Henry Woodward came to New England in the James, Captain Taylor, Master. They left England 22 June 1635, having embarked at Bristol 23 May 1635. There were about 100 passengers on board, including the Rev. Richard Mather and Rev. Richard Denton. Although all the passengers were on board, the departure of the ship was delayed for a month, and after a voyage of 55 days they landed at Boston 17 August 1635. Two days before they landed, there was an extremely severe storm. The James lay anchored off the Isles of Shoals and the "Angel Gabriel", which had accompanied the "James" for about two weeks, became separated, and was off the coast of Pemaquid ME when the great storm of Aug 15 struck. The James was torn from her anchors and put out to sea, but after two days of battling wind and wave she reached the harbor with "her sails rent in sunder, and split in pieces, as if they had been rotten ragges." The "Angel Gabriel" was a total wreck and several lives were lost. Rev. Richard Mather, a passenger on the James, kept a diary of the trip.
On 18 October 1659 the General Court of Boston made a grant to Dorchester, and on 14 November the selectmen of Dorchester "impowered William Clarke and Henry Woodward to serch and stake out a Farme of 1000 acres of land ... for the use of a scoole... " On 10 Nov 1659, Henry Woodward, husbandman of Dorchester, deeded 8 acres of land at Dorchester to William Sumner for L14. Roger Clapp witnessed the deed, and it was acknowledged by Henry and his wife Elizabeth four days later.
Henry Woodward, William Clark and Henry Cunliffe had received generous grants of land in Northampton in June 1959, and now the three families removed to Northampton.
The journey was 2/3 the length of the state, a formidable undertaking. An account of the Clarke family's trip says: "He moved his family to Northampton in 1659. His wife rode on horseback with two baskets called panniers slung across the horse, carrying one boy in each basket and one in her lap, her husband, fifty years old, proceeding on foot." Clarke and Woodward received 12 acre homelots, larger than those enjoyed by any of the other residents, and 100 acres of meadow apiece besides. This reflects their standing in the community. It is said that they, and four others who came about the same time, "brought new life and energy to the enfeebled town.
Henry and others were dismissed from the Dorchester Church 28 Feb 1661 to join the others forming a church at Northampton. Wife Elizabeth was dismissed into the Northampton Church 1 July 1661. Though there had been regular church services, there was no religious organization in Northampton until June 1661 when Rev. Eleazer Mather was ordained, and a church organization set up. The original seven male members, with the Rev. Mr. Mather, were called the "Pillars of the Church." The term seems to have been complimentary and honorary here, rather than official as it was in the New Haven Colony.
In 1663 the Hampshire Troop of Horse was formed, and Henry was chosen its quartermaster. "A troop of horse was not to exceed 70 soldiers. Each trooper was to have a good horse, saddle, bridle, holsters, pistol or carbine and a sword. A troop had a Captain, Lieutenant, Cornet, Quartermaster, Clark, Trumpeter and Corporals. Each trooper was obliged to keep a good horse at all times and was allowed by the Colony 5s a year." The Hampshire troop was permitted to be organized temporarily with 36 men enrolled.
In 1665 Henry was given permission to keep an ordinary to well wines and liquor and entertain the Court which met in the town, probably in his tavern. He continued as tavern-keeper until 1681, and during this time he regularly "entertained the court" which sat each year in Northampton. On 4 November 1668 Henry and John Woodward were among those who signed the petition to the General Court protesting against imposts. In 1672/73 he contributed 8 pounds of flax to Harvard College. He and his son took the oath of allegiance that same year. He was several times a Commissioner, frequently a selectman and a constable, and a member of the first and subsequent tithing-boards.
Early church discipline appointed certain men to see that Sunday disturbers were properly punished. They were to attend to any disorder in the congregation or near the meeting house, and had certain responsibility for family life and morals in the neighborhood. In Northampton in 1678, when Henry Woodward was appointed, they were first called tithing-men. His status was "elective, patriarchial headship over a neighborhood of at least ten families' and included regulating the Sunday congregation and preventing mischievous boys and girls from making a disturbance. 'He tapped the whispering urchin on the head, jogged the snoring deacon, tortured the ear of the somnolent female, or if the culprit was too distant, rapped sharply on the pew rail, pointing his black rod at the offender' for 'The law required the tithing-man to have a 'black staffe' two feet long, tipped at one end with brass about three inches as a badge of his office." In earlier times it is said that the "tithing-man's rod was tipped at one end, not with brass, but with a squirrel's tail. This end was used in awakening women. The other end was fitted with a deer's hoof, which carried sharp conviction to men and boys." Frequently two or three tithing-men served at a time. Usually one "at each door of the mtng hs to keep out dogs & often one sat in the gallery to keep in boys." "They were not merely to preserve order in the meeting but also to see to it that every one went to church."
Henry was killed on 7 April 1685 "at the upper grist mill"; the cause of death is given as a stroke of lightning and as an injury by the mill wheel.