Pittsfield, Massachusetts

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

Top Hiking Spots in and near Pittsfield

  • New Scotland, New York

    Indian Ladder Trail

    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

    1.97 mi / 676 ft gain
    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

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    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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  • Greene County, United States

    Hike to Newman's Ledge

    4 mi / 584 ft gain
    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

    North Mountain

    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

    Kaaterskill Falls via Laurel House

    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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  • Elka Park, New York

    Layman's Monument and Kaaterskill Falls

    3.05 mi / 892 ft gain
    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

    Kaaterskill Rail Trail + Kaaterskill Falls

    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

    Wolf Creek Falls Preserve White Trail Loop

    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

    Explore Kent Falls

    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

    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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  • Elka Park, New York

    Kaaterskill High Peak Trail

    7.85 mi / 1982 ft gain
    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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  • Elka Park, New York

    Hike to Plattekill Falls

    0.5 mi / 137 ft gain
    Just outside of Elka Park, New York, Plattekill Falls is accessible from Albany and New York City alike. This is a great hike for families and all skill levels. The falls are spectacular year-round, but the best time to visit is in the spring.  From the trailhead, walk left past the red house unt...
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  • Schenectady, New York

    Plotter Kill Preserve Loop

    4.3
    6.14 mi / 860 ft gain
    There are a few entries into the preserve' however, this hike has you entering off of Mariaville Road. There is a kiosk here and you will enter on the Blue trail. Shortly after you can go out on the Blue trail to view the Upper and Lower Falls from lookouts above. From here, head northeast on ...
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  • Elka Park, New York

    Hike Twin Mountain

    6 mi / 1586 ft gain
    The DEC Parking lot, is located at the very end of a dead end, along Prediger Rd. Start at the trail head to the right of the trail kiosk and sign in sheet. The trail starts out very easy going as you approach the base of Twin. At mile 0.25, you’ll hit a junction where you’ll turn RIGHT towards T...
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  • Elka Park, New York

    Hike Indian Head Summit via Jimmy Dolan Notch Overlook

    4.9 mi / 1512 ft gain
    The view from the summit of this hike is incredible. Bring a sack lunch and a camera - you'll want to stay for a while! This trail is open for use year-round and provides great snowshoeing in the winter and fabulous wildflowers in the spring and summer. This is also a great location for birding!
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