A city high street and roads were closed after sudden rainfall caused flash flooding.
Hampshire County Council urged people to avoid parts of Winchester after the flooding at about 19:45 BST.
Easton Lane was closed for almost two hours, according to the authority, and South Western Railway said services between Eastleigh and Winchester had been affected.
Eyewitness Jez Hollinshead said the flooding looked “biblical”.
Mr Hollinshead said he left the Westgate Pub at 17:30 and it had been raining “torrentially” for an hour.
He added: “I thought I spied a break. Turns out I hadn’t. The rain just got heavier and heavier.
“In the end, many of us just gave up to our fate and waded through. At the bottom of town it was a lake. The rain just kept coming and we were all saying to each other how we’d never seen anything like it.”
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