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Hiking trails & Routes

South East England

Telegraph Hill – Cheesefoot Head loop from Winchester

Hiking trails & Routes

South East England

Telegraph Hill – Cheesefoot Head loop from Winchester

Moderate

4.7

(6)

55

hikers

Telegraph Hill – Cheesefoot Head loop from Winchester

03:07

11.5km

150m

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: July 29, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

South Downs National Park

Waypoints

A

Start point

Bus stop

1

478 m

St Giles Hill Park

Highlight • Viewpoint

Small well maintained park with gorgeous views of Winchester.
It’s worthy a short climb

Tip by

2

3.86 km

Sunset over Chilcomb

Highlight • Viewpoint

3

4.34 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

4

5.26 km

Baker & White Café

Highlight • Cafe

5

5.48 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

6

5.61 km

Pathway Through Beech Trees, South Downs National Park

Highlight • Viewpoint

A great downhill ride from Cheesefoot car park

Tip by

B

11.5 km

End point

Bus stop

Way Types & Surfaces

Way Types

4.43 km

2.02 km

2.01 km

1.73 km

1.34 km

Surfaces

5.29 km

4.80 km

1.06 km

258 m

< 100 m

< 100 m

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Elevation

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

Highest point (160 m)

Lowest point (50 m)

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Weather

Powered by Foreca

Sunday 18 October

14°C

7°C

31 %

Additional weather tips

Max wind speed: 18.0 km/h

to get more detailed weather forecasts along your route

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