Pittsfield, Massachusetts
Top Spots in and near Pittsfield
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Voorheesville, New York
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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Shaftsbury, Vermont
4.0
1.39 mi
/ 160.98 ft gain
Lake Shaftsbury State Park is a small park in Southern Vermont between Bennington and Manchester. It is well-loved by locals as swimming spot in the summer, especially for families with kids. Less well known is the nature trail that meanders around the perimeter of the lake. While only a mile in...
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New Scotland, New York
4.5
1.62 mi
/ 230 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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Erving, Massachusetts
Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.
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Sharon, Connecticut
The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick woods filled with vistas, wild flowers and tons of wild life. You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide.
Pine Knob is a blue blaze ...
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Stanfordville, New York
The Wethersfield Estate is a beautiful estate and property located less than 2 hours north of New York City. The gardens are expansive and extremely beautiful, open to the public each day from noon to 5pm (COVID-19 hours). Additionally, there are trails for horseback rides, carriage rides, dog-wa...
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Greene County, United States
Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
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Tannersville, New York
4.7
6.16 mi
/ 1060 ft gain
Have you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills.
Par...
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Palenville, New York
4.5
1.67 mi
/ 360.89 ft gain
This short hike is one of the most popular in the Catskills — and for good reason. From the Laurel House Road Trailhead, it’s less than a mile round trip to reach Kaaterskill Falls, New York’s tallest two-tiered waterfall, with a dramatic 260-foot drop into a rocky amphitheater.
The trail itse...
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Haines Falls, New York
Please be respectful if visiting this local swimming hole. Pack out what you pack in, carry out others' trash, and familiarize yourself with Leave No Trace principles.
Hidden in the Catskill Mountains is one of the coolest cliff jumping locations I have ever been to. The first time I went was a...
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Elka Park, New York
Layman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.
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Tannersville, New York
5.0
3.61 mi
/ 246 ft gain
The Kaaterskill Rail Trail begins near Haines Falls, New York heading toward North and South Lake. The trail is set in a gorgeous forest, and is used for hiking, trail running, and birding trips. The trail provides exceptional views of the surrounding mountains, valleys, forests, and towns.
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Altamont, New York
3.0
1.93 mi
/ 256 ft gain
Over 3 miles of trails provide access to all parts of the preserve, and end up winding through mixed terrain including a wetland, waterfalls, and old stone walls. The property crosses the Bozenkill Road at two points on either side of private parcels (with beautiful homes), so be vigilant there; ...
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Kent, Connecticut
5.0
0.75 mi
/ 250 ft gain
Every 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...
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Elka Park, New York
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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Elka Park, New York
There are no direct views from the summit, so it is recommended to take the .25 mile shoot-off trail to Hurricane Ledge for beautiful views of the surrounding mountains and valleys. In the spring, wildflowers line the trail. If you look carefully in the brush, you'll find wreckage from two old pl...
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