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.
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Walking the South Downs Way
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.
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!
Chilcomb
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.
Cheesefoot Head
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.
Winchester
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.
Practicalities
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:
Pin for later: A walk on the South Downs Way from Winchester
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