Just came back from a great walking tour of Dogtown, Gloucester with Walk the Words Tours (walkthewords.com). I never would have found the cool boulders, eerie cellar holes or learned the history of this fascinating area. I also probably would have gotten lost, because that place is huge. I took the 2.5 Babson Boulder tour (they offer another that goes to Whale's Jaw) and Seania McCarthy knows her stuff. Highly recommended.
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