1585 – He was born this year in Norfolk, England. At the time, Spain held a virtual monopoly on the lucrative tobacco trade within Europe. Most Spanish colonies in the New World were located in southern climates more favorable to tobacco growth than the English settlements.
1607 – Jamestown had been established by an initial group of settlers in this year.
1608 – After two return trips with supplies by Christopher Newport arrived in this year, another relief fleet was dispatched in 1609, carrying new settlers and supplies across the Atlantic. This "Third Supply" fleet was broken apart by a severe hurricane.
1610 – The two newly-constructed ships set sail from Bermuda, with 142 castaways on board, including Rolfe, Admiral Somers, Stephen Hopkins and Sir Thomas Gates.
1612 – After his wife and child were buried in Bermuda, this year, he established Varina Farms, a plantation on the James River about 30 miles upstream from the Jamestown Settlement.
1614 – He married Pocahontas, daughter of the local Native American leader Chief Powhatan. Chief Powhatan gave the newlyweds property that included a small brick house just across the James River from Jamestown which was used as a home or cottage by Pocahontas and John Rolfe when they were first married.
1616 – He and his wife traveled to England in 1616 with their baby son, where the young woman was widely received as visiting royalty. However, just as they were preparing to return to Virginia, she became ill and died.
1622 – He died this year, but it is unknown in what manner. He may have been killed by the Powhatan Confederacy during the Indian Massacre of 1622, or at another time during that year of warfare between the colonists and the tribes.