Telegraph Hill – Cheesefoot Head loop from Winchester

Hiking trails & Routes

Telegraph Hill – Cheesefoot Head loop from Winchester

Moderate

4.5

(2)

hikers

Telegraph Hill – Cheesefoot Head loop from Winchester

03:46

13.7km

220m

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

Start point

Bus stop

Get Directions

420 m

View South to the Solent

Highlight (Segment) • Natural

3.63 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

3.64 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

4.57 km

Baker & White Café

Highlight • Cafe

4.66 km

Baker & White Coffee Co. at Cheesefoot Head Car Park

Highlight • Rest Area

Great coffee, good selection of cakes and friendly service from a vintage van. Open Thursday - Sunday
07:30 - 16:30.

Tip by

4.97 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

5.10 km

Pathway Through Beech Trees, South Downs National Park

Highlight • Viewpoint

A great downhill ride from Cheesefoot car park

Tip by

5.19 km

Great Clump

Forest

6.22 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

10.9 km

Oakclose Plantation

Forest

13.7 km

End point

Bus stop

Way Types & Surfaces

Way Types

5.91 km

5.20 km

2.53 km