Cheesefoot Head – Westgate, Winchester loop from Littleton and Harestock

Routes

Bike touring routes & trails

Cheesefoot Head – Westgate, Winchester loop from Littleton and Harestock

Hard

riders

Cheesefoot Head – Westgate, Winchester loop from Littleton and Harestock

03:32

47.8km

460m

Cycling

Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route. The starting point of the route is accessible with public transport.

Last updated: August 19, 2026

Tips

Includes a segment in which cycling is not permitted

After 21.2 km for 78 m

Waypoints

Start point

Bus stop

Get Directions

20.0 km

Watercress Beds

Highlight • Other

Historic waterbeds for growing watercress, on a very quiet road. There's a ford just along with a perfect cycle crossing

Tip by

30.2 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

31.3 km

Great Clump

Forest

31.3 km

Boomtown Festival Site View

Highlight • Viewpoint

Good access to the South Downs Way.

Tip by

31.9 km

Cheesefoot Head

Highlight • Natural Monument

Great lookout over the Matterley Bowl, a natural amphitheatre.

Tip by

34.0 km

Chilcomb Wood

Forest

38.4 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

38.5 km

Statue of King Alfred the Great, Winchester

Highlight • Historical Site

Winchester’s statue of Alfred the Great is one of the city’s most iconic sights. He stands at the bottom of The Broadway next to the River Itchen and the Guildhall, …

Tip by

38.5 km

Winchester Guildhall

Highlight • Monument

Winchester is packed to the rafters with phenomenal buildings, each worth seeking out and seeing for yourself. The Guildhall is particularly magnificent and stands near the bottom of the High …

Tip by

39.3 km

Westgate, Winchester

Highlight • Historical Site

This is the Westgate and it contains a tiny museum which you should visit when open. You can also step outside at the top to enjoy a view down the High Street.

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