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St Catherine's Hill – River Itchen loop from Winchester

Routes

Hiking trails & Routes

St Catherine's Hill – River Itchen loop from Winchester

Easy

5.0

(2)

156

hikers

St Catherine's Hill – River Itchen loop from Winchester

01:34

6.01km

40m

Hiking

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: May 9, 2026

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Your route passes through protected areas

Please check local regulations for:

South Downs National Park

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865 m

Hospital of St Cross

Highlight • Religious Site

The Hospital of St CrossClick to open side panel for more information is a hidden gem in Winchester that feels like stepping through a time portal. Located about a twenty-minute walk from the city center along the scenic River Itchen water meadows, it is often described as England's "oldest and most perfect" almshouse. It’s not a hospital in the modern sense but a medieval charitable institution that still houses 25 "Brothers" today.

The atmosphere is incredibly tranquil, characterized by flint-walled buildings, quiet quadrangles, and a sense of living history that has remained largely unchanged for centuries.

The Wayfarer's Dole: One of the most charming traditions you can experience is requesting the "Dole" at the Porter’s Lodge. For nearly 900 years, any traveler who asks is given a small horn cup of ale and a morsel of white bread—a custom started by a Cluniac monk to support pilgrims.

The "Miniature Cathedral": The onsite church is far grander than a typical chapel, featuring massive stone walls and beautiful Norman "chevron" carvings. Visitors often mention the peaceful, spiritual vibe inside, and some even suggest lying on the floor in the center to appreciate the "sacred geometry" of the architecture.

The Gardens: You can wander through the Master’s Garden and the Compton Garden, which were inspired by 17th-century botanical collections. They feature sculptural borders, old-fashioned roses, and a large carp pond, all set against the backdrop of St Catherine's Hill.

The Hundred Men’s Hall: This 14th-century hall, where a hundred poor men were once fed daily, now serves as a cozy tearoom. It’s run by volunteers and is famous for its homemade cakes, artisan sausage rolls, and "legendary" buns from a local bakery.

The Brothers: You might see the residents walking around in their traditional medieval-style gowns—black for the original order and claret (dark red) for the "Noble Order of Poverty."

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1.24 km

View of the Hospital of St Cross

Highlight • Viewpoint

The Hospital of St Cross is said to be England's oldest charitable institution. It was founded by Henry of Blois between 1132 and 1136 after he was appointed Bishop of Winchester at the age of 28. It was created in order to house and support 13 poor men, known as Brothers, and to feed a further 100 men at its gates each day, with food and drink from the hospital's own land, mills and farms. In 1445 another Order of Brothers was created by Cardinal Henry Beaufort, the Order of Noble Poverty. Today the Hospital is home to 25 'Brothers'.

Built with stone from as far afield as Caen, the church consists of stunning honey coloured Norman stonework both inside and out. On a column on the north aisle is carved the cross of St Cross. In the window nearest to the eastern side of the north transept, the stone surround is strangely angled. This device means that sunlight from the window falls on the cross only on 3rd May (the day in the church calendar of the Invention of the Cross) and 14th September (Holy Cross Day).

nationalchurchestrust.org/church/hospital-st-cross-winchester

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2.80 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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2.87 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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3.74 km

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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3.84 km

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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