Pittsfield, Massachusetts
Top Spots in and near Pittsfield
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Stockbridge, Massachusetts
You will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods.
You will reach a split in the trail, a left will take you...
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Adams, Massachusetts
When you reach the falls, you can cliff jump into a large swimming hole at the base. The best time to visit the falls is from April to November. Please note that dogs are not permitted here. Parking is at a cemetery, and the gates are open from 8am to 9pm. Use common sense before cliff jumping - ...
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Williamstown, Massachusetts
Park at the Junction of Sperry Rd and Rockwell Rd. To get to the trailhead, hike along Sperry Road for about 30 minutes. (Not to the end of the road, see map below.) Then hike along the March Cataract Trail, an out-and-back. You can bring dogs on leash. The trail is short but steep in some parts ...
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East Nassau, New York
5.0
1.62 mi
/ 308 ft gain
Kinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.
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Williamstown, Massachusetts
9.57 mi
/ 2849.96 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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Great Barrington, Massachusetts
At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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Great Barrington, Massachusetts
5.0
9.29 mi
/ 981 ft gain
Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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Savoy, Massachusetts
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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North Adams, Massachusetts
4.3
1.97 mi
/ 315 ft gain
The Cascades Trail is an out-and-back trail that takes you by a waterfall located near North Adams, Massachusetts.
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Hudson, New York
High Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.
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Sandisfield, Massachusetts
This swimming hole is 7-feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down.
Parking:
The swimming hole is located between Sandisfield Town Office and the post office. There is one dirt pull-off space near the swimming hole. The easiest parking is at the Town Offic...
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Cropseyville, New York
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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Mount Washington, Massachusetts
4.3
0.75 mi
/ 295 ft gain
Bash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers.
Parking Options
Massachusetts Side: 0...
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Sheffield, Massachusetts
4.0
2.47 mi
/ 1145 ft gain
Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
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Copake, New York
Bash Bish Falls from Taconic State Park is an out-and-back trail that takes you by a waterfall located near Copake, New York.
Swimming is not permitted at Bash Bish Falls.
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