Winchester is a city in the county of Hampshire, on the edge of England’s South Downs National Park, with the river Itchen flowing through the city mill. It’s a city full of history, with Winchester college, one of Europe’s oldest cathedrals, a bustling high street and a good variety of shops and independent coffee shops. The balance of small city and countryside feel, for me makes Winchester one of my favourite cities, and there is plenty to do and explore for all ages – well worth a visit.
The past still echoes strongly around the flint-flecked walls of this ancient cathedral city. It was the capital of Saxon Kings and a power base of bishops, and its statues and sights evoke two of England’s mightiest myth makers: Alfred the Great and King Arthur. Winchester’s architecture can be clearly seen especially in the college buildings, and the narrow back streets which take you to the centre; the cathedral and the cathedral close, a popular place to sit in the summer.
So, here are my top recommendations for exploring Winchester:
Copper Joes & Military museums
- A hearty café connected with the military museums. Enjoy a large variety of great sandwiches, hot chocolate and ice cream on a hot day. The Rifles, Green Jacket and Horsepower museum are also worth a visit, with an impressive diorama of the Battle of Waterloo
The Stables
- A small chain of restaurants specialising in pizza and cider, a relaxed chilled out vibe with funky interior and good food, good anytime of the day.
Walk up St. Catherine’s Hill
- A walk up St. Catherine’s Hill either up the 333 steps or the shorter, steeper side on the other side of the hill. There is a great panoramic view of the city from the top, and if you’re feeling active, it’s a great hill run and is popular with runners.
Flat Whites
- A small independent coffee shop and trailer which does the BEST coffee and latte art, if you’re into your coffee then this place is for you. Plus, the staff are super lovely.
Visit the cathedral
- The cathedral was built in 1079 and was related to William the Conqueror, the impressive crypts and beautiful stained-glass windows are worth a look. If you have time and aren’t afraid of heights and small space, a tower tour is well worth it. The unique viewing of the bell chamber and view of the city from the top of the cathedral is pretty special. The cathedral also runs twilight tours around Christmas time, the city all lit up looks magical.
- Just behind the Cathedral at Christmas time is a great Christmas market, full of huts and food stalls. These surround a covered ice rink that stays up until New Year.
The Wykham Arms
- Arguably the best pub in Winchester, with fab food and located on a beautiful old street, with the old bakery and by the back of the colleges; all makes for a lovely walk back home.
Everyman Cinema
- Not just your everyday cinema, expect plush armchairs and sofas to cosy up in while you watch a film with a glass of wine and pizza that can be delivered straight to your seat by friendly staff. Plus if you become a member of this small chain of cinemas, a free Green&Blacks chocolate bar!
Endless Shopping
- Despite the national death of the high street, Winchester still boasts some of the best high street and independent shops. With Joules, Anthropologie, Waterstones, Primark, The White Company and SpaceNK. If you’re looking for something a bit different, have a peek in Sass&Edge, a wonderful boutique clothes shop. Plus, two beautiful jewellery and gift shops down Parchment street.
Rick Stein
- Many of you will have heard of Rick Stein before, but the Winchester branch is lovely, right down at the bottom of the high street, you can walk past the river Itchen and ‘The bishop on the Bridge’ pub on your way back.
College walk, Canon street, St. James Lane
- With no particular aim, these streets are lovely to stroll down and take in the old city walls and architecture. A lovely time to walk is ‘golden hour’, the half an hour ish before sunset, when the sun casts a beautiful hazy golden glow over everything.



