Winchester walking routes
If you’re visiting Winchester for the first time, or simply wish to explore a little more of the city’s historical sites, we’ve put together 3 walking routes to help you take in some of the highlights, including the 2 remaining gates of Winchester, as featured in our first floor fireplace painting.
The Gates of Winchester were part of the city’s defensive wall, and all but 2 were demolished or destroyed in the 18th Century.
The Westgate – located at the top of the High Street and once part of the fortified city walls, some masonry dates back to the Anglo-Saxon period, although the gate was rebuilt in the 12th century and modified further in the 13th and 14th centuries. The portcullis and two inverted-keyhole cunports (for use with hand-held canons) were added in the 14th century. The Westgate was still in use until 1959, when the High Street was routed around it. Today, it is a museum which offer visitors an insight into Tudor and Stuart Winchester.
The Kingsgate – the gate you see today is probably 14th century and stands on or near the site of one of the Roman gates to the city. It was once the entrance to the royal palace. There is a small church above the gate, called St Swithun-upon-Kingsgate was built in the Middle Ages, and it’s unusual that this was within the old city’s defensive walls.
Our suggested walking routes are generally accessible, but please be aware that Keats’ Walk can get muddy during the winter.
If you’d like a printed version of our walking routes, please pick up a leaflet in The Winchester Bakery when you get your next coffee.
Wessex Loop
1 hour / 2.9 miles
1. Leave the Winchester Bakery and head down the High Street, all the way to The Bishop on the Bridge pub, admiring historic buildings and King Alfred’s statue on the way.
2. Just before you cross the bridge, turn right and follow the path along the river.
3. Take the next left, then right towards the entrance of Winchester College, and proceed down Keats’ Walk.
4. When you reach the road, turn right over the bridge, then right again onto Kingsgate Road. Keep going until you reach the Kingsgate.
5. When you’ve finished admiring it, walk underneath and take a right, following the road as it curves around towards the Cathedral.
6. Enter the Cathedral grounds at the back, then take the cut through at the far corner until you are in front of the Cathedral.
7. Turn around and head straight, past the war memorial (away from the Cathedral), then turn left and follow the road towards St Swithun Street.
8. Turn right, then take a diagonal across St Cross Road to turn right again up St James’ Lane.
9. Just before you reach the single lane bridge over the railway line, turn right through the black metal gates and make your way towards Romsey Road.
10. Turn right down the hill on Romsey Road, past the entrance to The Great Hall, then pass under the Westgate and onto the High Street.
11. Head towards the historic Buttercross monument and arrive back at The Winchester Bakery for a well earned cup of tea and a cake!
Kings & cathedral
45 minutes / 2.1 miles
1. Leave the Winchester Bakery and head down the High Street, all the way to The Bishop on the Bridge pub, admiring historic buildings and King Alfred’s statue on the way.
2. Just before you cross the bridge, turn right and follow the path along the river.
3. Take the next left, then right towards the entrance of Winchester College, and proceed down Keats’ Walk.
4. When you reach the road, turn right over the bridge, then right again onto Kingsgate Road. Keep going until you reach the Kingsgate.
5. When you’ve finished admiring it, walk underneath and take a right, following the road as it curves around towards the Cathedral.
6. Enter the Cathedral grounds at the back, then take the cut through at the far corner until you are in front of the Cathedral.
7. Follow the diagonal path under the trees towards The Square, and arrive back at The Winchester Bakery.
Two Gates
25 minutes / 1.1 miles
1. Head into The Square, then follow the diagonal tree-lined path towards Winchester Cathedral.
2. Take the cut-through to the right of the Cathedral, cross the grounds towards the far corner and out onto Dome Alley.
3. Turn left to admire Kingsgate; continue underneath.
4. Turn right at The Wykeham Arms, onto Canon Street.
5. Keep going until you read the main road, then cross over onto St James’ Lane.
6. Just before you reach the single lane bridge over the railway line, turn right through the black metal gates and make your way towards Romsey Road.
7. Turn right down the hill on Romsey Road, past the entrance to The Great Hall, then pass under the Westgate and onto the High Street.
8. Head towards the historic Buttercross monument and arrive back at The Winchester Bakery.