TrailTale

Winchester Heritage Trail of Castles and Rivers City Walk

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