On the off chance that you are looking for a challenge, you came to the right place. This 42 km (26 miles) hike marathon is perfect for someone with hiking experience and a good fitness level because hiking in the South Downs is no walk in the park. Let me take you around this tough and long-distance Winchester Circular Walk. Are you ready for the challenge?
Disclaimer: Some hiking groups may offer the same or similar long-distance walks in the Winchester area. Please check here for more details.
Logistic for the Winchester Circular Walk
- Distance: 26.59 miles (42.8 km)
- Total Ascent: 2495 feet (760.47 m)
- Highest Point: 568 ft (173 m)
- Lowest Point: 108 ft (33m)
- Difficulty: Challenging
- Duration: 10 hours and 50 minutes at an average speed of 4.11km/hour
- How to get there:
- Train from Waterloo Station directly to Winchester Station. The journey takes just under an hour.
- It is a circular walk so you can book a day return ticket
- What to pack:
- A lot! Comfortable clothing and footwear. Prefer hiking shoes or boots with ankle support as you will be going up and down hills.
- Water, at least 3 litres recommended, and to keep yourself hydrated add electrolytes.
- Sunscreen and a headcover if you are going on a bright day as a lot of parts of this walk are exposed.
- Rain gear if your a going on a rainy day for the same reason as above
- For food, you need to carry with you snacks that are high in carbs such as dried fruits, bananas and dates. Bring fruit cakes you can eat after you finish as they contain proteins that help with the recovery. Don’t forget a packed lunch and prefer a lunch jammed packed with carbohydrates
- Bring a bottle of full-fat Coca-Cola to drink during the afternoon for a quick energy boost when you start feeling tired.
- Comfortable clothing and footwear. Hiking boots with ankle support are recommended due to the ascent on this walk
- Pair of gaiters if it has been raining before
- Hiking poles are highly recommended
- Additional Information
- There are no public toilets on this walk
Highlights of the Winchester Circular Walk
- Winchester
- Beauworth village
- Kilmeston village
- Upham village
- Owslebury village
- St Catherine’s Hill
- River Itchen
- King Alfred the Great Statue
- Winchester Guildhall
The Winchester Circular Walk
Winchester
We start the walk in the first and former capital city of England: Winchester. Located 60 miles (97 km) from London, Winchester is considered one of the most costly urban areas in the United Kingdom. Its history traces back to the Iron Age. From the seventh century, it became the heart of the royal administration and King Alfred the Great capital city. Among its most famous landmark is the Winchester Cathedral which was built in 642.
As you come out of the train station, take City Road and continue straight onto North Walls until you reach the River Itchen. Then, turn right and follow the path by the river until the end. Cross over the street and go down to continue your way by the river on the other side. Keep strolling alongside the River Itchen where you will see the back of St Peter’s Church where inside you can find the Chesil Theatre.
Cross the bridge and walk up Petersfield Road. At the end of the road, you find a footbridge to go over the M3.
From Winchester to Beauworth
On the other side, you set foot on the fields and walk on the path bordered by long grass. This is where you start climbing the tallest hill of this hike, Telegraph Hill. Once at the top, you enter a forested area and continue until you come out at a crossroad. This is a perfect spot where to stop for a morning snack.
You can admire the beauty of the South Downs, a range of chalk hills stretching across 260 square miles (670km2) from the Itchen Valley in Hampshire to Eastbourne in East Sussex. The site is characterized by its rolling landscape and dry valleys. It is one of the main chalk landscapes in England.
You leave the endless green fields and arrive at the village of Beauworth. Upon entry, you are welcomed by a sign saying: “Chicken Crossing” (try not to laugh when you see it).
The wonderful village of Beauworth with its thatched cottages was made famous on 30th June 1833, when four boys under the age of 10 who were playing marbles in a pasture land discovered a treasure. More than 6500 coins were uncovered and believed to be linked to Wakelin, the first Norman bishop of Winchester.
Beauworth to Street End
You continue walking in the long grass fields until you reach the village of Kilmeston. This small village is the home of two Grade II listed buildings: a manor and a church which was initially erected during the Middle Ages and rebuilt in 1772. The green is the perfect spot for lunch. You can either chose to stay in the sun or find some shade underneath the trees. You will find public toilets in the village hall however, it is not always open.
After lunch, make a turn and start walking in direction of Preshaw Estate. On the way, you meet with lambs rushing to the fence to welcome you. Say your goodbye to the green long grass meadows as you are now entering a section of the walk where you are passing through crop fields.
You then start climbing the second highest hill of this hike, passing through Preshaw Estate. Just before leaving the estate, beware the bulls. Out of nowhere, a herd of bulls came running towards us. They stood in front of our group, obstructing the path. Lucky for us, one of the group members was not as afraid (unlike the rest of us who stood there petrified). He clapped his hands to scare them and they ran away. It’s good to know!
Preshaw Estate to Owslebury
Continue walking alongside the path in direction of Street End. Just before reaching the village, you come face to face with another steep hill, but this time smaller. From the top, you have a stunning view of the valley and the village at the bottom. It is worth the effort! I would suggest that you take your first afternoon break at the top to enjoy the view for a little bit longer.
At Street End, make a turn and start making your way back towards Winchester. This is the last stretch of the hike, but not the easiest! Continue walking up and down the endless green fields until you reach Upham. The hilltop village counts a post office, a primary school, two pubs and a church named Blessed Mary.
From there, take the direction of Owslebury village. On the way, you are passing by meadows where cows are grazing. Just before reaching the village, you can stop for the second afternoon break in a field with intriguing designs in the crops.
Owslebury to Winchester
The village of Owslebury is located on top of a hill. Well known for being the centre of the Swing Riots in November 1830 where agricultural workers requested more money or they would take steps to destroy agricultural machinery if their demands were not met. If you go to Owslebury on the last weekend of May, you can enjoy the Scarecrow Trail, a competition of the best scarecrow organised in the village.
For this last part of the hike, you will be walking on chalk paths, quite hard to the feet, especially after so much distance travelled. This up and down stretch highlight is the sight of the sun going down on the countryside. An opportunity to take incredible pictures. But don’t waste too much time, you need to be back in Winchester before dark!
Just before reaching Winchester is St Catherine’s Hill. You can either get around the hill and take the path at the bottom (which I did) or go up the hill if you still have energy! After St Catherine’s Hill, it is a flat walk alongside the River Itchen all the way to Winchester.
Back to Winchester
Once back in the city, you can take an alternate course to return to the train station. Rather than following the River Itchen as we did when we started, turn onto The Broadway. There you encounter the statue of King Alfred the Great.
A little bit further down is the Winchester Guildhall. The site in which the Guildhall is constructed was originally a nunnery established by Aelswith, the widow of King Alfred the Great. It was demolished in 1538 under the order of Henry VIII. It’s in 1870 that the idea of building a Guildhall on the site came about. The building has since been refurbished many times. It serves as a banquet hall and for council meetings. Since its closure due to the Covid -19 outbreak, the Guildhall has been used for HM Court and Tribunal administration.
You will find plenty of restaurants on the High Street and all the way to the train station where you can have a comfort meal and a drink (or two). When I went for this hike marathon we did not book in advance, so we went to an Italian restaurant chain where they had a table available. Of course, you can be more organised than us and plan ahead for diner. Bon appetit!
The Winchester Circular Walk Map
If you are doing this Winchester circular walk or know about another version of this hike, please let me know in the comments section below, I would love to hear about your experience!
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Finally, if you are looking for additional difficult walks, check this articles
Walking The Thames Path To Windsor
Berkhamsted Circular Walk: Between Hills and Canal
