Cheesefoot Head – The City Bridge loop from Stonywalls Plantation

Hiking trails & Routes

Cheesefoot Head – The City Bridge loop from Stonywalls Plantation

Hard

4.8

(5)

hikers

Cheesefoot Head – The City Bridge loop from Stonywalls Plantation

07:08

26.4km

340m

Hiking

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Last updated: August 23, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

South Downs National Park

Waypoints

Start point

Get Directions

2.79 km

Lane End Copse

Forest

5.80 km

Bench With a View of South Downs

Highlight • Viewpoint

9.10 km

Cheesefoot Head

Highlight • Natural Monument

The large natural amphitheatre of Cheesefoot Head marks the first great view you experience along the South Downs Way, with views stretching to the Solent and the Isle of Wight. There are three bowl barrows (a type of burial mound or tumulus) at the beauty spot.

Tip by

10.2 km

Telegraph Hill

Highlight • Natural

Beautiful walking trails of the South Downs Way. For some long distance walkers, this is where the trail has left Winchester and starts to become more rural. For others, Winchester is close and the end is near!

Tip by

15.1 km

The City Bridge

Highlight • Bridge

a key landmark that crosses the River Itchen right next to the famous Winchester City Mill on the eastern edge of the city centre.

Tip by

15.2 km

The Weirs, Winchester

Highlight • Viewpoint

The Weirs is a stunning walkway located at the bottom of the high street and behind Wolvesey Palace and the cathedral. Swans, ducks and moorhens are often seen paddling about and the stretch is amazingly serene, considering it's just a stone's throw from the main thoroughfare.

The Weirs is a good starting point for walks along the Itchen, an important chalk stream and abundant in fish and wildlife. The Itchen Way, a long-distance footpath, also runs along this lane.

Tip by

15.7 km

Winchester College

Highlight • Historical Site

Founded in 1382

Tip by

16.0 km

Wolvesey Castle (Old Bishop's Palace)

Highlight • Historical Site

The medieval bishops of Winchester were powerful men and Wolvesey Castle was one of the most important buildings in England at the time. Whilst the castle might be in ruins these days, it still has a sense of the grandiose about it. Also known as ‘Old Bishops Castle’, the site is managed by English Heritage and is free to enter between 10am-5pm, daily, from April until October. For more information, visit: english-heritage.org.uk/visit/places/wolvesey-castle-old-bishops-palace.

Tip by

16.5 km