A walk on the South Downs Way from Winchester

by Jan

You will be spoilt for choice if you are looking for places to walk in Winchester.  However, we we were keen to walk on the famous South Downs Way, so chose this long-distance hike, which has its roots in Winchester.  The South Downs Way is one of 16 national trails in England and Wales and runs for 100 miles (162 km) across the South of England.

Walking the South Downs Way

The South Downs Way sign post

The historic city of Winchester, in Hampshire is the official gateway to the South Downs Way.  This national trail crosses over unspoilt English countryside through the picturesque fields and villages on the South Downs National Park.  Eventually, the South Downs Way finishes in the seaside town of Eastbourne, in East Sussex.

You can complete the South Downs Way in about 6-9 days as a multi-day hike, though I have heard of people doing it in 4!  Alternatively, like us, you can choose to walk one section at a time.

As well as walkers and joggers, the South Downs Way is a popular trail for cyclists and horse-riders.

Starting the South Downs Way at Winchester

We started at the National Trust’s Winchester City Mill, which is now the official gateway to the trail. From here the path follows the River Itchen.  This is a short, but scenic stretch beside the water and eases you gently into the walk.  There’s lots of wildlife, struggling against the flow of the water and we saw some extremely cute ducklings and swans.

At the bridge you take a sharp left over the bridge and go straight to the start of the trail.

At least this is what we should have done.  What we did, was follow a parallel path, miss the bridge, and make a minor detour by the ruins of Wolvesey Castle.  However, we soon realised our error and were soon back on the correct trail.

Winchester Mill at the start of the South Downs Way

Only to miss the next turning a few minutes later.  We did wonder why this famous national trail would start off heading through a residential housing estate.  However, spirits were still high and soon we were back on the correct path again.

Quite honestly, the South Downs Trail is waymarked, and it should be impossible to get lost.  So, don’t let our lack of direction put you off.  Thousands of people have been doing it since medieval times and getting it right!


Boys talking to sheep at Chilcomb on the South Downs Way

Most of the first section is through cultivated fields, mostly wheat and corn.  About 3 miles out from Winchester, we came to our first village, Chilcomb.

Chilcomb is a small, pretty village with an old church and some chocolate box cottages.  There were also sheep, so we stopped to have a chat with the lambs.

Spectacular Views

It’s easy to see why the South Downs Way is one of the most popular trails in the UK.  The views are stunning.  You travel through miles and miles of open land and can see for miles around.   We were lucky enough to have picked a sunny day, so it all looked even better.

It’s fairly hilly, with an ascent and descent of 4150 metres, but considered a fairly reasonable trail for walkers of all abilities.  It is certainly less challenging than some of the other long-distance walks in the UK.

Blue sky filled with fluffy white clouds, looking over fields to woods on the South Downs Way

Cheesefoot Head

Information board at Cheesefoot Head gateway to the South Downs Way Trail

Eventually the trail crosses the A272 to arrive at Cheesefoot Head.  Here, you will find a large natural amphitheatre, where General Eisenhower addressed the troops before D-Day in 1944.

This ampitheatre, also known as Matterley Bowl, shaped by melt water in the last Ice Age.  There is a small off-road car park, so would make a good alternative if you didn’t fancy parking in Winchester.

The stretch of walk from Cheesefoot Head follows a woodland path, which provided good shade and a quick tree-climbing stop.  Eventually the path comes out into more fields and we surprisingly found ourselves at the Juniper Leisure Tank Driving Centre.  We’d been here for a tank-driving experience a couple of years ago.

We stopped here for lunch, though it probably wasn’t the most scenic part we’d seen so far.  However, it was here that Thomas spotted a cool bees’ nest, so this lifted our spirits.


After lunch, we turned round and headed back to Winchester. It was easier on the way home and more downhill. Just before entering the city, we stopped at the Black Boy pub for a socially distanced drink in the garden. What a find! This is a quirky pub, with lots of unique collections inside. The boys were a little perturbed by the taxidermy collection, though I thought the baboon looked rather fetching.

You can’t visit Winchester without a visit to the beautiful Gothic cathedral.  It’s one of the largest in Europe and certainly is an impressive sight.

Winchester is a small city but is rich in history and very charming.  The Guildhall is an elaborate Victorian building and there are many other historic buildings and artefacts around the city.

looking up at Winchester Cathedral stain glass windows


South Downs Way Parking

We parked at the long stay car park in Chesil Street, as we wanted to look at the city afterwards.  I would avoid the short stay car parks, as it is very expensive for a long visit.

If you want to miss out the first part of the walk, you could park at Cheesefoot Head.

Eating & Drinking

As you leave the city, you may pass a cluster of pubs, called The Black Rat, The Black Boy and the Black Hole, near Wharf Hill.  However, after this we didn’t see anywhere to buy refreshments, so take lots of water and food.

Obviously, there are plenty of eateries in Winchester, if you are returning, or alternative pubs if you continue further.

For details of more family friendly walks, have a look at:

Walks & Hikes in the UK

Thanks for reading

Thanks for reading our post about our walk on the South Downs Way.  Have you tried it yet?  Please feel free to comment below.

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Avatar for Jan
Ross 22nd July 2020 - 11:44 am

We’ve not tried it Jan but the South Downs really is on our ‘Places’ list. Hadn’t thought about Winchester but we love a good Cathedral so we’ve added it. Thank you and for all the information, it really is very useful. Your photos and descriptions have made it very appealing. Great post! Looks like you had a wonderful, if not tiring, day!

Avatar for Jan
Cindi | aneasyjourney 20th July 2020 - 8:56 pm

So interesting! Our family also really likes to hike & we have not been in this part of England, so looks like a great option. Like your stop at the pub – definitely have to incorporate this is our hike! Can’t wait to read more. 🙂

Avatar for Jan
John 19th July 2020 - 2:07 pm

A good pub is always a find at the end of a hike. Usually cause I’m starving. Give me carbs. This trail just sounds pleasant. I think I’d love it.

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Laureen Dixon 17th July 2020 - 11:27 am

Your family have done a lot of travelling and must be keen walkers, What a wonderful way to educate and bring up boys. They are very lucky!

Keen reader of your site.


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The Wanderer Pharaoh 14th July 2020 - 7:14 pm

Seems like a wonderful experience! long-distance hikes are the best. And Winchester and the landscapes along the way look amazing. Thank for sharing

Avatar for Jan
Vito 14th July 2020 - 6:29 pm

Wow 100 miles! We could definitely get lost in Southern England for a few weeks. Great post!

Avatar for Jan
Jan 14th July 2020 - 7:21 pm

Yes, that’s a very long walk. Not sure we are ready to do it all just yet!


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