Chilcomb & Itchen Valley loop from Winchester — South Downs National Park

Hiking trails & Routes

Chilcomb & Itchen Valley loop from Winchester — South Downs National Park

Hard

4.6

(10)

hikers

Chilcomb & Itchen Valley loop from Winchester — South Downs National Park

06:54

26.0km

260m

Hiking

Embark on a difficult 16.2-mile (26.0 km) hike through the Chilcomb & Itchen Valley loop, a journey that blends rolling chalk downs with tranquil riverside paths. You will gain 842 feet (257 metres) in elevation over approximately 6 hours and 54 minutes, experiencing varied terrain and expansive views. From points…

Last updated: April 23, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

South Downs National Park

Waypoints

Start point

Parking

Get Directions

4.32 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

5.47 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

11.9 km

Tichborne's thatched cottages

Highlight • Historical Site

Tichborne manor was given to the Bishop of Winchester by Edward the Elder over a thousand years ago and the village has become populated with a glorious cluster of historic …

Tip by

17.3 km

Avington Park Mansion

Highlight • Historical Site

Avington Park is a grand, 16th-century house that lies in stunning parkland. The Grade I-listed mansion underwent significant renovation and construction in the 17th century and again in the 18th …

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26.0 km

End point

Parking

Way Types & Surfaces

Way Types