John Hobby was born in England about 1632 [Prindle, Paul W., "Ancestry of Elizabeth Barrett Gillespie", Polyanthos, c. 1976, pg 208]. He died in Greenwich, Fairfield County, Connecticut sometime between April 24, 1707, when his will was written, and May 26, 1707, when his estate was probated [Fairfield Probate Records, pg 5:11]. His is referred to in court records as both John Hubby, John Hubbe, and John Hobbe.
John Hobby is first recorded on May 19, 1652 in Hartford, Connecticut in a court action where he failed to appear - his bond was ordered forfeited and he was held in contempt of court [Collections of the Connecticut Historical Society, pg: 22:109]. Winthrop noted a John Hobby in Massachusetts, most likely living in Dorchester, in 1637. This is probably a different person, or possibly his father [Winthrop, ii, 348].
By 1656, he was in Newtown, later Middleburg, Queens County, Long Island, New York. One of the Newton, L. I. records proves that he is the same person as the later John Hobby of Greenwich, Connecticut, and other entries prove the identity of his wife, Sarah Gray [Town Minutes of Newtown, 2:210].
He is first seen in the New Haven Colony in 1659 where he is the plaintiff in a case regarding owership of a horse [Hoadly, Charles J., "Records of the Colony or Jurisdiction of New Haven, 1653-1665", pg 141].
He was one of the original seven propieters of Greenwich, Connecticut. These included men from Wetherfield, who moved to Stamford, and then to Greenwich.
In the Greenwich Town Records for February 5, 1664/65, is an account of the first town meeting at which it was proposed to divide the "common lands by a rule of proportion, according to what each man's estate shall be visable..." The seven original proprietors were listed:

Jeffre Ferris, Senr.
Joshua Knapp, Senr.
Joseph Ferris
Jonathan Reynolds
Angell Heusted
John Mead, Senr.
John Hobbe.

On March 16, 1666, he was grnated that portion of the swamp that was adjacent to his property.
At the town meeting of May 6, 1669, a proposition was considered to purchase Mioschassiky from the few Indians still living about the western end of the town. Jonathan Reynolds, Sargent Lockwood, Goodman Heusted, John Hobby and John Mead were appointed to make a survey "of Horseneck and the lands thereabouts to find whether or no there can bee a suitable encouragement in point of land and other consideration for the settlement of a township."
The committee failed to complete the task due to the ill health of Jonathan Reynolds. A new Committee consisting of Sargent Lockwood, John Hobby, Joshua Knapp, John Reynolds and Mr. Hobby was reappointed.
On December 28, 1669, a committee was appointed consisting of Jonathan Reynolds, Sarg. Lockwood, John Hobby, Joshua Knapp, John Mead and Joseph Mead, to free the town of all claims by Daniel Patrick Jr. who appeared laying claim to his father's lands. The committee bought him off, paying a horse, saddle and bridle, and 50 pounds.
At the town meeting of February 6, 1670, the committee reported that the town had obtained the title to the Mioschassiky lands from the Indians. The land was laid out "to ye number of thirty lots, four acres to the homelot." These purchasers would be later called the "27 Proprietors of 1672." John Hobby was listed third. This area known as "Greenwich Old Towne", now Sound Beach, was first settled on the east side of the Myanos River. Horseneck, roughly what is now the modern city of Greenwich, Connecticut, was not settled until later. John Hobby is mentioned as "one of the original proprietors of Horse Neck" [Reynolds, M. T., "Reynolds Family, Stephen Reynolds Family", 1898. pg. 10].
On December 30, 1670, he was granted part of the uppermost meadows lying south of the Westchester Path.
In October of 1682, May of 1696, May of 1697, May of 1701, John Hobby served as Deputy to the General Court for Greenwich.
In 1686 and again in 1695, he served as a town auditor, appraising buildings, lands and estates.
On August 20, 1689, he sold land to Joseph Plamer.
In 1692, he was a member of the 12 men petit jury which tried the witchcraft case of Elizabeth Clawson and Mercy Desborough at Fairfield, Connecticut.
On December 14, 1693, he sold land to John Marshall.
In the tax year of 1694 to 1695, he is listed as having 94 pounds, and 15 shillings.
At the town meeting of February, 10, 1695/96, the record not that "Furder more, whereas there hath bin a Neglect in ye towne Conserning ye Entere of Thee Lands & fences belonging to hors neck and Coscob feild," "Mr. John Hubby," was appointted to a committee to "gaine ye best Ensite, by antient writtings, of Each mans propiete of Land in s'd feilds, with ye Quantitie of fence Layd to s'd Lands, & to methodise ye matter with what theye finde seutable to present to ye Towne at ye next Towne Meeting."
In 1696, he was appointed to a committee to help establish the boundary line between the towns of Stamford and Greenwich - "ye town Remaining Dissatisfied with ye Present setlement of Dividing line, do se Cause in order for a furder Tryall, & if it may be yt Love and pease may be Continued between Each town, Do hereby Make Choise on & appoint John Hobby, Dan. Smith & Sam'll Peck" to meet with such Stamford men as may be appointed, "to discorse ye matter...and make a Returne unto ye Towne..." [Greenwich Early Records: pg 103].
In 1698, John Hobby was appointed as a selectman. On January 11, 1703. He sold land to his son Benjamin. On October 17, 1707, there was an administrator's deed from the estate of John Hobby, to Corenelius Buncume.
During his service in Greenwich, he was also responsible for deciding upon fortifications for the town and obtaining amunition to protect themselves from Indians. He was also responsible for appointing persons to build a bridge, negotiating with "John Robyson concerning the building and seting up of a saw mill uppon byram River, also...to despose of as much land as may be necasary for John Robyson use," making arrangements for a horse pound and allowing John Whelply to build and operate a saw mill on the Mianus River. He also served on a committee to find someone to build a corn mill and later another saw mill. He was involved in the building of the meeting house and the church.

John Hobby married Sarah Gray in 1655 in Newtown, Queens County, Long Island, New York

They had the following children:

John ( - 12 Mar 1692/93) not married
Thomas ( - ) m. Rebecca _____
Elizabeth ( - 1750) m. Ebenezer Prindle
Martha ( - ) m1. Thomas Morehouse/Moris, Jr., m2. Abraham Adams
Rebecca ( - ) m. Samuel Hardy
Hannah ( - 15 Oct 1749) m1. John Green, Jr. m2. Cornelius Burnham/Bunkham
Mary (1670 - aft 3 Feb 1712/13) m1. Stephen Holmes, m2. Benjamin Green
Benjamin ( - bef 6 Nov 1744) not married
Rachel ( - ) m. Henry James
Jonathan ( - aft 1728) Sarah Mead

On June 24, 1699, John Hobby gave his daughter Hannah his negro, Harry, who was to receive "freedom from slavery after his own decease, only Harry to work five years for any master for 20 [pounds] which shall add to my estate for use of my sons, and to pay my father Hobby for boarding him" [Fairfield Deeds].
In his will of April 24, 1707, John hobby mentions sons Thomas, Benjamin and Jonathan; daughters Elizabeth Prindle, Hannah Bunkman, Martha Morehouse, Mary Holmes and Rachel James; daughters of his deceased daughter, Rebecca Hardy, - Rebecca and Hannah Hardy; his grandchildren John Hobby, Mary Holmes; and his son-in-law Stephen Holmes.
In a deed dated December 22, 1731, 'part of lot or right of land that was given by John Hobby of Greenwich, deceased, unto his daughter Mary and her children, and I, Sarah Renyalls, am one of the children of ye said Mary Holmes' [Greenwich Deeds, Vol. A, p. 131].