‘What to do in Winchester’ into Google brings you back a bunch of generic things. We are not saying they aren’t good things to do. You know who doesn’t love taking a look at some animals at Marwell Zoo?! You just can’t go to Marwell Zoo every single time right… 

We want to write this blog to help you plan a good day, afternoon or evening out in Winchester. Because there are a whole bunch of things to do that are a bit different, a bit quirky or just really good things to do there. 

We are writing this particular piece for people that live in and around Winchester, although we accept that people that are day trippers or passing through are equally interested in what to do here. We would imagine the fact that Winchester is a regular feature in the top 10 places to live in the UK has a large bearing on this! 

Enough blabber… here are some things to do that we think are really worth it. 


This is not necessarily the best thing to do in Winchester it just so happens it is at the front of mind!

St Catherine’s Hill is really easy to access on a walk along the River Itchen and through some of the magnificent sports fields that belong to Winchester College (or Win Coll to those in the know.) 

Kick off with lunch or a drink at The Black Boy on the river and then head along the river to College Walk through the playing fields and towards St Catherine’s Hill. It is a bit of a climb to the top but it makes for beautiful views of the town and St Cross. 


 This is the walk we would do on the way from the Black Boy to St Catherine's Hill
This is the walk we would do on the way from the Black Boy to St Catherine’s Hill


Talking of St Cross you can continue the walk back down the hill and along the river to the Hospital of St Cross. It was in Wolf Hall, Google reliably says, and is an interesting almshouse to have a look around. That second part is a fact, not just according to the search engine. If you are lucky there might even be a bit of cricket on next door.

Luckily there is a different way back to Winchester. Buses or a different path to walk back on! 

Winchester Pub Crawl

Winchester is blessed with some excellent pubs. We have already mentioned The Black Boy which is in a nice setting at the bottom of the town. Another real cracker with a lot of character is The Wykeham Arms – you will see what we mean as soon as you step into the place. 

The best way of getting from one to the other is via the River Itchen where you will pass the Wolvesey Castle, Winchester College, the very pretty P&G Wells bookshop and a homage to Jane Austen. 

Along the river path there is also the Bishop on the Bridge which is a good place for some views. 

Most of this walk is actually on one of the walks we have created on our app, where you can solve 10 questions based on what you see in 60 minutes. You can take a look at the walks here. And download the app here. 

on to the famous sights then

So the main sights are still worth popping into. 

Winchester Cathedral is a stunning piece of architecture. Wikipedia tells us that it is one of the largest cathedrals in Europe, with the longest nave and greatest overall length of any Gothic cathedral in Europe. So that is something. 

The Great Hall contains perhaps the greatest symbol of medieval mythology, King Arthur’s Round Table, and is now all that remains of Winchester Castle. There is also the underground passages nearby and an interesting mural near the steps to the Great Hall and the Law Courts. 


 The Mural Round Table near The Great Hall
The Mural Round Table near The Great Hall


The Viewpoint at the bottom of town is quite a climb, but once you are there, you have a stunning view across the city. The way down is a lot, lot easier. We do have a Tramble walk that goes there too >> You can take a look at the walks here. And download the app here. 

Winchester College Tours take you round the school that has been chugging along since 1382. The website linked before is the best place to find out more about the tours but you will guarantee some excellent pictures of the college and the architecture. 

something different to do in winchester

We are obviously big fans of codebreaking challenges, riddles and the like – that was one of the reasons we created the Tramble App. 

One thing we love is the Escape Room via Clue Capers in Winchester. Solve their hour long puzzles in a group to see if you can escape the room >> More here.

Where should you eat in Winchester

Forte Kitchen >> Simple but tasty, rustic British food run by Olly and Naomi. An excellent choice when you are in the city. 

Chesil Rectory >> The Chesil Rectory is a big winner for aesthetics. The building itself is stunning. The food is equally as good. Definitely check it out for a stand out meal in Winchester. 


 The Chesil Rectory
The Chesil Rectory


Tom’s Deli >> Run by an Italian family, we love Tom’s Deli. It is friendly, relaxed and a real asset to the community.

Josie’s Cafe >> The Josie’s brand is growing with a few local coffee shops in the Hampshire area now. They are genuine, welcoming and serve brilliant coffee. 


So that brings us to an end of the things we love in Winchester, and the things we recommend doing while you are there. 

Whether you have half a day, a weekend or an evening this blog should stand you in good stead so you make the most it. 

Have we missed anything? 

Let us know in the comments! 

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