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Pine Plains, New York

Top Spots in and near Pine Plains

  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    7.5 mi / 1174 ft gain
    There are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road.  I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things.  For the most part the hike is flat but at some parts it c...
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  • New Windsor, New York

    Hike Jessup/West Ridge Loop via the Sweet Clover Trail

    10 mi / 1700 ft gain
    Schunnemunk 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...
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  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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  • Voorheesville, New York

    Hike the Keleher Preserve Loop

    2.0
    3 mi / 1636 ft gain
    The historic preserve is operated by the Mohawk Hudson Land Conservancy, so trails are clearly marked and extremely well maintained. There are features of the original farm that the land was used for from the 18th Century, including hand-thrown stone walls and an old logging road that cuts throug...
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  • Philipstown, New York

    Hike the Osborn Loop

    7.6 mi / 850 ft gain
    The 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...
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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  • Philipstown, New York

    Anthony's Nose via Appalachian Trail

    4.6
    1.95 mi / 682 ft gain
    Parking 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 ...
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  • Highland Falls, New York

    Popolopen Torne

    4.5
    1.18 mi / 531 ft gain
    Popolopen 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...
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  • Bear Mountain, New York

    Hike Bald Mountain, Bear Mountain State Park

    4.7
    6.8 mi / 1080 ft gain
    From 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...
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  • Cortlandt, New York

    Hike the Camp Smith Trail

    4.5
    5.92 mi / 1759 ft gain
    This approximately 3-hour hike borders the Hudson River, and is one of the best in Westchester County. Start off at the parking area at the Bear Mountain Tollhouse, or at a small parking area farther up Bear Mountain Road, if you want a slightly shorter hike. The trail is fairly steep in places, ...
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  • Voorheesville, New York

    Hike the Indian Ladder Trail

    4.5
    3.5 mi / 200 ft gain
    There are many parking areas within the park. Park at the overlook parking. From here you head west following the wood fence. This is the Cliff Top trail. Approximately after walking 0.5 miles you will reach the stairs that will lead you to the base of the cliffs. This marks the start of the...
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  • Southington, Connecticut

    Rock Climb Ragged Mountain

    The main face of Ragged Mountain (elev. 761 feet) is home to a lot climbing in central Connecticut. It runs north-south for about 600 feet. Its max height of 100 feet. The crag is home to several rock climbing guides and schools. Routes range in difficultly from great for the beginner (5.3) to su...
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