There is no evidence of a Roman settlement on the present location of the town of Whitehaven, even though there was a Roman Fort 1 . 2 Miles away from the town. The area was settled by Irish-Norse Vikings in the 10th Century. The area name is Copeland and includes whitehaven. This indicates the land was purchased from the Kingdom of Strathclyde more than likely purchased from loot stolen from Ireland. 

The Priory of St. Bees owned the village of Whitehaven until Henry VIII dissolved the monasteries in 1539. The town was largely created by the Lowther family in the 17th Century. In 1630 Sir Christopher Lowther purchased the estate and used Whitehaven to export Coal from the Cumbrian Coalfield, mainly to Ireland. In 1634 he built a stone pier where ships could load and unload cargo. 

In the 18th and the 19th centuries Whitehaven grew into a huge coal mining town and also became a big commercial port with Daniel Defoe visiting in the 1720's. John Paul Jones Led a Naval Raid on the town in 1778 during the American war of Independence. The town had links to many famous people including Mildred Gale grandmother of George Washington and William Wordsworth who often came into the town to visit family.

Because of Whitehavens well planned layout in a right angled grid there is many speculations by historians that whitehaven was the blueprint for the New York City street grid system.

Whitehaven castle was built in 1769, which replaced an earlier building destroyed by fire. In 1924 the earl of Lonsdale sold Whitehaven castle to Mr H. Walker, who then donated the building to the people of Cumbria, along with monies to convert it into a Hospital to replace the Victorian Whitehaven Hospital. When the new West Cumberland Hospital opened in 1964 the castle was turned into a Geriatric unit but was forced to close in 1986 , because of fire regulations. It has now been converted into private housing.