. The trails to both peaks are not maintained making these “trailless peaks”, but there is a pretty defined herd path and cairns, making it fairly easy to follow.Parking is at the Adirondack High P...Read more -
Lake Placid, New York
Hike Mount Jo
4.8This short hike offers exceptional views, perfect for late night sunsets and early morning sunrises. Take a lunch date to the summit and enjoy overlooking Heart Lake and New York's highest peak, Mt. Marcy. The trail to Mt. Jo trailhead is located at the enterance station near the parking lot at t...Read more -
Long Lake, New York
Hike to Owls Head Mountain Fire Tower in Sargent Ponds Wild Forest
5.06.2 mi / 1500 ft gainOwls Head Mountain is an Adirondack Fire Tower Mountain with an elevation of 2,812 feet. It is located in Long Lake in the Sargent Ponds Wild Forest and is a 6.2 mile out and back round trip hike. The trail head is located on Endion Ln, 2 miles north of the hamlet of Long Lake heading towards Tup...Read more -
North Elba, New York
Hike Cascade & Porter Mountains
4.74.8 mi / 1900 ft gainCascade 4,098ft and Porter 4,084ft are two easy peaks which are usually hiked together. The trail starts on Rt 73 and you starts climbing up slowly but not challenging at all. Is 2.4 mIles to summit of cascade, the last 0.2 miles is a open rock scrambling but I'm the winter when the weather is b...Read more -
Dorset, Vermont
Hike 'The Merck'
4.02.5 miOf the 10 trails at The Merck, The Wildlife Trail is a great hike through the forest that offers you the best way to see wildlife, streams and tracks. You can do the whole hike as a loop in about 2-2 1/2 hours or shorten it up with some shortcuts if you just want a quick hike. Great for family ...Read more -
Salisbury, Vermont
Camp at Lake Dunmore
The campground office for Branbury state park is on the opposite side of Route 53 from the pin on the map here, but the best campsites are where the pin is. Start by going and talking to the rangers at the office, they are super friendly and very helpful for recommendations of hikes or things to...Read more -
Inlet, New York
Hike to Shallow Lake in the Pigeon Lake Wilderness
2.8 miShallow Lake is a 268 acre remote lake located in the Pigeon Lake Wilderness in Central Adirondacks. This trail starts from Brown Tract Pond Campground, near campsite number 68 via the Shallow Lake Trail. This is a nice and easy hike for all fitness levels, with little elevation gain.There is a w...Read more -
Wallingford, Vermont
Hike the White Rocks Ice Beds Trail
1.6 mi / 180 ft gainThis 1.6 mile round trip hike starts from the Ice Beds parking lot in the Green Mountain National Forest in Vermont. The trailhead is close to the parking lot entrance, following the blue-blazed trail. Be sure to read the signs, as the far trailhead is a hike to the cliffs, not the ice beds. Af...Read more -
Mendon, Vermont
Hike to Killington Peak
5.03.4 miThe trail head (Bucklin Trail) is found a couple of miles up Wheelerville Road on the left. Wheerlerville is a dirt road that will be muddy in the spring and summer. The drive is long enough that you will think you did something wrong, but you haven't! the trail head will eventually pop up.The tr...Read more -
Lake Placid, New York
Hike Up Cobble Hill
5.0Looking for a great family hike up in the Adirondacks? Take a look into Cobble Hill right off of Mirror Lake in Lake Placid. This is a perfect hike for those with younger kids and want to expose them to hiking.Cobble Hill has a little bit of everything all packed into the short distance. The tr...Read more -
Caroga Lake, New York
Kane Mountain Fire Tower
4.22.1 mi / 518 ft gainThe Kane Mountain fire tower is one of the more frequented Adirondack towers due to the ease of the trail and its proximity to so many Caroga Lake camping areas. The short hike is family friendly and available year round, part of the trail doubles as a cross country skiing trail in fact. Driving...Read more -
Lake Placid, New York
Hike to McKenzie and Haystack Mountains
12.4 mi / 4100 ft gainMcKenzie Mountain stands at 3,861 feet and is one of the highest 100 in the Adirondacks. Haystack Mountain stands at 2,874 feet. Both are part of the Saranac 6ers Challenge.The trailhead for this route to McKenzie and Haystack is located on route 86 in Ray Brook, there is a nice parking area off ...Read more -
Lake Clear, New York
Hike to the Summit of Ampersand Mountain
4.55.2 mi / 1775 ft gainAmpersand Mountain is part of the Saranac Lake 6er Hiking Challenge. It is one of six mountains surrounding Saranac Lake. The trail starts just across the street from the parking area. Though there is ample parking it can full up on a good day as it is a popular hike. The trail begins over most...Read more -
Lake Clear, New York
Relax at Ampersand Beach
1.1 mi / 20 ft gainLocated across from the Ampersand Mountain trailhead on NY Route 3, a trail will take you a short walk (about a half mile) to this beautiful, quiet beach on the shores of Middle Saranac Lake. Starting at the trailhead, you will continue along an unmarked but clear footpath that trails through the...Read more -
Inlet, New York
Hike Black Bear Mountain
5.03.8 mi / 2442 ft gainThe trail up Black Bear starts at the end of the old road/parking lot nearest Inlet. There are two routes up Black Bear; the shorter but steeper route of 1.9 miles and the longer but muddier route of 3.1 miles. There is another trailhead on Uncas Road that isn't as steep but is 2.2 miles to the s...Read more