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The Medway area has a long and varied history dominated originally by the city of Rochester and later by the naval and military establishments principally in Chatham and Gillingham.

Rochester was established on an Iron Age site by the Romans,who called it Durobrivae (meaning "stronghold by the bridge"), to control the point where Watling Street (now the A2) crossed the River Medway. Rochester later became a walled town and, under later Saxon influence, a mint was established here. The first cathedral was built by Bishop Justus in 604 and rebuilt under the Normans by Bishop Gundulf, who also built the castle that stands opposite the cathedral. Rochester was also an important point for people travelling the Pilgrims' Way, which stretches from Winchester to the shrine of Thomas Becket at Canterbury. The Pilgrims' Way crossed the Medway near Cuxton.

In Rochester, parts of the Roman city wall are still in evidence, and the city has many fine buildings, such as the Guildhall (today a museum), which was built in 1687 and is among the finest 17th-century civic buildings in Kent; the Corn Exchange, built in 1698, originally the Butcher's Market; the small Tudor house of Watts Charity endowed by Sir Richard Watts to house "six poor travelers" for one night each; Satis House and Old Hall, both visited by Queen Elizabeth I, built in 1573.

The Royal Navy opened a anchorage dockyard in Gillingham (Jillingham Water) during the reign of Henry VIII, in 1567 the Royal Naval Dockyard was established in Medway. Although it is called Chatham dockyard, two-thirds of the dockyard lie within Gillingham. The dockyard was closed in 1984, with the loss of eight thousand jobs at the dockyard itself and many more in local supply industries, contributing to a mid-1980s Medway unemployment rate of sixteen percent. It was protected by a series of forts including Fort Amherst and the Lines, Fort Pitt and Fort Borstal. The majority of surviving buildings in the Historic Dockyard are Georgian. It was here that HMS Victory, Admiral Lord Nelson's flagship at Trafalgar, was built and launched in 1765. Sir Francis Drake learned his seamanship on the Medway; Sir John Hawkins founded a hospital in Chatham for seamen, and Nelson began his Navy service at Chatham at the age of 12. Other notable sea-faring and naval figures, such as William Adams, were raised on the Medway but apprenticed elsewhere. The river was further protected by such fortifications as Upnor Castle which, in 1667 in varying accounts says it was partly successful in thwarting the Dutch raid on the dockyard, or the commanding officer fled without firing on the Dutch. 

Another warship built at Chatham that still exists is HMS Unicorn (a 46-gun "Leda" class frigate) laid down in February 1822, and launched 30 March 1824. She never saw active service and has been restored and is (as of 2005) preserved afloat in Dundee, Scotland. There have also been other naval disasters in Medway other than the Raid on the Medway.

On 25 November 1914 the battleship HMS Bulwark was moored at buoy number 17 at Kethole Reach on the River Medway. She was taking on coal from the airship base at Kingsnorth, on the Isle of Grain when an internal explosion (most likely the result of cordite charges stored alongside a boiler room bulkhead and failure to follow guidelines on the storage of shells) ripped the ship apart. In all, the explosion killed 745 men and 51 officers. Five of the 14 men who survived died later of their wounds, and almost all of the others were seriously wounded. There are mass and individual graves in Woodlands Cemetery in Gillingham for the Bulwark's dead, who were mostly drawn from the Portsmouth area. The explosion could be heard from up to 20 mi (30 km) at Southend and Whitstable. In terms of loss of life it remains the second worst explosion in British history.

Less than six months later there was a second explosion. This time it was the Princess Irene. She was a 1,500-passenger liner built at Dumbarton in 1914 for Canadian Pacific. Before she could leave Britain she was commandeered for war service and became HMS Princess Irene, and was used as a minelayer. After several trips she was back in the Medway for a refit when on the morning of 27 May 1915 a huge internal explosion tore through the vessel, shaking the ground for miles around and showering the surrounding villages with remains of bodies and debris. 278 died, including 78 workers from nearby towns and villages. In one Sheerness street there were ten who died. A Court of Inquiry was held into the loss and evidence was given that priming of the mines was being carried out hurriedly and by untrained personnel. A faulty primer was blamed for the explosion.

The British Army also established barracks here; and the Royal Engineers headquarters is in Gillingham. The Royal Marines also have a long association with Chatham. The Chatham Division was based in Chatham until the closure of the Chatham Dockyard. A museum dedicated to the Royal Marines can be found close to the dockyard at the Royal Engineers Museum in Brompton. Founded in 1812, it moved to its current site in 1987. It was classed as Grade II listed on 5 December 1996.

Charles Dickens lived in the town as a boy, both in 'The Brook, Chatham' and in Ordnance Terrace before Chatham railway station was built just opposite. He subsequently described it as the happiest period of his childhood, and eventually returned to the area in adulthood when he bought a house in nearby Gad's Hill. Medway features in his novels. He then moved to Rochester, a nearby town, also part of the Medway Towns. Others who were born or who lived or live in Chatham:

Percy Whitlock, organist and post-romantic composer
Richard Dadd, Victorian-era painter and patricide
William Coles Finch, author and historian, lived at Luton, Chatham.
Elizabeth Benger, biographer, novelist and poet, was brought up here between 1782 and 1797.[37]
Billy Childish, artist, poet, and musician
Tracey Emin, artist and member of the Young British Artists
Zandra Rhodes, CBE, RDI, designer
Bill Lewis, poet, painter, storyteller and mythographer
William Ridsdel, Salvation Army Commissioner, lived in the town from 1877 to 1878.
William Cuffay, Chartist leader and tailor, born in Chatham in 1788
Gemma Lavender, astronomer, journalist and author, born in Chatham in 1986

Lower Upnor faces Upnor Reach. It was a single row of houses, separated from the river by the roadway and the hard. Located here is the Arethusa training centre, run by the Shaftesbury Homes. In 1849, HMS Arethusa was the name of the training ship moored near the shore. The society had moored a training ship here for over 105 years. The first was the Chichester, but after then all the ships were called Arethusa. The last but one Arethusa was the Peking, one of the R.F Laeisz's Flying P-Liner four-masted barques, built in 1911, and acquired after 1918 as war reparations. She was sold in 1975 to the South Street Seaport Museum in New York. The last Arethusa, a 23-metre two-masted ketch, was sold in 2000 and now sails with the Cirdan Sailing Trust under the name Faramir.

Lower Upnor is also the home of two yacht/sailing clubs. Medway Yacht Club, which was founded in 1880, purchased land in Lower Upnor in 1948, now comprising approximately 14 acres (57,000 m2). Upnor Sailing Club was formed in the 1962 and moved into its present Club House (formed from renovating three existing traditional riverfront cottages) in the 1980s. Upper Upnor comprises a village cobbled high street leading down to Upnor Castle. It has many houses displaying Kentish weatherboarding, some are Grade II listed. It also has some terraced streets formerly used by the MOD and also Castle Street. It is on Chatham Reach directly opposite St Mary's Creek.

Upnor Castle was built as an artillery fort between 1559 and 1567 in order to protect Chatham Dockyard and the associated naval anchorage. It was called into action in June 1667 when the Dutch Navy conducted a raid on the ships moored in the river; the castle proved ineffective in repelling the attack and it was decommissioned soon afterwards. Though the castle was only operational as a fort for about 100 years, it was retained as a magazine and ammunition store until the end of the First World War; continuing in military use through World War II, it was opened to the public as a museum in 1945. Upnor Castle served as a gunpowder magazine for the Board of Ordnance from 1668, providing powder for the defences of Chatham Dockyard and for the fleet based in the Nore. In 1810 a new magazine with space for 10,000 barrels of gunpowder was built downriver from the castle (which had long needed to expand its capacity) along with a 'shifting house' for inspecting powder that had arrived by sea (though demolished, its surrounding earth traverse is still in evidence, midway between the magazine and the castle).

In 1856 a second magazine was constructed alongside the first, to the same design but with more than double the capacity; (this still stands on the river bank, the earlier magazine having been demolished in 1964). At the same time, buildings were constructed (alongside the shifting house) for storing and maintaining artillery shells; but these soon proved too small, so the site began to be extended to the north, where additional shell stores were built from the 1860s onwards. A little further to the north, a group of large houses were bought to serve as offices for the depot. There was not enough space, though, for further bulk storage of gunpowder, so in 1875 a separate set of five magazines were built, inland at Chattenden, and linked to Upnor by a narrow-gauge railway (see below); the Upnor magazines were then converted into filled shell stores.

In 1891 Britain's Ordnance Yards were split between the Admiralty and the War Department, Upnor going to the former, Chattenden to the latter. The Admiralty therefore embarked on building a new inland depot, next to Chattenden, at Lodge Hill; opening in 1898, it dealt principally with cordite. At Upnor itself further Shell Stores was built in the 1880s, supplemented by new buildings for storing wet and dry guncotton (used in torpedoes and mines) in 1895. The site was extended further to the north in the early 1900s to allow construction of a much larger store for filled shells and another for mines. At the same time a complex of buildings for filling shells with powder (and later also with trotyl and amatol) were added behind the original 'A' and 'B' magazines.

The three sites, Upnor, Lodge Hill and Chattenden, were active as Royal Naval Armaments Depots until the mid-1960s. Thereafter they remained in military hands as part of the Royal School of Military Engineering until the mid-2010s.