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Walking the South Downs Way. Day 1.

The South Downs Way

So you’re thinking of walking the South Downs Way? You’ve done your planning, and perhaps a little training and are wondering what to expect and how realistic it all is? Having recently walked the South Downs Way over eight days, it was one of the best things I’ve done for quite some time and I would thoroughly recommend it. It is challenging and rewarding in equal measure and over the next couple of posts, I’ll be sharing what you can expect over the course of this epic journey across the south.


Winchester to Exton

The first day of my walk was a little nerve-wracking. I was walking the first two days on my own and the trip had been planned very last minute. I am notoriously bad with dates and although I had tried to make sure I had organised somewhere to sleep for each night in advance, I was reasonably confident I’d booked at least one for the wrong day (I was right but that comes later).

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© Natural Earth Data © Mapbox © OpenStreetMap. Click on map to go to Strava

Getting out of Winchester 

If you expect the start of the South Downs Way to be well-signed as you enter Winchester, you will be disappointed because it isn’t. But it is right in the centre of the town at the National Trust Winchester City Mill  (What3Words: weaved.infringe.stole). Having been dropped off a short distance away, I sat on the bench at the start for a minute and then set off. It felt like an underwhelming start … where were the party poppers and trumpets to see me on my way? The lady in the National Trust shop warned me that the South Downs Way is not well signed out of Winchester and she wasn’t lying but thankfully I had a brilliant guidebook with a detailed map. I was off!

Winchester City Mills

It takes about 2 km to get out of the city and you reach the first big hill and views at 5 km. I think I was fueled by nervous adrenaline for most of this. 160 km is the furthest I have ever walked by about 110 km. But the noise and hustle and bustle firstly of the city and then of the M3 motorway gradually fade as you start to climb away from the city centre.


Getting into your stride 

I made two important decisions in the first 5 km of this walk. They were both good decisions which I would suggest are essential. The first was that I would stop roughly every 5 km and have a drink, a mouthful of something to eat, and then check in with my family by WhatsApp. I agreed with myself that if I needed to stop more often that was OK too but the 5 km was a rule. And in fact, the day felt much less daunting broken down into 5 km chunks. Although I was sharing my journey on social media, I was also careful not to post where I was on those first two days on my own. The second decision was to make sure I filled up with water at every water station whether I needed it or not. There are plenty of water stations for those walking the South Downs Way but some of them are very far apart and some can be easy to miss.

Start of the South Downs Way

As you head up to cross the A272 at Cheesefoot Head away from Winchester, you catch the first views of the walk and can see the Science Centre. I’d seen this on the way in and so it felt like the first small win of the day to be back here. At this point, I was still excitedly telling everyone I passed that I only had 155 km to go although to be honest, some were more interested than others! But it was beginning to feel real. From Cheesefoot you go through the woods and then drop down until you turn right and follow an undulating path. From here I did not pass anyone for the next 10 km apart from when I passed through a small farm.

South Downs Way

Digging in 

At 10 km there is a conveniently located bench provided by the Friends of the South Downs Way. My shoulders were aching from my backpack and my feet hurt but it was a good, if remote, spot for a late lunch. The South Downs Way doesn’t really feel like the South Downs Way as I know it here but it is a really pleasant section that takes you via the edge of fields until you again cross the A272 and pass through Holden Farm. From there, a woodland path eventually takes you out onto a country lane to a little hamlet called The Milbury’s. There’s a little bit of roadwork here but it’s not unpleasant and once off the road and back on the track, you have views and a gentle winding path until the last ascent of the day at Beacon Hill to Exton.

South Downs Way

My first mistake 

At 15 km I checked the location of my Airbnb for the night in West Meon. When I booked it, it looked really close to the South Downs Way but the reality was that it was over 4 km away from my route. Big mistake. I had started from Winchester late and was now worried I might run out of daylight if I had to add 4 km onto my planned 20 km. I was also worried that I might struggle to find somewhere to eat on a Sunday night. I was right. In the end, I ended up doing about 24 km on that first day, finishing with a hill and I could not have walked another step.

Feeling exhausted and doubtful of my ability to succeed in my 160 km mission, it was an early, dinnerless night. I washed out my shirt in the shower ready to re-wear and was grateful for a bed. Known as I am to be overly dramatic, I then messaged my family “I am broken”. Only 140 km plus the walk back to the South Downs Way to go!

Highlights of this section:

  • Getting started
  • The first great views at 6.5km
  • Recognising where you are for the first time


  • Route distance: 19.5km
  • Elevation 340 m
  • Coffee mobile shop as you cross the A272
  • First water station about 1 km after crossing the A272
  • Bench 10 km
  • Second water station at Holden Farm
  • Café and camping at Holden Farm
  • Village shop, B&B, and pub in Exton (fully booked when I walked)
  • Parking at Cheesefoot Head and Beacon Hill

If you are thinking of walking the South Downs Way, you may be interested in:

An Overview of the South Downs Way

Discover the South Downs  

Walking the South Downs Way. Day 2

Planning your South Downs Way Walk 

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