Routes Planner Features Updates

Login or Signup

Login or Signup

Login or Signup

South East England

South Downs Way at Holden Farm – Cheesefoot Head loop from Winchester

South East England

South Downs Way at Holden Farm – Cheesefoot Head loop from Winchester

Moderate

17

riders

South Downs Way at Holden Farm – Cheesefoot Head loop from Winchester

01:43

25.7km

310m

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 16, 2026

Tips

Includes a segment in which cycling is not permitted

After 32 m for 76 m

Waypoints

A

Start point

Train Station

1

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

3

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

4

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

5

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

7

11.9 km

Rolling Fields Near Gander Down

Highlight • Viewpoint

8

12.5 km

South Downs Way at Holden Farm

Highlight • Cycleway

9

13.2 km

Goander Down Gravel Path

Highlight • Natural

Rolling hills and glorious singletrack

Tip by

10

15.8 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

B

25.7 km

End point

Train Station

Way Types & Surfaces

Way Types

13.7 km

5.90 km

2.33 km

2.25 km

1.46 km

Surfaces

10.8 km

10.7 km

3.52 km

580 m

< 100 m

< 100 m

Sign up to see more specific route details

Sign up for free

Elevation

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

Highest point (160 m)

Lowest point (30 m)

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Saturday 10 October

16°C

7°C

15 %

Additional weather tips

Max wind speed: 10.0 km/h

to get more detailed weather forecasts along your route

Comments

Want to know more?

Sign up for a free komoot account to join the conversation.

Sign up for free

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

Navigate Send to Phone

Move start point

Embed on a website

Report an Issue

Report restricted access

Nearby routes

4.8

89

New Forest Cycle Route: Bolderwood Loop from Lyndhurst

03:14h

36.9km

300m

4.7

4

Longcross Plain loop from Fritham — New Forest National Park

00:53h

10.3km

100m

4.9

257

Rhinefield Ornamental Drive loop from Redlynch

05:53h

102km

880m

4.8

515

Redhorn Hill Byway – Salisbury Plain Perimeter Path loop from Grateley

06:47h

98.7km

990m

5.0

104

Rhinefield Ornamental Drive loop from New Forest

01:52h

33.6km

260m

4.6

100

Meon Valley Trail – Old Winchester Hill loop from Winchester

04:47h

65.9km

980m

4.8

207

Castleman's Corkscrew Trailway loop from New Forest

02:20h

43.4km

310m

4.6

71

Beechen Lane Gravel Track – Standing Hat loop from New Forest National Park

00:53h

16.0km

120m

4.7

59

Meon Valley Trail – Meon Valley Trail loop from Wickham

02:23h

39.7km

300m

4.8

237

Birchen Hat – Poundhill Inclosure loop from Fritham

02:05h

38.6km

330m

5.0

95

Imber Perimeter Path – Imber Range Path loop from Grateley

08:16h

126km

1,330m

4.4

132

Old Winchester Hill – Meon Valley Trail loop from Petersfield

05:11h

74.9km

950m