Oldest Webster Family - The progenitor of the oldest, and probably the most numerous family in America, bearing the name of Webster, was John Webster of Warwickshire [believed to actually be Cossington], England. He came to the Massachusetts Bay Colony in a year not certainly known, but, by tradition, understood to have been about 1630-33. He removed from Newtowne, now Cambridge, Massachusetts, to the present site of Hartford, Connecticut, in 1636, presumably with the Rev. Thomas Hooker and his historic party.

Hartford, Connecticut - Hartford was then known by its Indian name, Suckiaug meaning "black earth," possibly from the dark rich soil of its fertile meadows and cultivated fields, portions of the country even then being under the rough tillage of the savages.

The South Side - John Webster located on the south side of Little River, a small stream flowing into the Connecticut from the west, and which, from the founding of the Colony, has divided the town into two unequal parts, the south side never quite equaling the north in population. In the beginning, it formed the boundary between two "plantations" into which the community was divided and this dual feature, with separate meetings, independent books, and recognition in the town votes, - continued even after the legal organization of the town was effected.

The North Side - The north side is the older. In the autumn of 1635, "about sixty men, women and little children, went by land toward Connecticut," says Winthrop's Journal, under date of Oct. 5, 1635, "with their cows, horses and swine, and after a tedious and difficult journey arrived safe there."

Colonial History - The Rev. William DeLoss Love, Ph.D., of Hartford, Conn., who is the author and publisher of "The Colonial History of Hartford" (1914), from which we are freely quoting, and hereby acknowledge our indebtedness, identifies the following as a part of that company, and thinks that they were the pioneers who located their house lots on the north side at that time, namely, Elder William Goodwin, John Steele, William Westwood, Thomas Scott, Stephen Hart, William Pantry, John Barnard, William Butler, William Kelsey, Nathaniel Ely, Nicholas Clark, Richard Webb, Richard Goodman, Edward Elmer, Mathew Marvin, Thomas Stanley,—sixteen.

He says, "in the judgment of the wise it was necessary for some to go forward to prepare the way, and there was at least a tacit agreement, to which the ministers were a party, that others would follow the next season."

To the above sixteen he thinks that nine more should be added, inasmuch as their house lots are intermingled with the others, as though they were all selected at one and the same time. Since, however, it is known that some, at least, of the nine, accompanied Hooker in his march the next summer, the author holds that, after selecting their lots in the autumn of 1635, they returned to Newtowne in time to accompany their families in their journey at that time through the wilderness to Suckiaug. The nine were Mathew Allyn, John Stone, Timothy Stanley, Edward Stebbins, James Olmsted, Robert Day, John Talcott, William Lewis, Clement Chapin. Two lots were reserved, - one each for Rev. Thomas Hooker and Rev. Samuel Stone.

But "the majority of the settlers who came in 1636, settled south of the river and became the South-Side Plantation." (Ibd.)

South Side Disputed Territory - The reason for this is not far to seek. The South Side was disputed territory. The Dutch claimed it. [The defect in the title to this land, in the view of the English, was, that it was obtained from the wrong Indians; the Pequots and not the Sequins who were the ancient owners.] They held their title from the Pequots, a powerful tribe who were already predatory and menacing, and with which, a year later, the English were to test their prowess. The English held their Indian titles from the Sequins, the ancient owners, who however, had recently been conquered by the Pequots and made tributary. Prudence would not permit the premature defiance of these forces, and hence the first lots were chosen on the north side; and the movement to the south side was delayed until the arrival, or the near approach, of Hooker, and the main body of his congregation.

Earliest South Side Lots - It is quite certain, however, that in the spring of 1636, after having secured rights through the Warwick patent lots were actually located on the south side, those of John White and Samuel Wakeman being the first including, possibly, that of William Hills. Having these titles, both from the Indians and the English, the settlers gave little heed to the Dutch fort called "House of Hope," and even before the arrival of Thomas Hooker and his band of pilgrims, boldly crossed the Little River and staked out their home lots as above shown. But on the arrival of the larger number under Hooker, in June, 1636, the majority of the new comers, either from policy or choice, or both, located on the south side. Among them were John Webster, William Whiting and Thomas Welles (the last from Saybrook) foremost men of the colony. Only five proprietors in the colony owned a larger share of the common, or undivided lands, than John Webster, and only one, William Whiting, as much. Of the seven largest owners of land held in common, four were located on the south side, namely, George Wyllys, Thomas Welles, John Webster, William Whiting.

Rev. Thomas Hooker's Journey - The journey of Rev. Thomas Hooker, and the main body of his faithful congregation, from Newtowne to Suckiaug will ever be memorable. Some had preceded them the autumn before; others early that spring, and probably a few followed later that same season. But the majority started from Newtowne, May 31, 1636, a hundred or more strong, including women and children. Mrs. Hooker, the pastor's wife, being too ill to walk, was carried on a horse litter. One hundred and sixty head of cattle were a part of the expedition, and furnished milk for the party. Thus encumbered, progress must have been very slow, and the journey required probably not less than ten days, and possibly more.

Hooker's Route - The route by which they reached Suckiaug has recently been established with probable accuracy. This was done in part by an exhaustive study of land records from Cambridge to Hartford, and noting the references to an ancient Indian trail which was no doubt the line of their march.

The course thus shown was from Cambridge to Watertown, Weston, Wayland, Framingham, passing north of Cochituate Pond; through the borders of South Framingham, Ashland, Hopkinton, Westborough, Grafton: thence through Millbury, north of Singleton Pond to Oxford, turning westward at the Centre, and going through Charlton, whose ancient name was "Quabaug Path." It is suggested that they spent their first sabbath at Sturbridge, on the western slope of Fisk Hill, where tradition locates a camping place. Going down the slope westward, and crossing the brook, they passed the foot of Cemetery Hill, and "Old Tantiusque Fordway," up the valley through Fiskdale. The path went north of Little Alum Pond to "Little Rest," and north of Sherman Pond and north of Steerage Rock, descending the slope to the Connecticut Valley at Agawan, now Springfield, Massachusetts.

From Agawam they moved southward on the east bank of the Connecticut River, through "Longmeadow Gate," so called because the shoulder of the hill and the river narrow the space at that point to something like a gateway, thence in a general line (still marked by highways), to what afterward was known as the "John Bissell ferry" at Windsor, where they crossed the river and completed their journey to Suckiaug on the west bank.

Governor Street - Whether John Webster and his family came in that group, or later in 1636, he located, as already shown; on the south side of the Little River, on what afterward was and still is known as Governor Street, not far from what became the famous Charter Oak. Governor Street was so named because of the number of men living in that vicinity who became governors,—Edward Hopkins, George Wyllys, Thomas Welles, John Webster, and as late as 1850, Thomas H. Seymour. The street extends from Little River, southward, crossing Sheldon Street at the head, and Charter Oak Avenue about midway of its total length. The street ends (1914) at Wyllys Street. On the east side of the street, about half way between Charter Oak Avenue and Wyllys Street, was the home lot of Gov. John Webster.

Webster Houses - In an interesting volume issued in 1900 by Isham and Brown of Providence, R. I., from the press of the Preston and Rounds Co. of Providence, entitled, "Early Connecticut Houses," Dr. Henry Barnard of Hartford, writes an important chapter in Appendix II, entitled, "The Webster Houses." His first effort is to correct the error that the houses on the estate of Lieut. Robert Webster, located on Retreat Avenue, and Washington Street were identical with the home of Gov. John Webster, father of Lieut. Robert Webster. Dr. Barnard says: "On this portion (Retreat Ave.) stand three houses, in none of which did his father, Gov. John Webster, ever live. Gov. Webster's home lot was on the same 'plot with Gov. Wyllys' (directly east of my residence) on the street now known as Governor Street, and the house, which I recollect as far back as 1817 when, I clambered over the fence to play with the Hilisdale boys, was always known as 'the Webster house.'"

Albert William Webster of New Haven, Conn., a descendant of Gov. Webster, issued in 1900, a twenty page pamphlet entitled, "One Branch of the Webster Family." In it, he explains that the Governor's home lot of two acres lay on the east side of Governor Street, and that the house in which the Governor lived was located on, or near the spot where the barn of Peter D. Stiliman, Esq., now (1900) stands.