St Catherine's Hill – Hockley Viaduct loop from Winchester

Hiking trails & Routes

St Catherine's Hill – Hockley Viaduct loop from Winchester

Easy

5.0

(1)

hikers

St Catherine's Hill – Hockley Viaduct loop from Winchester

00:58

3.75km

20m

Hiking

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: August 23, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

South Downs National Park

Waypoints

Start point

Parking

Get Directions

109 m

The Handlebar Café

Highlight • Cafe

Open every day and they have a small ice cream bicycle in the car park below.

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209 m

The Boys With the Kite Mural by Hendog

Highlight • Monument

Hendog is a street artist whose identity is unknown. There are a number of paintings by him/her in the city. For more information see Hendog.art
This mural is called “The boys with the Kite” and is located near a small free parking lot.

Translated by Google •

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233 m

The Itchen Way

Highlight • River

A cycle route that runs alongside the River Itchen south of Winchester and forms part of the National Cycle Route 23, to Southampton.

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238 m

Viaduct Way – St Catherine's Hill

Highlight (Segment) • Trail

Have a rest and enjoy the view at The Handle Bar Cafe google.co.uk/maps/place/Cadence+at+The+Handlebar+Cafe/@51.0493993,-1.3137403,445m/data=!3m1!1e3!4m6!3m5!1s0x48740d88c43c7b53:0xc09946315b116c5f!8m2!3d51.0493875!4d-1.3112148!16s%2Fg%2F11fn6mp69f?entry=ttu&g_ep=EgoyMDI0MTExOC4wIKXMDSoASAFQAw%3D%3D

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1.02 km

Start of South-West Steps to St Catherine’s Hill

Highlight • Trail

The iconic, but deteriorating, wooden steps on the main path up St Catherine's Hill have recently been replaced by the Hampshire & Isle of Wight Wildlife Trust as part of a crucial refurbishment project. The new steps are constructed from durable, anti-slip treated timber to provide a safer, more stable, and more sustainable route for visitors, with an expected lifespan of at least 30 years. This essential conservation work is designed not only to improve public access to the historic Iron Age hillfort but also to safeguard the site's fragile chalk grassland and biodiversity by preventing visitors from creating unsanctioned, damaging paths.

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1.08 km

St Catherine's Hill

Highlight • Viewpoint

The pathway up is unclear from this point. Note however that there is an easy to follow route up with mostly steps on the south west side of the hill

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2.04 km

Hockley Viaduct

Highlight • Bridge

Walk or cycle along Winchester’s restored historic railway.
Opened in 1891, the Hockley Viaduct was part of the Didcot to Southampton railway. It closed to passengers in 1960, and to freight in 1966 as part of the national programme of closures proposed by Dr Richard Beeching.

The viaduct has now been repaired to begin a new life as part of the National Cycle Route Network Route 23, for walkers and cyclists to enjoy. Take the Viaduct Way and enjoy some scenic views from a lovingly restored landmark.

visitwinchester.co.uk/listing/viaduct-way-trail

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2.23 km

Hockley Viaduct

Highlight • Bridge

Originally called the Shawford Viaduct, this 19th-century railway viaduct to the south of Winchester ceased operating as a railway link in 1966 and is now open to walkers and cyclists as part of National Cycle Network Route 23.

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