Henry of Richmond appeared in 1483 off South Haven in a single ship which had been separated from the other vessels of his fleet by a storm, and he would doubtless have landed had it not been for the fact that Poole and Dorset men favourable to Richard held the shores against him. When, in after years, he succeeded in ascending the throne he appears to have remembered the action, and the town in consequence suffered from neglect during his reign.

In Henry VIII’s reign the Manor of Canford and with it the town of Poole were granted by the King to his natural son, Henry Fitzroy, Duke of Richmond and Somerset, and during this period a block house, which was afterwards superseded by a castle, was erected on Branksea or Brownsea. The town of Poole was responsible for the manning of the block house, but the King appears to have supplied weapons and ammunition.

In the reign of Elizabeth the place suffered very considerably on account of the insecurity of trade by sea; but, notwithstanding this fact, the number of ships belonging to the port about this time was upwards of twenty, ranging from fourteen to seventy tons. Of course, compared with the ships of the present day, even the largest seems insignificant, but it should be remembered that in those days a vessel of even fifty tons was considered large, and the one in which Drake circumnavigated the world was only twice that size.

Poole during the wars in the low countries undoubtedly took some part in the struggle which was going on there between the Dutch and the armies of Alva and Parma, and it is recorded that 300 soldiers raised in the west country were embarked from Poole. The town does not, however, appear to have taken any active part in the defeat of the Armada; probably the port was unable to supply big enough ships for Drake’s fleet, but there is little room for doubt that the privateers and merchantmen of the port helped the harrying of the Spanish ships when their formation had been broken up by the gallant attack of the fleet under Drake, Hawkins, and Frobisher.

During the Civil War Poole was on the side of Parliament, as was the whole county of Dorset, save Corfe Castle, Wareham, and a few isolated dwellings of Royalist gentry; and although at one time the King’s forces succeeded in dominating the county from one end to the other and holding all but the towns of Lyme Regis on the west and Poole on the east, the Royalists were ultimately overcome, but in consequence of the Poole malignants’ attitude Charles II, on his accession to the throne, caused the fortifications of the place to be razed to the ground.

Wareham, however, was a Royalist stronghold, and, in consequence of this, a Parliamentary ship was anchored off Poole Quay, so that it might assist in the guarding of the town and command the Hamworthy Road and Ferry, by which detachments of Royalist troops frequently came and went on their way to and from Wareham.

During the Civil War the town was visited by the plague, but in the reigns of Charles II and James II it appears to have progressed steadily if slowly. Its history, however, during that time is chiefly made up of the ordinary events of a seaport of the kind and does not contain anything of much note. The sympathies of the inhabitants during the Monmouth Rebellion were distinctly in favour of the duke and against James II, but, fortunately, as events turned out, Poole escaped the terrible retribution which visited all towns which had taken an active part in the ill-starred venture of the “Protestant” duke, and although, as in other towns, the heads and quarters of rebels hanged at Poole were set up as grim memorials, there is no reason to suppose that they were necessarily those of natives of the town.

In the last years of the seventeenth century the port became once more famous for the commercial enterprise and naval gallantry of its inhabitants. In 1694 one Captain Peter Jolliffe, the owner of a small vessel named the Sea Defender, witnessed the capture of a Weymouth fishing boat by a French privateer in Studland Bay. The gallant captain, regardless of odds, forthwith went boldly to the rescue, although the privateer was at least three times his strength and size, and not only made the freebooter abandon the prize, but evidently so harried him that he ran ashore near Lulworth, where the vessel was seized by the inhabitants and the crew made prisoners. Captain Jolliffe was presented with a handsome gold chain and medal from the King as a reward for his gallant exploit.

In the following year another Poole seaman, William Thompson, master of a fishing boat which was only manned by himself, one seaman, and a boy, attacked and captured a privateer sloop hailing from Cherbourg, carrying no less than twenty men, and brought her in triumph into the harbour.

One of the most romantic portions of the history of Poole during the last two centuries is connected with the many smugglers who dwelt in the town and neighbourhood. During that period smuggling formed the livelihood of many fishermen and seaboard dwellers along the whole of the south coast. Numerous attempts were made to put down the contraband trade in consequence of a petition presented to the House of Commons by legitimate traders, who stated in it that home manufacturers were greatly decayed by reason of the quantities of goods run, and entreated the House to attempt to deal with the evil. However, notwithstanding the many endeavours on the part of the navy and coastguards to suppress smuggling, the latter was in many parts of the county of Dorset so organized and carried on with such daring that all efforts to put it down were defied, and a state of absolute terrorism was created which affected not only the inhabitants of the neighbourhood where the smugglers carried on their operations, but even, to some extent, the men of the preventive service themselves.