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On his 13th birthday, Oakes became of age and became the sole owner of his family's land. He negotiated for roughly an eighth of it to remain church property, for a fee of £30 8 s 9 ½ d. His father had been a cattle farmer, but a period of frequent livestock thefts led Oakes to switch to cider. Even
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Fortunately for Oakes, because of his position as the only cider grower in
Bromyard, he enjoyed a profitable first summer and wiped out his debt. In 1460 he built a first tavern where his cider would be sold. It remained in family ownership until its destruction in the
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In 1467, he married 19-year-old
Elizabeth Francis, with whom he had five children. She died giving birth to the last one in 1479. A 1486 church document written to describe the changes in the town since the beginning of the rule of
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Oakes' date of birth is not known, but according to church records at St Peter's, Bromyard, he was baptised on 17 March 1442. His father, also called John, was slain the previous 19 September as the French recaptured
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with his gains from the sale to the church, he fell into debt during the long wait until the beginning of cultivation in August and the release of the first batch in June.
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mentions that Oakes died in that period, though it is unknown how he died or where he was buried. Richard, his only son to survive him, inherited his business.
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was among those the Oakes family owned. It is now used for its original purpose of cattle, while John Milton Oakes used it for growing cider.
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