Cheesefoot Head – Telegraph Hill loop from Cheriton

Running trails & routes

Cheesefoot Head – Telegraph Hill loop from Cheriton

Moderate

5.0

(1)

runners

Cheesefoot Head – Telegraph Hill loop from Cheriton

01:31

14.2km

200m

Running

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Last updated: July 17, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

South Downs National Park

Waypoints

Start point

Get Directions

721 m

Bench With a View of South Downs

Highlight • Viewpoint

4.80 km

Pathway Through Beech Trees, South Downs National Park

Highlight • Viewpoint

A great downhill ride from Cheesefoot car park

Tip by

4.93 km

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

6.05 km

View of Cheesefoot Head and Wildflower Fields

Highlight • Natural

This is a beautiful part of the South Downs Way close to Telegraph Hill near to the village of Chilcomb. It offers stunning views out towards Winchester and is home to a variety of wildflowers in summer months, including poppies.

Tip by

6.07 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

7.10 km

Chilcomb Wood

Forest

9.08 km

Cheesefoot Head

Highlight (Segment) • Historical Site

Cheesefoot Head is a natural amphitheatre and beauty spot that provides sweeping vistas of the South Downs.

The area holds historical significance as well. During World War II, it served as an important military training area for British troops preparing for the D-Day invasion in Normandy. You can still spot remnants of military training, adding to its historical interest.

Tip by

10.6 km

Water Pumps and Cycle Tool Kit at South Downs Way

Highlight • Cycleway

Fresh water tap - an essential resource for South Downs Way walkers and cyclists. Tap tested and working in May 2022. This station also includes a bike pump/tools.

Tip by

14.2 km

End point

Way Types & Surfaces

Way Types

13.6 km

246 m

238 m

Surfaces

7.00 km

6.56 km

559 m