Most who came here were doing so for some reason related to freedom, whether of a political, religious, economic, or other nature. From the time of Henry's arrival here (1634) until the time of George III (reign started in 1760), there were twelve changes in structure in England due to several factors, such as civil war, including the four periods non-royal administration. In other words, things were unsettled.
Our effort at freedom was a continuation, in a sense. The descendants chafed that their rights would be reigned in after the long time of mostly self-administration. I say 'mostly' in that the England, for the most part, decided who was in charge, even with elections.
It might be interesting to look at Henry's descendants and their lives, in relation to the status in England. Given that we're in July, the theme of Independence might be a good start.
Who better than Col Pickering to start with? He was a descendant of Mary (Lunt) Wingate who was a grand-daughter of Henry. Mary's daughter was Timothy's mother.
Timothy was too young to have participated in the French & Indian Wars. So, he was not involved with a conflict under the Crown.
He got out of Harvard in 1763. That is about the time that the 'shadow' governmental efforts, such as the Committee of Safety, were kicking off. Timothy was drilling the Essex County militia; what would have been his opinion of those pushing to remove themselves from British ties?
The Biographical Directory of the United States Congress says that Col Timothy was on a Committee of State of Rights of Colonists in 1773. During the war he served under General Washington as adjutant general.
After the war, Col Timothy held many positions under Presidents Washington and Adams. He also held political positions.
During the period of the War of 1812, Col Timothy seemed to lean more to England than France. He was involved with an effort that wanted New England to be a separate entity.