Deal is first mentioned as a village in the Domesday book, but archaeological evidence suggests it was settled as early as the first Roman invasion by Julius Caesar in 55 BC. Deal remained a small fishing village until 1228 when the town was named a 'limb port' to the Cinque Ports, Hastings, Sandwich, Dover, Romney and Hythe. From the French word "cinque" meaning five, the Cinque Ports were part of the countries defences from the 11th century, and their purpose was the production of warships for England's Navy. This new status allowed Deal to grow into one of the busiest ports in England during the medieval period, a peculiarity, as it does not have a traditional harbour. The water between the town and Goodwin Sands, called The Downs, provided a naturally sheltered anchorage for large vessels, merchant ships and the Royal Navy. Small tenders piloted by local watermen known as Luggers transferred their goods and crews back and forth to docks on shore. Admiral Lord Nelson was a regular visitor to the town and Deal was the first English soil on which James Cook set foot in 1771 upon returning from his first voyage to Australia. At times, there would be hundreds of ships anchored off the coast, bringing an enormous amount of prosperity to the area.

In the early 1500s, tensions were on the rise between England, France and Spain. It was then, as part of Kent's defences, Henry III commissioned the construction of three castles in and around Deal.
Two remain and are open to the public: one in the town and the other a few miles down the coast at Walmer. Their rounded walls were designed to resist the latest weapon of war, the cannon.
Walmer was for sometime the official residence of the Lord of the Cinque Ports. Perhaps the most famous Lord was Arthur Wellesley, the Duke of Wellington. Interestingly, the chambers he used are actually preserved as they were from the time of his death. The castle exhibits a significant amount of Wellington memorabilia and personal belongings, including a pair of his Wellington Boots.

In 1672 a naval yard was built in the town with repair facilities and storehouses covering 5 acres of land. This again boosted the importance of Deal. With the increase in trade, came an increase in crime and the town became infamous for smuggling. It reached such a pitch in January 1784 that the then Prime Minister William Pitt, suspecting many of the Deal luggers to be involved, sent a regiment of soldiers to Deal to smash and burn their craft. The irrepressible spirit of the Deal boatmen remained undaunted by these events and saw it as only a temporary inconvenience. Smugglers' hiding places were so ingenious that the remnants of old tunnels often leading to the local churches are still being discovered today, especially on Middle Street, the centre of Deal's excise-avoiding activities. The Rattling Cat in Walmer, an old coaching inn, is said to get its name from the fact the owner kept many cats with pieces of bone attached to their collars. When strangers appeared in the area, the cats would run home, and the rattling of their collars would alert everyone that there might be Excise men in the area.

The Time Ball Tower was built in 1820 originally as a semaphore post to pass messages along the coast. It is now a museum relating to communication on Prince of Wales Street. Thirty years later, the ball mechanism was installed on the top of the building and connected by telegraph to The Royal Observatory in Greenwich. At precisely 1 o'clock every day, the giant ball was dropped from a pole atop the tower to enable ships at anchor on the Downs to accurately synchronise their chronometers.
Deal barracks were built in the late 18th century and developed into a Royal Marines' depot, barracks, and hospital. The East Barracks later served as home to the Royal Marine School of Music. With the advent of steam ships in the 19th-century, ships no longer needed to take shelter at Deal and the importance of the town as a port began to wane. During the Victorian era, it then reemerged as a tourist resort. The first wooden pier was constructed in 1857 and later replaced by an iron pier in 1864. The current pier was opened in 1957 and the new end with the pier restaurant in 2008. Looking back from the end gives a snapshot of Deal's varied past, the beautiful old houses along the seafront forming a colourful backdrop to the vibrant bustle of the old town.

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