 In 1607 , after a voyage of 144 days , three ships headed by Captain Christopher Newport , and carrying 105 men and boys , made their first landfall in the New World on the mainland , where the southern mouth of the Chesapeake Bay meets the Atlantic Ocean . They named it Cape Henry , after Henry Frederick , Prince of Wales , the eldest son of King James I of England . These English colonists of the Virginia Company of London moved on from this area , as they were under orders to seek a site further inland , which would be more sheltered from ships of competing European countries . They created their first permanent settlement on the north side of the James River at Jamestown . 
