I'm not related to the Prest family, but I can answer some of your questions.
Eliza and Homer Sargent were brother and sister. She married Edward Prest from Hingham, MA. They had a daughter named Harriet, who may have been called Hattie. The Sargents were prominent in Leicester, Ma. Cherry Valley is a section of Leicester.
The Sargents were in the card clothing industry. Those are the wooden paddles used to straighten wool when preparing it for weaving. Leicester produced 2/3 of all the cards used in the country at that time.
The other town you mentioned in MA is spelled Whitinsville and is near Leicester.
I'm very much interested in history in general and particularly in the history of my town. I'm the current President of the Leicester Historical Society. I'd very much like to see the letters you spoke of. If I can help with any other information, please let me know.
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