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Routes
Hikes
United Kingdom
England
South East England
Hampshire
Winchester

Chilcomb

The best walks and hikes around Chilcomb

4.6

(1224)

11,716

hikers

579

hikes

Hiking around Chilcomb explores the rolling chalk downs and river valleys within the South Downs National Park. The landscape is characterized by its chalk geology, creating a varied terrain of grassy hills with expansive views and gentle paths along the River Itchen. Many routes incorporate sections of the South Downs Way national trail, passing historical sites like Cheesefoot Head and natural landmarks such as St Catherine's Hill. The area offers a blend of serene riverside walks and challenging hill climbs.

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Last updated: May 6, 2026

5.0

(2)

11

hikers

#1.

Cheesefoot Head and Owslebury Loop

21.8km

05:58

330m

330m

Hike the difficult 13.6-mile Cheesefoot Head and Owslebury Loop in South Downs National Park, gaining 1078 feet over varied terrain.

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Hard

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Popular around Chilcomb

South Downs National Park – A Walk in the Parks

Road Cycling Routes around Chilcomb

Running Trails around Chilcomb

Cycling around Chilcomb

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South Downs National Park – A Walk in the Parks

Hiking Collection by

Jen Lowthrop

Tips from the Community

Sylkeweb
July 9, 2025, Wharf Mill

A Grade II Listed Building at the River Itchen. β€œAt the head of the Itchen Navigation Canal, and once the city's principal grain mill. A mill has been on this site since the 12th century, but the present building dates from 1885. The South Downs Way passes in front of the building.” https://www.geograph.org.uk/photo/1893591 β€œA water-powered corn mill in the historic county of Hampshire, England.” https://new.millsarchive.org/mills/index/?which=3476

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Beautiful views on this section of the SDW.

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Super useful spot mid-ride but can be easily missed!

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Good access to the South Downs Way

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Good access to the South Downs Way.

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Open views and wild flowers surrounding the gravel track in July time of year.

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Nice to have good highlights pointing out the water stops on the SDW.

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Frequently Asked Questions

Are there any easy, family-friendly walks near Chilcomb?

Yes, the area offers many gentle routes suitable for families. For a very accessible and historic walk, consider the Winchester Cathedral – The Weirs, Winchester loop from Bar End. It's a relatively flat, 5-km walk that follows the scenic River Itchen and is perfect for a short outing with kids.

Where can I find the best scenic views on a hike?

For some of the most expansive views, head to Cheesefoot Head. This large natural amphitheater offers stunning panoramic vistas across the South Downs, and on a clear day, you can see as far as the Solent and the Isle of Wight. Many trails in the area incorporate this viewpoint.

Are the hiking trails around Chilcomb dog-friendly?

Generally, yes. The public footpaths and bridleways in the South Downs National Park are great for walking with dogs. However, you will be walking through farmland with livestock, so always keep your dog on a lead in these areas. Also, be mindful of ground-nesting birds, especially during spring and early summer.

What do other hikers think of the trails around Chilcomb?

The trails are very popular with the komoot community, which has given the area an average rating of 4.6 stars. Hikers often praise the classic English countryside scenery, the rolling chalk hills, and the well-maintained paths along sections of the South Downs Way.

How many hiking trails are available around Chilcomb?

You have a wide variety of options to choose from. There are nearly 600 hiking routes around Chilcomb, ranging from short, easy strolls to challenging all-day treks across the South Downs.

Are there any challenging hikes in the area?

Yes, for those seeking a more strenuous hike, there are several options. The The Weirs, Winchester – Cheesefoot Head loop from Chilcomb is a great example. It's a 20.5 km route with significant elevation gain that provides a rewarding challenge with beautiful scenery.

Can I walk from Chilcomb to Winchester?

Absolutely. Several paths connect Chilcomb to the historic city of Winchester. You can follow a section of the South Downs Way, which offers a scenic route over the chalk downland. The walk allows you to experience the transition from rural landscapes to the city's edge.

What kind of wildlife might I see on the trails?

The chalk grassland is a special habitat supporting a variety of wildflowers, including orchids, and numerous butterfly species like the chalkhill blue. Along the River Itchen, you can often spot swans and ducks. Keep an eye out for red kites and buzzards soaring over the downs.

Are there any circular walks available?

Yes, circular walks are very common in the Chilcomb area. Many routes are designed as loops that start and end at the same point, allowing you to explore the region without needing to retrace your steps. The Gander Down – Cheesefoot Head loop from Hampshire is a popular moderate circular route.

What historical points of interest can I see while hiking?

The landscape is rich in history. You can see prehistoric field systems and burial mounds, such as the bowl barrow on Telegraph Hill. The village of Chilcomb itself has a Norman church, St. Andrew's, dating back to the 12th century. Many trails pass by these historic landmarks.

Where is a good place to park for a hike?

While Chilcomb village has limited parking, many hikers start from larger car parks in the area. The car park at Cheesefoot Head is a very popular starting point for several trails. Alternatively, you can park in one of the car parks in Winchester, such as at Bar End, and begin your walk from there.

Are there any hikes that include a stop for a pub or cafe?

Yes, you can easily combine a walk with a refreshment stop. For example, the Baker & White CafΓ© loop from Chilcomb is a pleasant walk designed around a cafe stop. Additionally, many routes that start or finish in Winchester offer numerous options for pubs and cafes.

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