winchester logo

Winchester Group

We are the Winchester Ramblers. We open the way for everyone in our local community to enjoy the pleasures of walking.

Join the Ramblers and enjoy

  • unlimited free access to 50,000 Ramblers group walks
  • a library jam-packed with thousands of tried-and-tested routes
  • a welcome pack teeming with top tips plus our Walk magazine
  • exclusive discounts from our partners
  • knowing your support is opening up more places to walk and helping more people discover the joy of walking
1 of 0

Overview

From the start the view over Mattingley Bowl is a most impressive spot which must have been a tense place when Eisenhower addressed troops the day before D Day and this in stark contrast to the hedonistic use for the Boomtown Festival in August each year.  

We take the South Downs Way before taking a very minor road near Gander Down and then we walk further along the undulating South Downs as we take in panoramic views and after a descent have a final climb back to Cheesefoot Head.

Monday, 28 July 2025
Start time:
6:00 pm
Estimated finish time:
8:30 pm
Difficulty:
Moderate
Distance:
8km / 5.0mi
Ascent:
149.4m / 490ft
Type:
circular

Features

  • Car parking available

Starting point

Grid reference:
SU 52928 27724
Nearest postcode:
SO21 1HW
what3words:
florists.second.gravel
Start time:
6:00 pm

Cheesefoot Head CP is free at the time of writing. There is parking for 20 or so cars but it is a popular CP so car sharing is recommended.

Join the Ramblers and enjoy

  • unlimited free access to 50,000 Ramblers group walks
  • a library jam-packed with thousands of tried-and-tested routes
  • a welcome pack teeming with top tips plus our Walk magazine
  • exclusive discounts from our partners
  • knowing your support is opening up more places to walk and helping more people discover the joy of walking