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Ancestral File says that Thomas and his wife were probably born and married in England. If so, they probably landed at Boston, did not stay there long, and moved inland. In Genealogy Forum I have seen a statement that these Websters are related to the Websters of New Hampshire (Daniel Webster's line). If so, there seems to be a generation gap that makes linkage problematical.
Thomas was born ca. 1723 (his wife in 1725), which was not a time of much immigration to New England, and what there was came mostly from Ireland (mainly Ulster Scots, although some of the colonists of the Ulster plantation were English). He is not likely to be any of the persons named as an immigrant "Thomas Webster" in Coldham's various Passenger Lists (the dates of transportation don't work well]. People who wanted land would usually go to Pennsylvania or Virginia if they had any choice in the matter and wanted cheap land, which was what most people wanted. Why would he choose Upton (having lived previously for brief periods in Sutton and Uxbridge)? One clue may lie in his religion. Two of his sons, Jonathan, a lay minister, and Samuel, a minister, were Baptists. Joseph Carpenter, a collateral ancestor of Jonathan's father-in-law in Dudley, also called Joseph Carpenter, was a founder of the Baptist church at Rehoboth. Although there do not seem to have been any Websters in that congregation at an early date. But there were two persons named Webster, William Jr. in 1746, and Benjamin in 1759, who died in Dudley, where a Baptist congregation had been active since 1744 if not earlier. Dudley is the town where we find the earliest probate records of Worcester County. So I think there is a reasonable chance that Thomas Webster was in Dudley before he went to Sutton, where there was another Baptist church that had been active from an even earlier date (1735). He was obviously a poor man, being warned out of Upton in 1750. So he could afford to be a non-conformist where a respectable man in the community with a position to protect would tend to be staunchly puritan. There were Websters at Richmond/Westerly, RI, and at various places in Connecticut. In fact, the naming customs in Thomas's family, using names like Jonathan, Benjamin, Samuel, and Mehitable, much resemble the names used among some of the descendants of Connecticut Governor John Webster. These names occur in other Webster families too, of course, but it is the grouping of the names that is distinctive in the Connecticut family. (N.B. Lists of children vary a little, and there may be no birth records for children born outside of the Connecticut towns where the Websters first settled.)
For example, Robert Webster (son of Governor John) had sons named Jonathan, Samuel, Benjamin and William. The first three names are also given to children of Thomas of Upton, and the last one appears in Dudley probate records. Robert had a brother named William who moved to Hadley, MA. No children are listed for this William (his known wife, accused as a witch but acquitted, was probably a second wife). Jonathan Webster (son of Jonathan, son of Robert, son of John) 1681-1758, had children named Jonathan, Mehitabel, and David, and possibly Benjamin, the same names given to three or four of the six children of Thomas Webster of Upton. Supposedly all of these people died in Hartford or Middletown, but I wonder. Two sons of Jonathan, son of Robert, are Samuel and Daniel. There does not appear to be any info about their descendants, if any. This is unfortunate because the name "Samuel" is a good prospect for the line we are seeking to establish. Those Websters who moved to Lebanon, CT, would be in the best geographical position to make a northward move to the vicinity of Dudley, although Middletown is not much farther away, and even Hartford is not too bad as long as one does not mind going diagonally across a lot of streams to get there. The Websters moving to Hadley (ex-Governor John and three of his sons) did so because they disagreed with the plan of the incoming pastor to liberalized the rules for baptizing children. The causes of dissent might vary from generation to generation, but the principle of dissent itself was well established in this family. If William (son of Governor John) had children they may have soured on the puritan church after seeing how it treated their step-mother. Without more evidence, however, this is all speculation.
The family of John Webster (d. 1783), settled originally at Boston, and eventually at Westerly, RI, at the mouth of a natural route of migration that starts at the coast and moves north through eastern Connecticut ending near Dudley. The route starts out either following a number of smaller streams to the Quinebaug, or one could travel west along the coast to New London and then stay on (or at least alongside) water all the way north to Dudley township. John Webster had sons named James, John, and Thomas, and Thomas had a son named Jonathan, but the ages and places of death for this family group do not seem to fit well for purposes of a link to the Thomas of Upton. There was a Baptist church at Richmond, where they lived for a time. In fact, the first Baptist church in Connecticut was established at Groton on the east side of the bay from New London (on the west side) about 1704, not far from Westerly, RI.
But it was the "New LIght" movement from 1740-1760 that began the rapid growth of the Baptist denomination. Most likely Thomas Webster did not adhere to the Baptist faith, if he ever did, prior to that period. It is his sons, Jonathan and Samuel, who are known to be Baptists. There is no information available about Thomas's own beliefs.
Pvt. Thomas Webster served three months and seven days, 200 miles from home at West Point, as part of a callup of troops to assist the Continental Army. Webster and others from Upton supplied their own firelocks for this service. Webster was stationed there during the infamous command of Benedict Arnold, who had planned to betray the fortifications to the British army. Arnold barely escaped capture on Sept. 26, 1780. If Arnold had succeeded, Webster and those serving with him would most likely have ended up as prisoners of war. The records do not give the soldier's age, but as his son of the same name was only 14 at this time I have assumed that the record refers to the father rather than to the son. No pension application in his name was ever filed, which would have been a lot more likely if it was the son who had served. But if this assumption is incorrect, then the son served at a very early age, much younger than most.
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