Oldest City in England: Who Really Holds the Title?

When people ask about the oldest city in England, a settlement with continuous urban status since ancient times. Also known as Britain's first city, it’s not just about age—it’s about survival, function, and how we define "city" in the first place. Many assume it’s London, but that’s a common mistake. London grew big and loud, but it wasn’t the first to rise. The real contenders stretch back over 2,000 years, to when Romans first dug trenches and built walls across this island.

The top three names you’ll hear are Colchester, the first Roman capital of Britain, founded in AD 43, Winchester, the capital of Anglo-Saxon England and home to a continuous cathedral since 642, and York, a major Roman military hub called Eboracum that later became a Viking stronghold. Colchester has the earliest claim as a Roman town, but it lost its city status for centuries after the Romans left. Winchester held power through the Saxon kings and kept its identity. York never stopped being important—even under Viking rule, it stayed a center of trade and governance. London? It was rebuilt after the Romans, then burned by the Saxons, then ruled by the Danes. It didn’t become England’s undisputed capital until the 12th century.

The confusion comes down to definitions. Is a city defined by population? By walls? By a cathedral? By royal charter? The UK doesn’t have one official rule. Colchester was granted city status in 1974 based on its Roman past. Winchester’s status came from its royal and religious role. York’s was tied to its medieval importance as a northern power center. Even today, the oldest city in England depends on who you ask. Some go by continuous settlement. Others look at when a place got its official charter. Some care about archaeological layers beneath the streets. The truth? All three—Colchester, Winchester, York—have deep, unbroken roots. London might be the biggest, but it’s not the oldest.

What you’ll find in the posts below are deep dives into these claims, the records that back them up, and the forgotten stories behind each place. You’ll see how the London Gazette, the UK’s oldest continuously published newspaper since 1665, once reported on these ancient towns. You’ll learn why the Berrow's Worcester Journal, the oldest weekly newspaper still running, mentions Roman ruins in its archives. And you’ll understand why no single answer satisfies every historian—because history isn’t a scoreboard. It’s a conversation across centuries.