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United Kingdom
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Gloucestershire
Tewkesbury
Winchcombe

Cleeve Hill loop from Winchcombe

Moderate

4.7

(34)

210

hikers

Cleeve Hill loop from Winchcombe

04:00

14.2km

280m

Hiking

Embark on the Cleeve Hill loop from Winchcombe, a moderate hiking route that spans 8.8 miles (14.2 km) with an elevation gain of 905 feet (276 metres). This journey, estimated to take 3 hours and 59 minutes, leads you from the charming Winchcombe Village through tranquil farmland and lush meadows.…

Last updated: April 23, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

The Cotswolds National Landscape

Waypoints

A

Start point

Parking

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1

383 m

Winchcombe Village

Highlight • Settlement

The ancient Anglo Saxon town of Winchcombe is situated between Broadway and Cheltenham. In the early 17th century, the Winchcombe area was renowned for growing tobacco and was banned from …

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2

3.60 km

Belas Knap Long Barrow

Highlight • Historical Site

Belas Knap is an example of a Neolithic long barrow, with a false entrance and side chambers. Excavated in 1863 and 1865, the remains of 31 people were found in …

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3

8.79 km

Summit view from Cleeve Hill

Highlight • Natural Monument

At 1,083 feet (330 m) above sea level, Cleeve Hill is the highest point in Gloucestershire and the highest peak of the Cotswold Hills. It's part of Cleeve, which is …

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B

14.2 km

End point

Parking

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Way Types & Surfaces

Way Types

6.70 km

4.56 km

1.47 km

1.41 km

< 100 m

Surfaces

6.30 km

2.48 km

1.92 km

1.91 km

971 m

632 m

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Elevation

Elevation

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Highest point (330 m)

Lowest point (90 m)

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Weather

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Tuesday 5 May

14°C

5°C

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park for the Cleeve Hill loop from Winchcombe?

The trail typically starts and ends in the picturesque town of Winchcombe. You can usually find parking in Winchcombe itself, which is recognized as a 'Walkers are Welcome' town. Specific parking details might vary, so it's always a good idea to check local signage upon arrival.

How challenging is the Cleeve Hill loop from Winchcombe?

This loop is generally rated as moderate in difficulty. The main challenge is the steep climb up Cleeve Hill, which requires a moderate level of fitness. While the ascent is steady, it can be particularly slippery in wet conditions. The varied terrain includes well-trodden paths, rugged sections, and open hilltops.

What is the terrain like on the Cleeve Hill loop, and what should I wear?

The terrain is quite diverse, ranging from tranquil farmland and meadows to rolling hills and quiet woodlands. Sections can be very muddy, especially after rain. You'll also traverse Cleeve Common with its unique limestone grassland. Sturdy, waterproof hiking boots are highly recommended, and layers of clothing are advisable due to changing conditions and exposure on the hilltops.

What are the main points of interest and viewpoints along the route?

The route offers several highlights. You'll pass through Winchcombe Village, encounter the ancient Belas Knap Long Barrow, and enjoy superb panoramic views from the Summit view from Cleeve Hill. On a clear day, these vistas can extend over the River Severn, into Wales, and include the Malvern Hills and even the Black Mountains.

Is the Cleeve Hill loop from Winchcombe dog-friendly?

Yes, the trail is generally dog-friendly. However, much of the walk traverses Cleeve Common, which is home to grazing sheep and cattle. It is essential to keep dogs under close control, preferably on a leash, especially when near livestock, to ensure their safety and the well-being of the animals.

What is the best time of year to hike the Cleeve Hill loop from Winchcombe?

Spring and summer are particularly rewarding, as Cleeve Common's limestone grassland is rich in wildflowers and butterflies. However, the trail can be enjoyed year-round. Be aware that sections can be very muddy in wet conditions, and winter can bring colder, potentially icy, or snowy weather, requiring appropriate gear.

Are there any permits or entrance fees required for this trail or the Cotswolds AONB?

No, there are no specific permits or entrance fees required to hike this loop or to access the Cotswolds Area of Outstanding Natural Beauty (AONB). The trails are freely accessible to the public, though visitors are encouraged to follow the Countryside Code and respect private land.

Does this loop connect with other popular hiking trails?

Yes, the route incorporates significant sections of the famous Cotswold Way National Trail. It also overlaps with parts of the Winchcombe Way, Gustav Holst Way, and the National Byway, offering opportunities to explore further if you wish.

Is this trail suitable for families with children?

While the full loop is rated moderate due to the steep climb and distance, shorter, easier routes of about 4 miles are available, featuring mostly level sections. Families with older children or those accustomed to hiking might enjoy the full loop, but younger children might find the ascent challenging. Consider the shorter options for a more family-friendly experience.

Are there any pubs or cafes near the trail for refreshments?

Winchcombe, being the starting and ending point, is a charming town with historic buildings and offers various options for refreshments, including pubs and cafes. It's a great place to relax and refuel before or after your hike.

What's a local tip for making the most of the Cleeve Hill views?

For truly unparalleled 360-degree views, make sure to seek out 'The Single Beech' (also known as the lonely beech) on Cleeve Common. It's the highest tree in the Cotswolds and offers exceptional vistas across the landscape, making it a perfect spot for a break and photos.

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