START: The Great Hall and Winchester Castle

The original castle site dates back to the Roman times. After William the Conqueror successfully invaded England (in 1066), he built one of the first Norman castles here in 1067. The Great Hall was built later, in 1222, and is the only part of the original castle that is still standing. The castle was a royal residence until the 1500’s when Elizabeth I became Queen.

You can do tours of the Great Hall, and see King Arthur’s round table here, as Winchester is believed to be the site of Camelot. At the back of the Hall is Queen Eleanor’s garden, beautiful in the summer, and a lovely and tranquil spot.

2. The Westgate

One of the two remaining gateways in Winchester, the Westgate used to be a debtors’ prison and is now a museum.

There are often family-friendly activities going on, and it’s a really good place to learn about the history of Winchester.

3. Winchester Cathedral

It goes without saying that Winchester Cathedral is one of Winchester’s top history spots. The original minster, Old Minster, was founded around 645, and the brick paths around it are where the Old Minster stood. The current structure is Norman, dating to the late 1000’s.  It is the burial place of King Alfred the Great, King Cnut, William the Conqueror’s son, and  Jane Austen (to name but a few!).

If you are visiting Winchester at Christmas, the Christmas market stalls are all around the Cathedral, and it is a truly magical time of year here. There’s also ice-skating, and the carols are also lovely to go to. I recommend picking up a mulled wine and having a wander to see all the Christmas lights about the city.

There is an admission fee for visiting the Cathedral, but it is well worth it.

4. Cheyney Court & Priory Gate

One of Winchester’s most iconic spots, picture-perfect Cheyney Court is the perfect summary of Winchester history. It dates to the 16^th century, as a court for the Bishop, covering the Soke of Winchester.

Adjoining it is the 14^th century Pilgrim’s Hall, which, after the 1600’s was used as a stable block. Look back (and up) once you’ve walked under the Priory Gate, as there is a small Porter’s Lodge above, which was the home of the Cathedral’s organist.

5. Kingsgate

The second medieval gate in Winchester, the Kingsgate as it stands today is believed to date as far back as the 12^th century. Above the archway, on the first floor, is St Swithun-upon-Kingsgate church, one of the few gateway churches remaining. The Kingsgate was one of the gates into the medieval city, and the church used by the lay people.

There’s the lovely Kingsgate Bookshop inside the archway, with a selection of books, maps and prints available to purchase. If you’ve watched the recent Les Mis. film, you can see this stretch of Winchester when Hugh Jackman is fleeing from Russell Crowe near the beginning.

6. Jane Austen’s House & Winchester College

Passing through the Kingsgate, you turn left along College Street. On the right hand side, passing P & G Wells (Winchester’s oldest bookshop) on your right, is the yellow house where Jane Austen lived in her final years. It is said that Jane Austen and John Keats were both frequent visitors at P & G Wells.

Just along from Jane Austen’s house is the beautiful Winchester College. This is one of the many buildings of the College, which offers guided tours that cover much of its history and grounds.

7. Wolvesey Castle

Wolvesey Castle is an English Heritage site with free entry. It’s situated behind the Bishop of Winchester’s current residence, and you could completely miss it if you didn’t know it was there. You have to walk down a path along the side of the Bishop’s residence, and then all of a sudden, you’re amongst its magnificent ruins.

This was the palace of the medieval bishops of Winchester and was classed as one of the most important Norman palaces in the UK. It was used until the 1680’s and was sadly left to fall into ruin.

8. St Giles’ Hill

If you’re after a stunning view over central Winchester and it’s water meadows, St Giles’ Hill is where you want to go. Historically, the area around St Giles’ Hill and The Soke was the wealthy area of the city. At the top of the hill is a park where the ladies and gentlemen of Winchester would promenade around St Giles’ Hill. Definitely worth a visit, although the walk up is steep!

9. Chesil Rectory

The Chesil Rectory is another iconic landmark of Winchester. It dates back to between 1425 and 1450, and is the oldest commercial property in the city. During the Reformation, Henry VIII took over the Rectory and gave it to his daughter, Mary. When Mary got married to King Philip of Spain, she gifted it to the city as part payment for her lavish wedding (which was held at Winchester Cathedral).

It was left to deteriorate, to the point when it was nearly demolished, before being rescued and restored in 1892. It is now an award-winning restaurant, and definitely a must-go on your list of places to eat.

10. END: The Guildhall, King Alfred’s Statue & Abbey Gardens

King Alfred is considered the first King of England. Before him, England was split into kingdoms with different rulers, with Winchester as the capital of Wessex (Alfred’s kingdom). King Alfred is credited with successfully integrating the kingdoms to ‘create’ England. He is also credited with achieving peace with the Danes, who the Anglo-Saxons had continuously been at war with. King Alfred is buried at Winchester Cathedral, and his statue at the bottom of Winchester’s high street is both an iconic and symbolic landmark to the city.

Just in front of King Alfred’s statue is the Guildhall, and behind this, Abbey Gardens. St Johns House overlooks this too, as does the Mayor’s house. The Guildhall was built in 1873, and was built upon the site where a nunnery had been situated since before 899AD (built and founded by King Alfred’s wife, Aelswith). The nunnery later become known as St Mary’s Abbey, and its garden are where this route ends.

There are many more historical spots around Winchester, not to mention all the quaint side streets, but this route covers a fair few of them.