Joseph Holley was born ca. 1605 in England and died at Sandwich, Massachusetts in 1647. He was probably a grantee of Dorchester, Massachusetts in 1634 and was certainly among the first settlers of Sandwich, ca 1637. He was a millwright and married Rose Allen, probably in England before emigrating to Dorchester ca. 1634. Rose was born ca. 1610 in England and died ca. 1693 in Sandwich. After Joseph's death she married William Newland. By 1657 he and Rose had adopted the Quaker faith, among the first in New England to do so, and Joseph's children were likely raised as Quakers. There were 23 Holway family members buried in the Sandwich Quaker Meeting House Cemetery between 1720 and 1884.
Not all researchers agree that the Joseph Holley who settled in Sandwich is the Joseph Holly found in Dorchester in 1634. Pope and Savage consider these to be the same man, while authors of the Great Migration Study Project do not. Their comment: "Inasmuch as six years separate this record [refers to a 16 April 1640 citation in Pope on a Joseph Hollyway in Sandwich] from the grant of land in Dorchester, and the surname in the early appearances at Sandwich is Holloway and not Holly, we do not agree with Pope."
We think Pope had this one right. Reliable sources place Joseph Holley at Sandwich in 1637, among the first settlers. Also, more than a dozen different spellings of this surname are found in records that can be reliably connected to this family, and early records of Sandwich show the name spelled Holway and Holley more often than Holloway. Pope's conclusion that the Dorchester Holly and Sandwich Holley are the same is supported by Dorchester town records showing that on 22 November 1634, John "Alline" and Joseph Holly, among others, had "six acres of land graunted them [for] their small and great lotts at Naponset betwixt the Indian field and the mill."
We think this reference is to Rose Allen's brother, John, and that they preceded their father, George Allen, who came to Massachusetts in May, 1635 with his second wife, Katherine, younger children (George, William and Mathew) and a servant (Edward Poole). George settled first in Weymouth, Massachusetts; but, like Joseph Holley and Rose, was among the first settlers of Sandwich in 1637.
Joseph and Rose had at least five children, but only one son that we know of, Joseph 2nd. Joseph 2nd married Mary Hull in Sandwich and remained there until his death in about 1691. Their children included five daughters and four sons; Joseph 3rd, John, Samuel and Benjamin. This generation is the first to be found most frequently as Holway in the records. Joseph 3rd remained in Sandwich and married Ann Jennings in about 1693. They had at least six children, including Joseph 4th. He removed to Dartmouth, married Hannah Soule, and by 1741 had settled in Dutchess County, New York. My family descends from this Joseph.
Joseph 3rd's brothers, John and Benjamin, removed to Rhode Island. It is not clear what became of Samuel. We have barely begun to research the Rhode Island branch of the family. Joseph 4th's brother Gideon remained in Sandwich where he married Experience Wing who bore him at least seven children, including Lodowick who removed to Machias, Maine; the first known member of this family to settle in that state. He was soon joined in Maine by three of his nephews, sons of his oldest brother, Joseph. By 1800, descendants of Joseph Holley and Rose Allen, with some variant of the Holley surname, can be found in Massachusetts, Maine, Rhode Island, New York, New Jersey, Maryland, Pennsylvania and Virginia.
As the number of family lines grew, so did the number of spellings of our surname. The 1790 federal census has 259 listings under seven variants of the Hawley surname and 110 listings under eight variants of Holloway. Of those, 190 lived in New England and another 43 in New York. None used the Holway spelling that was favored in other records from Sandwich, MA and in all subsequent censuses of Sandwich. I now understand why I almost always spell our name when asked for it at the Doctor's office or some other place where they must look up a record. We have recorded surnames in our database using the variant most commonly found for each generation. The original immigrant and his children are listed as Holley, the next two generations as Holway. After that, we've used the spelling most frequently found in records for that branch of the family.