Cheesefoot Head – Cheesefoot Head loop from Winchester

Cheesefoot Head – Cheesefoot Head loop from Winchester

Moderate

riders

Cheesefoot Head – Cheesefoot Head loop from Winchester

00:58

14.7km

180m

Gravel riding

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: September 24, 2026

Tips

Cycling is not permitted along parts of this route

After 924 m for 68 m

After 13.7 km for 68 m

Waypoints

Start point

Bus stop

Get Directions

4.02 km

National Cycle Network Route 89 Marker

Highlight • Cycleway

Always reassuring to see these en route!

Tip by

4.65 km

Chilcomb Climb

Highlight • Trail

An unforgettable climb at the start of the SDW - you’ll really start to understand what you’re in for at this stage 😄

Tip by

4.95 km

View of the Hampshire Countryside from South Downs National Park

Highlight • Viewpoint

Great views looking north of Hampshire countryside.
Nice long stretch of gravel track.

Tip by

4.96 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

6.09 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

6.21 km

Boomtown Festival Site View

Highlight • Viewpoint

Good access to the South Downs Way.

Tip by

6.22 km

Pathway Through Beech Trees, South Downs National Park

Highlight • Viewpoint

A great downhill ride from Cheesefoot car park

Tip by

7.36 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 …

Tip by

14.7 km

End point

Bus stop

Way Types & Surfaces

Way Types

7.27 km

3.14 km

1.77 km

1.31 km

1.23 km

Surfaces

7.03 km

5.87 km

1.82 km

Elevation

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

Weather

Saturday 10 October

17°C

7°C

18 %

Additional weather tips

Max wind speed: 8.0 km/h

to get more detailed weather forecasts along your route

Comments

March 15, 2025,South Downs Way - exploring Terry Pratchett country

Out-and-back 24K (mobile ran out of charge). Steep uphills, and quite flinty and skiddy on the downhills. Beautiful though. Will never stop looking for Feegles in places like this.