The Westgate is one of only two medieval city gates to survive in Winchester (the other being Kingsgate), and it has served as a debtor's prison, a house of correction, and — for the past century — a small museum. The gate dates from the 12th century in its lower portions, with later medieval additions above. The upper room, used as a prison until the 19th century, still has prisoners' graffiti scratched into the walls.
The museum inside is modest but worthwhile: weights and measures, a collection of 16th-century painted weights, and displays on the city's medieval history. The roof offers a useful view along the High Street. The gate sits at the top of the High Street, making it a natural endpoint to a walk up from the Butter Cross, and admission is inexpensive.