Ipswich

Ipswich claims to be England's oldest continuously settled town—a claim that means little without understanding why. The site at the head of the Orwell estuary offered what early traders needed: shelter from North Sea storms and access to inland routes. By the 7th century, Anglo-Saxon merchants had established 'Gippa's wic'—the trading post that became Ipswich.

Cardinal Thomas Wolsey, Henry VIII's most powerful minister, was born here in 1473. The son of a wealthy butcher, Wolsey rose to become Lord Chancellor and Papal Legate—the second most powerful man in England after the king. He founded a college in Ipswich in 1528; it was dissolved when he fell from favor, leaving only Wolsey's Gate as a remnant. Despite his complicated legacy elsewhere, Ipswich considers him the town's favorite son.

The wool trade made medieval Ipswich wealthy. Ships sailed for Flanders loaded with East Anglian cloth; by the 14th century, the town was a kontor for the Hanseatic League, trading with Baltic ports. Shipbuilding followed naturally—John Barnard's yards built vessels for global trade through the 18th century.

The port remains operational, handling cargo that now includes containers and bulk materials. The University of Suffolk, established at the waterfront in 2016, represents the latest phase: education replacing manufacturing as the economic driver. Ipswich Town FC, promoted to the EFL Championship for 2025-26 after a single Premier League season, anchors local identity.

By 2026, Ipswich tests whether an ancient trading town can reinvent itself yet again—this time around technology, education, and creative industries rather than wool and ships.