• United States
  • Connecticut
  • Litchfield County
  • Litchfield County, Connecticut

    Top Spots in and near Litchfield County

    • Cold Spring, New York

      Hike the Cornish/Brook/Notch/Washburn/Undercliff Loop

      8 mi / 1500 ft gain
      This loop is a great option to avoid crowds on the west side of the Washburn trail.  Start at the same trailhead for the Washburn Trail.  The Cornish Trail is on the left and there is an obvious sign at the trail split a few feet from the parking area.  The Cornish Trail is an old road from about...
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    • Cold Spring, New York

      Mt. Taurus (Bull Hill)

      4.5
      3.52 mi / 1375 ft gain
      Mt. Taurus (or Bull Hill) is a short, family and dog friendly, hike just outside the town of Cold Spring, easily accessible by car or taking the train into town. It snakes along the edge of an old quarry that is just now being retaken by nature and provides lookouts towards the Hudson, other near...
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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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    • Bridgeport, Connecticut

      Stroll around Fayerweather Island

      0.5 mi
      Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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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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    • Cornwall, New York

      Storm King Mountain Loop

      4.6
      2.44 mi / 400 ft gain
      This is an easy, yet very rewarding hike with a lot of viewpoints on the way up. Technically you scale up two mountains, Butter Hill and Storm King, but most people just describe it as Storm King Mountain. This is a great hike for families with younger kids, those who don't have much time but wan...
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    • Cornwall, New York

      Hike the North Point Loop

      6.5 mi / 1400 ft gain
      There is three different trailheads to access the North Point Loop.  I chose the trailhead that would give me the longest hike.  That would be the Butter Hill parking area on Route 9W north.  From the parking lot, start on the connector trail designated with white markers.  Follow this for about ...
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    • Cornwall-on-Hudson, New York

      Hike the Stillman - Bluebird Loop

      5.4 mi / 1200 ft gain
      This loop hike starts at the northern trailhead of the park where the Stillman Trail begins.  The parking area has enough space for only 6 or 7 cars.  Start off on a wide maintained carriage road.  After about a half mile, the Stillman Trail (yellow markers) breaks of to the left.  However, stay ...
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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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    • 3197 U.S. 44, New York

      Hike to Sky Top via the Undercliff Road

      7.3 mi / 900 ft gain
      Starting from the East Trapps parking area ascend the East Trapps connector trail marked with yellow blazes.  You can also park at the Mohonk Preserve visitor center where you can purchase your access pass ($15 per person) and pick up a free map of the presere trails and carriage roads.  The conn...
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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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    • Gardiner, New York

      Hike The Millbrook Mountain Ridge Trail

      5.0
      7 mi / 1400 ft gain
      Want to walk on the edge? visit Millbrook Mountain in the Catskills of NY. This loops hike follows the mountains ridge line most of the way to the summit with multiple viewpoints and cliff ledges to walk out on. This hike is recommended those in the area.Park at West Trapps Parking Lot and head ...
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    • Gardiner, New York

      Hike the Dickie Barre, Peters Kill and Awosting Falls Loop

      3.0
      7.8 mi
      This loop hike takes you to Awosting Falls (65 ft.), as well as to great  valley views along the ridge of Dickie Barre, and across Peters Kill, on the way.Start out on West Trapps Connector Trail (yellow blazes) at the east end of the West Trapps parking lot (get their early because the lot will ...
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    • Gardiner, New York

      Hike the Overcliff - Undercliff Road Loop

      5.3 mi / 350 ft gain
      From the West Trapps parking lot ($15 for hikers), walk to the end of the parking lot and past a large kiosk.  The trail connects the parking lot to the Overcliff Road/Undercliff Road junction.  The loop can be done in either direction.  I turned left on the Overcliff Road.  This takes you behind...
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    • Woodstock, New York

      Overlook Mountain Trail

      4.53 mi / 1348 ft gain
      It 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...
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    • Elka Park, New York

      Hike to Huckleberry Point

      4.5
      4.5 mi / 644 ft gain
      This 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...
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