Highland, New York
Top Spots in and near Highland
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Cragsmoor, New York
Sam's Point, Ice Cave Trail, Verkeerderkill Falls
4.96.99 mi / 1063 ft gainLocated in Sam's Point Preserve, this hike has three major attractions – panoramic views from Sam's Point, mysterious and chilly Ice Caves, and a knee-weakening perch atop Verkeerderkill Falls. Pay attention to seasonal conditions before making this trip. Spring and early summer are best for see...Read more -
Cragsmoor, New York
Sam's Point Overlook to Ice Cave Trail
3.47 mi / 584 ft gainSam's Point Overlook to Ice Cave Trail is an out-and-back trail with scenic views near Lake Maratanza located near Ellenville, New York. This trail is dog friendly on-leash.Read more -
Kent, New York
King's Chamber and Moose Hill Loop
3.14 mi / 499 ft gainKing's Chamber and Moose Hill Loop is a loop trail that takes you by a lake located near Carmel, New York.Read more -
Cold Spring, New York
Photograph Indian Brook Falls
2.8This is about as short a walk and as little effort as you can put in for a beautiful waterfall. You can barely call it a hike, but I'll list it as such since you do walk through the woods for 5 minutes. The trail is extremely well built, and is pretty easily accessible through the winter.The trai...Read more -
Carmel Hamlet, New York
Ninham Mountain Fire Tower
5.01.23 mi / 367 ft gainThis is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...Read more -
New Windsor, New York
Hike Jessup/West Ridge Loop via the Sweet Clover Trail
10 mi / 1700 ft gainSchunnemunk Mountain State Park is one of my favorite parks. It offers many trails and possibilities for different loops. The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions.This hike starts at the Taylor Road parki...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 -
Philipstown, New York
Hike the Osborn Loop
7.6 mi / 850 ft gainThe Osborn Loop trail itself is not a loop. It connects to a 2.5 mile section of the Appalachian Trail. Hiking these together creates the loop. Start at the trail head for the Appalachian Trail on South Mountain Pass Road. There is parking for two or three cars. Walk up the road a short dist...Read more -
Grahamsville, New York
Swim at Peekamoose Blue Hole
3.8To get there: From Sundown, NY, head 10 miles on Route 42 until you see a large parking area on the right with a sign for the Peekamoose Mountain area. Follow the signs from the parking area to the creek. Swimming Hole Coordinates: (41.9182, -74.4215) You can cool off from NY's warm weather and d...Read more -
Philipstown, New York
Anthony's Nose via Appalachian Trail
4.61.95 mi / 682 ft gainParking for the trail runs along both sides of 9D right up until the Bear Mountain Bridge. It can be busy on the weekends so just make sure you're as far off the road as you can and be especially careful unloading kids and dogs. The trailhead is located at approximately 41.322571, -73.975949 and ...Read more -
Highland Falls, New York
Popolopen Torne
4.51.18 mi / 531 ft gainPopolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...Read more -
Monroe, New York
Hike the Jessup/Highlands/Long Path Trails
7.8 mi / 500 ft gainThis trails starts at a small park in Woodbury called Gonzaga Park. Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking. Three different trail names share this path. The Jessup trail starts/end at Gonzaga Park and trave...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 -
Bear Mountain, New York
Hike Bald Mountain, Bear Mountain State Park
4.76.8 mi / 1080 ft gainFrom your starting point at the Bear Mountain Inn, go left along the Cornell Mine Trail. (This part can be a bit confusing, but go past the carousel to a shaded picnic area; that is where the trail starts.) You will go under a bridge and follow the trail until it takes a sharp left and descends t...Read more -
Woodstock, New York
Sugarloaf Mountain via Blue Trail
6.54 mi / 2297 ft gainSugarloaf Mountain, is one the 35 highest peaks in New York's Catskills at 3806 ft. There are many ways to approach this peak, and this is an out-and-back hike via Mink Hollow. The parking area is located at the end of Milk Hollow Rd (42.10405386879072, -74.17148500019927). From here, get on the...Read more -
New Fairfield, Connecticut
Hike Squantz Pond Trail
2.2 mi / 321 ft gainThe hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...Read more