This plantation took its name from its founder, Capt. Samuel Jordan and appears to have embraced 450 acres. At least in 1625 Jordan was credited with this amount as being "planted" by patent in "the territory of greate Weyanoke." It has been said that he established Jordan's Journey, also known as Beggar's Bush, in 1619 although in the Assembly of 1619 he represented "Charles Citty." He was one of the Assembly Committee of four appointed to examine "the first booke of the fower" of the "Greate Charter." In 1622 Jordan received a share of Company stock from Mary Tue as well as 100 acres in "Diggs his Hundred." At this time he was listed as "Samuel Jordan of Charles Hundred gentleman."
Jordan himself died in 1623 and his widow was soon seeking marriage again. When she became betrothed to two men at the same time, Capt. William Ferrar and Rev. Greville Pooley, and became embroiled in controversy, the Council took note of it. A proclamation followed which prohibited any woman from contracting herself to "two several men at the same time."
Jordan's Journey seems to have prospered. In 1624 Nathaniel Causey represented the plantation in the Assembly. At the time there were forty-two persons in residence and eight had died within the year. In 1625 the population stood at fifty-five persons (thirty-six males and nineteen females). Corn and fish supplies were adequate and there were some cattle and hogs as well as numerous poultry. In the matter of houses, the total was quite large—being twenty-two. The plantation boasted of three boats and substantial amounts of small arms (thirty-eight) and armor of various types (thirty-six items).
Captain John Woodleefe, a member of the Virginia Company, came to Virginia initially in 1609 and remained active and interested in the Colony. He was commissioned, in 1619, to go as governor and commander of Berkeley Hundred which he did late in the year. He had other interests, however, and by April of the same year had brought four men, which he had supplied with "apparell and armes," and his wife and children to Virginia. It is intimated that he had other colonizing interests and intentions. The Berkeley Hundred people had cautioned him about attempting another plantation that might interfere with their holdings. He was instructed not to establish it "unless full ten English miles from them."
He was governor at Berkeley Hundred for about a year and it was sometime shortly before, during, or just after this term of service, that he set up his own plantation. He seems to have chosen a point on the south side of the James a bit up river from Berkeley which he patented in 1620. It lay along the river and west of Jordan's Journey. This could very well have been the 350 acres listed in his name in May, 1625. His was one of the tracts in "the territory of greate Weyanoke" and was later patented again by his son.
This plantation appears in a listing in 1624. In March of that year, too, Isaac Chaplain represented it in the Assembly. This was another of the number of particular, or private, plantations founded in Virginia in the 1619-24 period. It is generally assumed to have been located in the area to the east of Woodleefe's Plantation. It was noted in May, 1625 that Isaac Chaplain had 200 acres which were "planted" in the "territory of great Weyonoke." He had as well, what may have been a personal stake, 50 other acres in the Corporation of Charles City.
In 1624 a total of twenty-four persons were living "At Chaplains choice" and a year later the head count stood at seventeen (thirteen males, four females). This 1625 figure, as did the other muster statistics, included the Truelove Company people and goods. This embraced two boats, but only two houses, forty-one barrels of corn and some small amounts of peas, meal and oatmeal plus three hogs and forty-eight fowl. There were reasonable amounts of small arms and armor and six pieces of ordnance. The latter, an unusually high figure for a private plantation, included one falconet and five "murderers." Some tobacco was being produced, for "John Trehern of Chaplins Choise" exported "one hogshead" in 1625. A lawsuit ensued when the ship captain sold it, although it had been consigned to Trehern's brother. As satisfaction he was to get "two hundred & thirty waight of tobacco in leafe & smothed together with one hogshead."