St Catherine's Hill – The City Bridge loop from Winchester

Hiking trails & Routes

St Catherine's Hill – The City Bridge loop from Winchester

Moderate

5.0

(4)

hikers

St Catherine's Hill – The City Bridge loop from Winchester

04:58

18.2km

270m

Hiking

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: October 8, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

South Downs National Park

Waypoints

Start point

Train Station

Get Directions

623 m

Westgate, Winchester

Highlight • Historical Site

This is the Westgate and it contains a tiny museum which you should visit when open. You can also step outside at the top to enjoy a view down the High Street.

Tip by

3.18 km

View from St Catherine's Hillfort

Highlight • Viewpoint

Chalk on slope is very slippery after rain. Cafe on cyclepath at the bottom is a lovely pitstop.

Tip by

3.28 km

St Catherine's Hill

Highlight • Historical Site

This wonderful lookout point is the site of an Iron Age hillfort as well as a thriving nature reserve. The summit stands 230 feet (70 m) above the River Itchen …

Tip by

11.0 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. …

Tip by

12.1 km

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

13.2 km

Chilcomb Wood

Forest

16.7 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

16.8 km

Statue of King Alfred the Great, Winchester

Highlight • Historical Site

Winchester’s statue of Alfred the Great is one of the city’s most iconic sights. He stands at the bottom of The Broadway next to the River Itchen and the Guildhall, …

Tip by

17.0 km

Winchester High Street

Highlight (Segment) • Settlement

Yes it has a few banks, clothes outlets, and plenty of coffee shops, but nevermind all that. It has so much history on this street. Curfew bells, oldest pub in …

Tip by

18.2 km

End point

Train Station

Way Types & Surfaces

Way Types