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Chester draws

Sunday People

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January 18, 2026

After exploring its ancient walls, charming cafes and cobbled streets, JULIE DELAHAYE sees why Chester deserves its title of world s prettiest city

- Edited by JULIE DELAHAYE

A rainy, windy morning isn’t exactly ideal when you're visiting a new city that’s renowned for being picturesque. Given the dreary skies and bone-chilling gusts, I was starting the day in a bad mood when heading to Chester, so I fully expected to arrive and - with classic British optimism - be disappointed.

However, within half an hour of wandering around, it was evident as to why it’s been given the accolade of “world’s prettiest city”.

It’s as if Chester has been frozen in time. To enter the centre you have to walk under the impressively preserved Roman walls.

At nearly two miles long, they make up the oldest, longest and most complete city wall circuit in Britain, with parts dating back 2,000 years.

You can climb some steps and walk along the top of the fortifications to enjoy unrivalled views of the city and surrounding Cheshire landscape, on a loop that takes about 45 minutes.

Back on the ground, stepping through the archways leaves you feeling like you've arrived on a film set.

There's something particularly charming about the crooked buildings that make up the high street, packed with independent shops, bookstores and cosy cafes, all of which sit alongside some of the larger chains.

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