Winchester is a city like no other, boasting two castles and a rich history that traces back to Alfred the Great, who made it his capital. This legacy has left Winchester with an extraordinary blend of historical and religious landmarks, from its magnificent Cathedral to the remnants of its medieval past.
As you stroll along the picturesque River Itchen, you might feel as though you’ve stepped into a quaint Swiss town, with charming views and a serene atmosphere. Winchester is a place that enchants every visitor, and if you’re lucky enough to hear the grand organ or a choir rehearsing in the Cathedral, your experience will be truly unforgettable.
With so much to see, TrailTale has carefully curated this walking tour to guide you through the city’s most fascinating highlights. Join us as we uncover the very best of Winchester’s history, beauty, and charm!

This walk covers a route, which is about 2 miles long (3.2 kms), and should take you about 2 hours of mostly easy walk to complete. There is a portion of a steep ascent just before you walk up to the Peninsula Barracks.
I suggest parking your car in Chesil St Multi Storey Car Park, Barfield Cl, Winchester SO23 0HU. Cost is £2.10 for 3 hours.
The following Points of Interest are covered:
Winchester City Mill
Winchester City Bridge
Roman Winchester
River Itchen
Wolvesey Castle
Winchester College
Jane Austen
King’s Gate
Deanery & Close
Pilgrims’ School
Winchester Cathedral
Serle’s House
Peninsula Barracks
John Colborne
Winchester Castle
The Great Hall
The Westgate
Winchester
The Butter Cross
Winchester High Street
The Coloured Bollards
Alice Lisle
Provident Dispensary
Morley College
St Maurice Covert
Winchester Guildhall
Abbey House
Alfred the Great
St John’s Hospital – Almshouses