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During the 16th century locally produced wool was the major export commodity. Plymouth was the home port for successful maritime traders, among them Sir John Hawkins, who led England's first foray into the Atlantic slave trade, as well as Sir Francis Drake. According to legend, Drake insisted on completing his game of bowls on the Hoe before engaging the Spanish Armada in 1588. In 1620 the Pilgrim Fathers set sail for the New World from Plymouth, establishing Plymouth Colony the second English colony in what is now the United States of America.

During the English Civil War Plymouth sided with the Parliamentarians and was besieged for almost four years by the Royalists. The last major attack by the Royalist was by Sir Richard Grenville leading thousands of soldiers towards Plymouth, but they were defeated by the Plymothians. The civil war ended as a Parliamentary win, but monarchy was restored by King Charles II in 1649, who imprisoned many of the Parliamentary heroes on Drake's Island. Construction of the Royal Citadel began in 1665, after the Restoration; it was armed with cannon facing both out to sea and into the town, rumoured to be a reminder to residents not to oppose the Crown.

Throughout the 17th century Plymouth had gradually lost its pre-eminence as a trading port. By the mid-1600s commodities manufactured elsewhere in England cost too much to transport to Plymouth and the city had no means of processing sugar or tobacco imports, although it played a relatively small part in the Atlantic slave trade during the early 1700s. In 1690 the first dockyard, HMNB Devonport, opened on the banks of the Tamar and further docks were built in 1727, 1762 and 1793. In the 18th century new houses were built near the dock, called Plymouth Dock at the time, and a new town grew up. In 1712 there were 318 men employed and by 1733 it had grown to a population of 3,000 people.

Prior to the latter half of the 18th century grain, timber and then coal were the greatest imports. During this time the real source of wealth and the major employer in the region became the dockyard.The Three Towns conurbation of Plymouth, Stonehouse and Devonport enjoyed some prosperity during the late 18th and early 19th century and were enriched by a series of neo-classical urban developments designed by London architect John Foulston. Foulston was important for the town and was responsible for several grand public buildings, many now destroyed, including the Athenaeum, the Theatre Royal and Royal Hotel, and much of Union Street. Some of the greatest imports to Plymouth from the Americas and Europe during the latter half of the 19th century included maize, wheat, barley, sugar cane, guano, sodium nitrate and phosphate. Aside from the dockyard, other industries such as the gasworks, the railways and tramways and a number of small chemical works had begun to develop in the 19th century continuing into the 20th century. During the English Civil War Plymouth sided with the Parliamentarians and was besieged for almost four years by the Royalists. The last major attack by the Royalist was by Sir Richard Grenville leading thousands of soldiers towards Plymouth, but they were defeated by the Plymothians. In the 18th century new houses were built near the dock, called Plymouth Dock at the time, and a new town grew up. In 1712 there were 318 men employed and by 1733 it had grown to a population of 3,000 people.

Prior to the latter half of the 18th century grain, timber and then coal were the greatest imports. During this time the real source of wealth and the major employer in the region became the dockyard.The Three Towns conurbation of Plymouth, Stonehouse and Devonport enjoyed some prosperity during the late 18th and early 19th century and were enriched by a series of neo-classical urban developments designed by London architect John Foulston.