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Wheely Down Farm Lane – Cheesefoot Head loop from Winchester

Wheely Down Farm Lane – Cheesefoot Head loop from Winchester

Moderate

4.7

(3)

riders

Wheely Down Farm Lane – Cheesefoot Head loop from Winchester

02:11

33.6km

390m

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: June 20, 2026

Tips

Includes a segment in which cycling is not permitted

After 32 m for 76 m

Waypoints

Start point

Train Station

Get Directions

1.35 km

Winchester City Mill – Start or End of the South Downs Way

Highlight • Trail

Winchester City Mill is the official ‘gateway’ into the South Downs National Park, and marks the start (or end) or the South Downs Way.

Tip by

5.76 km

Chilcomb Wood

Forest

6.49 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

6.80 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

8.06 km

Pathway Through Beech Trees, South Downs National Park

Highlight • Viewpoint

A great downhill ride from Cheesefoot car park

Tip by

8.15 km

Great Clump

Forest

16.5 km

Wheely Down Farm Lane

Highlight • Trail

Wheely Down Farm Lane is a fabulous road with wonderful ridge top views as far as the English Channel.

It runs parallel to the route of the South Downs Way, …

Tip by

16.6 km

View of the South Downs Landscape

Highlight • Viewpoint

Make sure to visit one of the many restaurants or pubs in the area... They are very good.

Tip by

21.2 km

Goander Down Gravel Path

Highlight • Natural

Rolling hills and glorious singletrack

Tip by

23.8 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

33.6 km

End point

Train Station

Way Types & Surfaces

Way Types

16.7 km

10.3 km

2.82 km

2.33 km

1.46 km

Surfaces

15.9 km

12.4 km

4.66 km

580 m

< 100 m

Elevation

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

Highest point (170 m)

Lowest point (30 m)

Weather

Friday 26 June

28°C

16°C

0 %

Additional weather tips

Max wind speed: 17.0 km/h

to get more detailed weather forecasts along your route

Comments

August 27, 2021,The South Downs Way - Part 1

A quick snack in Winchester after leaving the station and then we got going. Only a short spin, just enough to get us on the route and set us up for an easy start on day 2.

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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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Wheely Down Farm Lane – Cheesefoot Head loop from Winchester

Winchester City Mill – Start or End of the South Downs Way

Chilcomb Climb

View of Cheesefoot Head and Wildflower Fields

Pathway Through Beech Trees, South Downs National Park

Wheely Down Farm Lane

View of the South Downs Landscape

Goander Down Gravel Path

Cheesefoot Head

Nearby routes

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