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Hillsdale, New York

Looking for the best hiking in Hillsdale? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Hillsdale. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Hillsdale

  • Woodstock, New York

    Sugarloaf Mountain via Blue Trail

    6.54 mi / 2297 ft gain
    Sugarloaf 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...
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  • Williamstown, Massachusetts

    Hike Mt. Greylock via Money Brook Trail

    9.7 mi / 3034 ft gain
    Park in the parking lot on Hopper Rd. Walk to the end of the road where you will find the Hopper Trailhead. Take the right fork. The Money Brook trail will take you to a waterfall, the Mt. Greylock summit, and back to the end of Hopper Rd. The trail is long but worth the hike, exploring parts of ...
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  • Windham, New York

    Backpack the Catskill's Escarpment Trail

    32.4 mi / 8000 ft gain
    The Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...
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  • Savoy, Massachusetts

    Tannery Falls Loop

    0.54 mi / 135 ft gain
    The hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...
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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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  • Albany, New York

    Blueberry Hill East

    1.73 mi / 59 ft gain
    Blueberry Hill East is a loop trail where you may see beautiful wildflowers located near Albany, New York.
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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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  • Albany, New York

    Blueberry Hill West Red and Yellow Trail

    1.37 mi / 52 ft gain
    Blueberry Hill West Red and Yellow Trail is a loop trail where you may see beautiful wildflowers located near Albany, New York.
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  • High Falls, New York

    Scramble Bonticou Crag and Table Rocks

    4.5
    This is not a hike for the inexperienced. There is a very steep rock scramble that has some dangerous section if you are not aware of your footing and positioning. For those up to the challenge, it is extremely rewarding at the top.To start, each person has to pay $12 to access the Monhonk Preser...
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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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  • Cropseyville, New York

    Hike Dickinson Hill Fire Tower

    4.5
    3 mi / 200 ft gain
    Once you drive onto N. Long Pond Road you will follow it appproximately 1.5 miles to the end. From the parking you can take the short walk back on the road to the start of the trail. The trail is actually a rough Fire Tower Road. You will follow this for about 1.3 miles. Here you will see a se...
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  • High Falls, New York

    Mohonk Mountain House Labyrinth and Lemon Squeeze Hike

    4.5
    Mohonk Mountain House is a historic resort located just outside the Catskills in the Hudson Valley just 90 miles north of New York City. With 85 miles of winding trails throughout the Mohonk Preserve, you'll have endless hiking options upon your arrival.Parking at the Gatehouse is limited, so be ...
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  • Holyoke, Massachusetts

    Whiting Street Reservoir Loop

    3.74 mi / 138 ft gain
    Whiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.
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  • New Paltz, New York

    Hike Mohonk Preserve's Gatehouse to Skytop Tower

    5.0
    9 mi / 1268 ft gain
    Begin at the intersection of Gatehouse Rd and Mohonk Private Rd. There is a small shoulder to park on here. Begin hiking into the preserve along the gatehouse road. There will be signs stating you need a membership or pass to enter. Don't worry about these, there will be a place on the trail ...
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  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The 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...
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  • Phoenicia, New York

    Hike Mt. Wittenberg

    4.3
    Looking for a great day hike in the Catskill region of NY? Then you should definitely look into and consider tackling Mt. Wittenberg then. A challenging climb up but a very rewarding summit view.Starting at Woodland Valley Campgrounds visitor registration house (where you can pay for parking for ...
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