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Great Barrington

The Top 8 Attractions around Great Barrington

There are plenty of places to see and visit around Great Barrington. Whether you love hiking or cycling, Great Barrington is a region where 8

hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.

Last updated: November 27, 2025

Benedict Pond

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Benedict Pond was once part of the Civilian Conversation Corps (CCC) construction project. This included building an earth dam to create the approximately 14-acre Benedict Pond.

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Monument Mountain (nature reserve)

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Monument Mountain is a nature reserve in Great Barrington, Massachusetts, is a geological home for different rocks and minerals that are natural to the area. There are a number of …

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The Ledges

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If you parked and started at Benedict Pond and follow the loop counter-clockwise you will encounter stone steps, boulders and a large beaver swamp on the way up to "the …

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Elizabeth Freeman Monument

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Elisabeth Freeman was the first slave to be freed by the court. Her case ended slavery in Massachusetts.

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Jug End

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At Jug End, the trees give a wonderful view over the woods and neighboring mountains to the northwest and southeast.

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Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

CheshireAdamsPittsfieldWilliamstownNorth AdamsLenoxLeeLenox DaleHousatonic

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