In 1638, after six weeks of a tempestuous sea and storm voyage, Obadiah Holmes, Sr., his wife and 3 year old son Jonathan, arrived in Boston Harbor and settled in Salem. He and his wife were admitted to the First Church of Salem the following year. He went into the glass business with two other settlers. Life appeared to be pretty good for Obadiah and his family.
Young Obadiah thought deeply about his religious beliefs and may have been disturbed and disappointed by the rigidity he found in the New World. He was not afraid to express his dissent about some doctrines and practices of the established Church. He may have even enjoyed it. Dissent, however, was not long accepted or tolerated by the authorities so Obadiah began to look for a new place to settle.
On 1 January 1644, Obadiah drew lot 37 in a division of land at Rehoboth in the Plymouth Colony, 60 miles east of Salem. He sold his holdings in Salem by 1645, removing himself and his family to Rehoboth the same year. He became a member of Reverend Samuel Newman's church and was elevated to the status of freeman in 1648, but his religious views placed him in conflict with Newman. In 1649 Obadiah took Newman to court for slander, setting damages at 100 pounds. Newman had accused Obadiah of taking false oath in court, but later admitted doing this based on the claims of others rather than his own knowledge. When Newman admitted his error, Obadiah won vindication, but peace for Obadiah was short lived.
He became the leader of a small faction within the church, known as the "Schismatists," and by 1650 he and eight others had separated from the church and were baptized, with Holmes becoming their pastor. On 12 June 1650, Rev. Newman obtained an order from the Grand Jury at New Plymouth that forbade Obadiah and his followers from holding religious meetings in their homes. Obadiah and his follower disobeyed this order.
On 2 October of that year Obadiah and several others were indicted by the Grand Jury for "continuing of meeting upon the Lord's Day from house to house, contrary to order of this court." Members of the court indicting Holmes included Governor William Bradford, Captain Myles Standish and John Alden.
As a consequence of the court action, he and the others left Rehoboth to settle in Newport in the Colony of Rhode Island and Providence Plantations.
In Newport, Holmes became associated with John Clarke and John Crandall, and with the Newport church. In 1651, the three men left Newport to visit, encourage, and minister to their Baptist friends in the vicinity of Lynn, Massachusetts. On Sunday, 21 May, they were holding a church service for several neighbors in the home of William Witter, a blind and invalid friend. While Mr. Clarke was preaching to Witter and a small group assembled at his house, two constables broke in and arrested the three men. They were charged with worshipping God according to the dictates of their own consciences and not in places and according to the prescriptions and forms of the civil law regulating the worship in that was called the established Church. Their views on the subject of baptism were regarded as heretical. Obadiah did not accept restrictions on the worship of God, nor the validity of infant baptism, believing that each person needed to individually decide to be baptized. For these beliefs, Obadiah, Clarke and Crandell, were accused of not accepting the validity of the established Church.
The arresting officers had them imprisoned in Boston the following day. One week later their trial began, with the members of the court being Governor John Endecott, Deputy Governor Thomas Dudley, Richard Bellingham, William Hibbins, and Increase Nowell. The guilt of the defendants was assumed and any defense on their part was stifled. Even the Reverend John Cotton weighed in with denunciation for the prisoners and the Reverend John Wilson struck a blow to Obadiah while he was supposedly in the protection of the court.
The result of the trial was that Obadiah was fined 30 pounds, Clarke was fined 20, and Crandall five. Clarke protested their heavy fines and Governor John Endecott replied that Clarke "deserved death" and "was worthy to be hanged." They were recommitted to the common jail. Friends quickly raised the money to pay the fines for Clarke and Crandall and they were soon released. As the fine on Obadiah was heavier, it took longer to raise, but his friends were ready to pay it. When Obadiah discovered what was happening, he forbade the payment of his fine, as a matter of conscience.
Efforts were made to induce him to recant, at least, so far that the corporal punishment might be avoided. He refused.
On 5 September 1651 a crowd gathered around the whipping post in Boston to watch the flogging. Obadiah was taken to the town's whipping post and asked to speak, but Magistrate Increase Nowell refused. Obadiah spoke anyway.
"I am to suffer for...the Word of God and testimony of Jesus Christ," he said.
"No, it is for your error and going about to seduce the people," replied Nowell.
The two men continued to debate as the executioner removed Obadiah's shirt. He was then tied to the post and given 30 lashes with a three-corded whip held in both hands and laid on slowly with all the strength of the officer. Blood was said to have saturated his trousers and to have run into his socks. He was said to have not groaned once during this punishment.
In 1651, an open wound, as would be caused by whipping, was subject to infection and, in that day, an infection often led to death.
Writing later about the event, Obadiah related "...having joyfulness in my heart, and cheerfulness in my countenance...I told the magistrates, 'You have struck me as with roses.'" While he claimed to have felt no pain during the incident, he was so cruelly whipped that his companion, Dr. Clarke, wrote, "that in many days, if not some weeks, he could take no rest, but as he lay upon his knees and elbows, not being able to suffer any part of his body to touch the bed whereon he lay." Much later, Rhode Island's Governor Joseph Jenckes wrote, "Those who have seen the scars on Mr. Holmes' back (which the old man was wont to call the marks of the Lord Jesus), have expressed a wonder that he should live."
The authorities issued a new warrant to re-arrest Holmes, but his friends "defeated the purpose...by spiriting him away." Shortly after the incident, Roger Williams wrote a letter to Governor Endecott, making an earnest plea for toleration in matters of conscience and religion, but the letter failed to accomplish its objective. Obadiah returned to Newport and when Dr. Clarke left for England in late 1651, Obadiah succeeded him as minister of the First Baptist Church in Newport, and he held this position continuously (sharing the position when Clarke returned) until his death 30 years later.
In 1665, Obadiah was one of 12 persons named in a patent from the Duke of York for the Monmouth grant in East Jersey, which encompassed parts of Monmouth, Middlesex and Ocean Counties. The date of the patent was 8 April 1665, and while Obadiah never lived there, some of his children did settle in this area.
Obadiah was so highly regarded in the Rhode Island colony, that during the devastation of King Phillips War in 1676, the General Court put out a request for the "advice and concurrence of the most judicious inhabitants" of the colony. Among the 16 prominent Rhode Islanders named was Obadiah Holmes.
Obadiah wrote his will on 9 April 1682, with Edward Thurston and Weston Clarke (son of Governor Jeremy Clarke as witnesses. He died six months later, on 15 October, and was buried in his own field where his grave marker still stands. This Holmes burial ground, originally in the town of Newport, is now within the town of Middletown, Rhode Island.