15 Short Walks Winchester

Discover the timeless charm of Winchester and its surrounding countryside with this collection of 15 carefully curated short walks, showcasing the city’s historic landmarks, chalk downlands, vibrant villages, and sparkling clear streams.

Each route is designed to be completed in under three hours (ranging from 3 to 11km), making this guidebook the perfect companion for families, newcomers, and anyone eager to explore the best of Hampshire’s heartland at a relaxed pace.

• Each of the 15 walks features clear, easy-to-follow Ordnance Survey maps alongside step-by-step route descriptions, with practical information on facilities, parking, and route highlights to ensure every outing is enjoyable, accessible, and well-planned.
• Discover the region’s most memorable sights, from the soaring Winchester Cathedral, the tranquil riverside of Keat’s Walk, and the historic Hockley Viaduct to the ancient ramparts of St Catherine’s Hill, Wolvesey Castle, and idyllic villages like Ovington and Easton.
• Routes begin from Winchester and welcoming neighbouring towns and villages, including New Alresford, Stockbridge, and Cheriton, with options for public transport and car-free access for many walks.
• Experience Hampshire’s unique chalk landscape, abundant wildlife, and rich history, with walks that take in Sites of Special Scientific Interest such as Stockbridge Down and Chilbolton Cow Common, as well as the internationally renowned chalk streams of the Itchen, Meon, and Test.
• Accommodation advice is included for Winchester, New Alresford, and Stockbridge, from characterful inns to comfortable hotels, ideal for extending your stay amid Hampshire’s rolling hills and historic market towns.

Part of Cicerone’s trusted Short Walks series, this guide to Winchester brings together everything you need for a memorable day out in one of England’s most picturesque and historic regions. Whether you’re a local resident, a day visitor, or planning a scenic getaway, this guide is your key to discovering the best of Winchester and the Hampshire countryside at an easy, enjoyable pace.

Seasons

Suitable for year-round walking. A small section of Walk 9 can be quite muddy and in winter some of the other routes will also have short sections that are muddy.

Centres

Winchester, New Alresford, Hinton Ampner, Ovington, Avington, Stockbridge, Wherwell, Easton, Shawford, Itchen Abbas, Micheldever, Hunton, Longparish

Difficulty

All the routes are straightforward and no special equipment or challenging navigation is required. Only four of the routes have a stile to negotiate. The level of fitness required is modest apart from Walk 5 which includes a short but sharp ascent up to St Giles Hill.

Must See

The Cathedral, Kingsgate, Keats’ Walk, St Cross Almshouse, Hockley Viaduct, St Catherine’s Hill, Wolvesey Castle, The Itchen by the Weirs in Winchester, Statue of King Alfred the Great, St Giles Hill viewing platform, South Downs Way, City Mill, Westgate, Hinton Ampner, Watercress Heritage Line, New Alresford, Ovington, Stockbridge Down, Stockbridge including the dismantled Sprat and Winkle railway, Wherwell

Map key

Overview map

Using this guide

Route summary table

Introduction

Walking in Winchester and the surrounding area

Places to stay

Travel to and from Winchester

The walks

1. Winchester Cathedral, St Cross and Tun Bridge

2. St Catherine’s Hill, Hockley Viaduct and Kingsgate

3. Hyde Gate, Kings Worthy, Abbots Worthy and Easton

4. Chilcomb and the South Downs Way

5. City Mill, St Giles Hill and Wolvesey Castle

6. Westgate, St Cross and Shawford

7. Cheriton, Hinton Ampner and Kilmeston

8. New Alresford, Abbotstone and Old Alresford

9. Itchen Stoke and Ovington

10. Itchen Abbas, Martyr Worthy, Easton and Avington

11. Stockbridge Down

12. Stockbridge and Houghton

13. Micheldever, Stoke Charity, Hunton and Wonston

14. Wherwell and Chilbolton Cow Common

15. Longparish

Useful information