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Check out franklin park, same area as franklin park zoo in Ma. Usually there is a great horned there in the pines on the golf coarse. I personally have not seen one yet there, but I do not go there alot.
Also, in Daniel Webster Sanctuary in Marshfield, Ma. There are long earred owls there,I have not seen reports yet if they are there, but usually they are there every year. I have seen them on a few occasions. As many as 5. They are tuff too get photos of.
See if any local groups are doing Owl walks, you will learn some areas they hang out in.
PS, you may need a 500mm for the reach