John Wolcott, c. 1547-1623, was the miller at Tolland, as his father had been before him. The court books of Taunton Deane record the name of John Wolcott or Wulcott as miller at Tolland from 1585 until 1603, and show that he was elected tithingman for Tolland for 1585/6. After 1603 the names of Henry Wolcott and John Wolcott alternate as miller until 1636. The mill was part of the property that John's son, Christopher, purchased freehold in 1618. John's other son, John, operated the mill after Henry, emigrated to America in 1630. "John Wolcot and Agnes Crosse al. Aishe" were married at Lydiard St. Lawrence in 1579. Agnes may have been a widow, and Ash the name of her first husband. The will of Thomas Crosse of Tolland, husbandman, dated 1583, requests that "his good friend" John Woolcot be one of his overseers. The will of Francis Crosse of Tolland, dated 23 January 1588 also has John Woolcott as overseer, and John and Henry Wolcott as witnesses. These men must have been Agnes' relatives, and they were all probably related to Walter Crosse, AB, who was the Tolland parish priest from 1480 to 1517, and John Crosse, AM, who was the Tolland parish priest from 1517 to 1554. John Crosse was replaced as rector at Tolland in 1554 when about one fifth of the parish priests in England were replaced by order of Queen Mary, most of them because they were married. Agnes Crosse, wife of John Wolcott, may have been John Crosse's grandaughter. A John Crosse of Tolland left a will dated 1544 which was proved at Taunton, but has since been destroyed. Another member of the Crosse family, William Crosse, was rector at Stawley, a village 5 miles south of Wivilscomb, from 1515 until his death there in 1531. Henry Howe of Stawley, who died in 1528, left a bequest to William Crosse, his curate, and the will was witnessed by John Crosse, parson, probably the rector of Tolland.
In 1592, John Woollcott of Tolland was executor of the will of Robert Goodgrome of Nettlecombe, his brother-in-law. Robert left 40shillings to his sister, Avis Denborowe, and 20 shillings to each of her 3 children; 30shillings to his sister Agnes Cross; 20s to each child of his brother-in-law Thomas Duddridge 20 shillings each to the 4 children of John Woollcott, and the remainder to John. Another will, that of Walter Washer of Lydiard St. Lawrence, dated September 1592, has John Wolcott as overseer. He is probably the John Woolcott involved in a dispute with the rector of Lydeard St. Lawrence in 1607. Witness testified that John had owned three or four acres in Lydiard St. Lawrence for ten years, which he, his son, and servants and laborers used "for tiling or healing stones to cover houses." He had kept two, three, or four horses or mares " to carry his heling or tyling stones to be sold," sometimes at Tolland and sometimes at Brompton Ralph. In 1612, John Woolcott of Tolland, husbandman, made a deposition on behalf of Robert Sellack of Tolland. He said he had lived at Tolland for about 50 years, and before that at Elworthy since infancy, and that he was born at Tolland and was age 65 or thereabouts (b. c. 1547). His son, John Woollcott, junior, of Tolland, yeoman, also testified, saying he was age 30 of thereabouts and had lived at Tolland since birth.
John's will, dated and proved in 1623, leaves household items and 5 shillings 8 pence to Hugh, Agnes, and Mary, children of his son, John; 6 shillings 8 pence to each child of his son, Henry; 2 shillings 6 pence to "Symon Wolcott my kinsman now dwelinge wth me"; 2 shillings 6 pence to his servant, Giles More; 7 pence each to Richard Locke and Alexander Shattuck; 12 pence to John Sealey; 2 shillings to Maudlen Engram; and the remainder to his son, Johni; with Christopher and Henry Woolcot as witnesses.
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