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48 Hours in WINCHESTER

February 2026

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Practical Caravan

Our regular series highlights top attractions and itineraries to help you make the most of a weekend visit

- Paul Critcher

48 Hours in WINCHESTER

IT’S NO GREAT surprise that this beautiful medieval city in the heart of Hampshire frequently crops up on lists of the best places to live in the UK. Its combination of historic landmarks and association with notable figures such as Alfred the Great and novelist Jane Austen makes it one of the county’s most significant locations. Throw in its proximity to the South Downs National Park, a thriving town centre, with noteworthy buildings such as Winchester Cathedral and The Great Hall, and a reputation for some of the best schools in the country, and you can see why it’s such a desirable city in which to live.

DAY 1

9am Juice at Josie's

Grab a delicious brekkie at this central café-restaurant with speciality coffee, pancakes, smoothies and fresh juices being just a few of the treats on the menu. > josies.uk

10am City walk

Get a feel for Winchester’s historic routes with a wander across town, taking in the Buttercross Monument and the City Mill. The medieval City Cross (or Buttercross) was restored in 1865, yet dates from much earlier. It depicts 12 figures, including the Virgin Mary and several saints, and was once used as a place to sell produce.

It’s a short walk along the high street (less than 10 minutes) to Winchester City Mill, which is one of the oldest watermills in the UK, having been rebuilt in 1744 and partially restored in 2004. On the way, be sure to stop for a photo of the statue of Alfred the Great on The Broadway. Alfred made Winchester the capital of the Kingdom of Wessex and is buried in the nearby Abbey Gardens, the site of Hyde Abbey, which was demolished in 1539. > nationaltrust.org.uk

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