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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
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Overview

Leaving Winchester along the first few miles of the South Downs Way, and taking in the panoramic views from the heights of Cheesefoot Head, we will continue on a picturesque 13 mile loop across Gander Down to the South East of Winchester, returning via the Pilgrim's Way.  This is a mixed downland and woodland hike, along ancient paths and trackways through a beautiful part of Hampshire.

Please note the 9.30am Start Time for this walk

Monday, 17 November 2025
Start time:
9:30 am
Estimated finish time:
3:00 pm
Difficulty:
Moderate
Distance:
20.9km / 13.0mi
Ascent:
345.9m / 1135ft
Type:
circular

Expect a brisk pace on this hike, with a significant early ascent up to Cheesefoot Head, and a couple of lesser climbs later on.  There are no facilities along the way, so bring a flask and picnic lunch as well as a bottle of water, and dress for the weather as there are some long exposed sections high on the South Downs.  Bring your poles if you have them, as they will be handy on the uphill and slightly slippy bits.

Please let the walk leader know if you are coming on this hike, or if you have any questions.

Features

  • Accessible by public transport
  • Car parking available
  • Car sharing available
  • Dog friendly
  • No car needed
  • No Stiles

Starting point

Grid reference:
SU 48806 28242
Nearest postcode:
SO23 8RA
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Start time:
9:30 am

East Winchester (St Catherine's) Park and Ride at Bar End, meeting by the coach stop and toilet block. There are regular Park and Ride buses running from the centre of Winchester to and from here, and all day parking is available for £3.50

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