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Routes
Hiking trails & Routes
United Kingdom
England
South East England
Hampshire
Winchester
Itchen Valley

Cheesefoot Head and Owslebury Loop

Hard

4.7

(3)

12

hikers

Cheesefoot Head and Owslebury Loop

05:58

21.8km

330m

Hiking

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

Last updated: February 26, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

South Downs National Park

Waypoints

A

Start point

Parking

Get Directions

1

315 m

Cheesefoot Head

Highlight • Natural Monument

The large natural amphitheatre of Cheesefoot Head marks the first great view you experience along the South Downs Way, with views stretching to the Solent and the Isle of Wight. …

Tip by

5.13 km

Public Water Fountain

Public Water Fountain

3

12.3 km

Green Hill Summit

Highlight • Trail

In the western reaches of the South Downs National Park, Green Hill stands at 423 feet (129 m) high with a trig point at the summit. From the lane at …

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15.2 km

Public Water Fountain

Public Water Fountain

5

15.2 km

St Andrew's Church, Owslebury

Highlight • Historical Site

This picturesque church sits in the village of Owslebury and has done since the 14th century. On the western edge of the South Downs National Park, the surroundings are as …

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B

21.8 km

End point

Parking

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Way Types & Surfaces

Way Types

7.04 km

5.12 km

4.57 km

2.29 km

1.89 km

910 m

Surfaces

8.47 km

4.89 km

3.86 km

2.38 km

1.86 km

363 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (170 m)

Lowest point (50 m)

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Weather

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Today

Sunday 24 May

31°C

15°C

0 %

Additional weather tips

Max wind speed: 15.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to complete this loop?

This is a challenging hike, and komoot estimates it takes approximately 6 hours to complete the full 21.8 km (13.5 miles) loop. However, your actual duration may vary depending on your pace, fitness level, and stops for breaks or enjoying the views.

What is the terrain like on this hike?

The terrain primarily consists of rolling chalk downlands, with a mix of open meadows and ancient woodlands. You'll encounter gentle ascents leading to modest hills, like Green Hill Summit, and descents into valleys. Some paths are along quiet lanes and bridleways, while others traverse fields. Be prepared for potentially muddy sections, especially after rain, so sturdy hiking boots are highly recommended.

Is this route suitable for beginners?

Given its difficult rating, distance of nearly 22 km, and over 300 meters of elevation gain, this route is not recommended for beginners. It requires a reasonable to very good level of fitness. There are shorter, easier walks in the wider Cheesefoot Head area if you're looking for a less challenging option.

Where can I park to start the hike?

While the specific starting point for this komoot Tour is near Chilcomb, many routes in the area offer parking. Cheesefoot Head itself has parking facilities. Alternatively, you might find parking options in Owslebury, which can also serve as a convenient starting point, especially if you plan to visit local pubs.

Is the trail dog-friendly?

Yes, the trails around Cheesefoot Head and Owslebury are generally dog-friendly. However, as you'll be passing through farmland and potentially near livestock, it's crucial to keep dogs under close control, preferably on a leash, to protect wildlife and farm animals. Always follow the Countryside Code.

When is the best time of year to hike this route?

The trails offer beautiful scenery year-round. Spring brings wildflowers and lush greenery, while autumn showcases vibrant foliage. Summer provides longer daylight hours, but paths can be exposed. Winter walks are possible, especially on chalk-land paths, but be prepared for mud and potentially colder, shorter days. Always check weather conditions before you go.

Are there any permits or fees required to hike here?

No, there are no specific permits or entrance fees required to hike this route or access the general public footpaths in the South Downs National Park. However, standard countryside access rules apply, and you should respect private land and follow signage.

What notable landmarks or viewpoints will I see along the way?

You'll encounter several interesting points, including the natural amphitheater of Cheesefoot Head, and the modest ascent to Green Hill Summit. The route also passes by St Andrew's Church, Owslebury. You'll enjoy expansive views across the South Downs National Park, the Itchen Valley, and on clear days, even glimpses of the Isle of Wight.

Does this route connect with other long-distance trails?

Yes, this route utilizes sections of several well-known paths. You'll find yourself on parts of the King Alfred's Way, the South Downs Way, the Monarch's Way, and the Pilgrims' Trail, offering a taste of these historic long-distance routes.

Are there any pubs or cafes near the trail?

Yes, the village of Owslebury, which is part of this loop, has local pubs such as The Ship pub, where you can stop for refreshments. The nearby village of Chilcomb is also very pretty, though smaller.

Are there specific regulations for hiking in South Downs National Park?

As part of the South Downs National Park, hikers are encouraged to follow the Countryside Code. This includes sticking to marked paths, keeping dogs under control, taking all litter home, and respecting wildlife and livestock. There are no specific permits or fees for hiking public rights of way within the park.

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