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St Catherine's Hill – Cheesefoot Head loop from Winchester

Routes

Hiking trails & Routes

St Catherine's Hill – Cheesefoot Head loop from Winchester

Moderate

5.0

(4)

hikers

St Catherine's Hill – Cheesefoot Head loop from Winchester

04:59

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: April 5, 2026

Tips

Your route passes through protected areas

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

2.76 km

The River Itchen at Fallodon Nature Reserve

Highlight • Trail

Beautiful path along the river, whether you hike or paddle - it is simply wonderful to be able to enjoy pure nature here

Translated by Google •

Tip by

3.23 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

3.32 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

12.2 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

16.8 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

16.9 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

18.2 km

End point

Train Station

Way Types & Surfaces

Way Types

6.82 km

5.78 km

2.72 km

1.72 km

1.17 km

Surfaces

8.07 km

3.38 km

2.76 km

2.72 km

1.02 km

259 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (160 m)

Lowest point (30 m)

Weather

Monday 18 May

16°C

11°C

53 %

Additional weather tips

Max wind speed: 28.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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St Catherine's Hill – Cheesefoot Head loop from Winchester

Westgate, Winchester

The River Itchen at Fallodon Nature Reserve

View from St Catherine's Hillfort

St Catherine's Hill

Cheesefoot Head

Telegraph Hill

The City Bridge

Statue of King Alfred the Great, Winchester

Nearby routes

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