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United Kingdom
England
South East England
Hampshire

Chilcomb Climb – Cheesefoot Head loop from Winchester

Routes
United Kingdom
England
South East England
Hampshire

Chilcomb Climb – Cheesefoot Head loop from Winchester

Moderate

4

riders

Chilcomb Climb – 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: March 27, 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

A

Start point

Bus stop

Get Directions

1

4.02 km

National Cycle Network Route 89 Marker

Highlight • Cycleway

Always reassuring to see these en route!

Tip by

2

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

3

4.95 km

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

Tip by

4

4.96 km

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

5

6.15 km

View of Boomtown Festival Grounds

Highlight • Viewpoint

6

6.21 km

Boomtown Festival Site View

Highlight • Viewpoint

Good access to the South Downs Way.

Tip by

7

6.22 km

A great downhill ride from Cheesefoot car park

Tip by

8

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

B

14.7 km

End point

Bus stop

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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

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Elevation

Elevation

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

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Weather

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Saturday 20 June

29°C

13°C

-- %

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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