He was a follower of the Puritans from an early age, and emigrated to Plymouth Colony with his sister in July 1623 aboard the Anne.
John Lyford came to America and was welcomed at first, but soon Plymouth residents gravitated to him who did not share the Puritans' viewpoints.
Oldham was a supporter of Lyford, and the two of them stirred up dissension and trouble in Plymouth, according to the accounts of Pilgrim leader William Bradford.
Oldham next refused to stand his scheduled watch (a communal duty expected of all the men) and began to be insolent to the Pilgrims' military advisor Miles Standish.
Lyford and Oldham were put on trial for "plotting against them and disturbing their peace, both in respects of their civil and church state," and they were banished from Plymouth.
[citation needed] As a trader, Captain Oldham sailed to Virginia and England, but by 1630 he was back in the Massachusetts Bay Colony.