Croshaw is believed to be from the Crashaw family of Crawshawbooth, Lancashire, England; his parentage and date of birth are not known. He arrived in Jamestown, Virginia on the "Mary & Margrett", with the Second Supplyin September 1608. His wife came over on the "Bona Nova" in 1620 but, as she is not mentioned in 1623 Census, she was likely dead by 1623. He was a member of the Virginia Company of London in 1609 and was still listed as an adventurer in the Company in both 1618 and 1620. He was one of the authors of the complimentary verses prefixed to "The General History of Virginia, New England, and the Summer Isles" of John Smith of Jamestown. Croshaw and his wife had at least two sons, possibly three:
Joseph Croshaw, married 1. Unknown; 2. Widow Finch ; 3. Widow Anne Hodges; 4. Widow Margaret Tucker; 5. Widow Mary Bromfield
Noah Croshaw, married Elinor ________
Richard Croshaw, married Elizabeth _________
Raleigh Croshaw was the local official in the Elizabeth City area. This settlement later became known as the Middle Plantation and later Williamsburg, Virginia. His sons were among the first to take advantage of this new settlement. Both Joseph and Richard are mentioned many times in the records. Joseph appears to have led a more public life, having been a member of the House of Burgesses from York as well as having served as a justice and as sheriff for York County, Virginia.
Indian fighter
Croshaw was mentioned as being a member of the group with Captain John Smith in January 1609, who while attempting to trade for corn with the Indians at Opechancanough's village were almost overcome by surprise. This attack was thwarted in part by Raleigh Croshaw's quick reactions. Raleigh Croshaw then made a night trip back to Jamestown which helped to avoid further treachery. He appears to have been a very skilled Indian fighter. At the time of the massacre in March 1622, he was on a trading cruise on the Potomac. According to Captain John Smith's General History, Croshaw challenged the chief Opchanacanough or any of his warriors to fight him naked, an offer that was not accepted. When Captain John Smith published his General History in 1624, one of the verses in Volume III of the book had been written by Croshaw—and in his writing, John Smith implies a high opinion of Croshaw's knowledge of Indians and their way of making war. Raleigh Croshaw accompanied Claiborne on his explorations and, with just a few men, successfully defended a remote trading outpost up on the Potomac River in the 1622 attack. Captain Raleigh Croshaw was in the Potomac River trading in a small bark, commanded by Captain Spilman. There an Indian stole aboard and told them of the massacre, and that Opchanacanough had been practicing with his King and Country to betray them, which they refused to do, but that the Indians of Werowocomoco had undertaken it. Captain Spilman went there, but the Indians after seeing that his men were so vigilant and well armed, suspected that they had been discovered, therefore, to delude him, they gave him such good deals in trade, that his vessel was soon nearly overloaded".
Ancient Planter
About 1623 a patent was issued to "Captain Raleigh Croshaw, Gentleman, of Kiccoughtan, "An Ancient Planter who hath remained in this country 15 years complete and performed many a worthy service to the Colony," for 500 acres by Old Point Comfort. This was based on his transporting himself, his servant and his wife in addition to adventuring 25 pounds sterling in the Company. By the following year he was a burgess for Elizabeth City. In March 1624 he was issued a commission to trade with the Indians for corn. On this voyage he purchased a "great canoe" for 10,000 blue beads. The Corporation of Elizabeth City states that "Captain Raleigh Croshaw planted by Patent 500 acres between Fox Hill and the Pamunkey River to establish Elizabeth City." Captain Raleigh Croshaw was last referred to on November 22, 1624. On December 27, 1624, Captain Francis West was instructed to take an inventory of his estate. By 1637 the York County settlers had already begun to breach their own palisade and move into Indian land on the other side. The area between Queens Creek and Ware Creek was called the "Indian Fields." It was a series of vast communal fields the Indians used for planting corn. Again, it was Joseph Croshaw and Richard Croshaw who were the first to move into the area. In 1637 and 1638, they each patented a few thousand acres about where the Camp Peary government center is located today. They controlled most of the land in that area for the next 20–25 years.