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Routes
Mountain biking trails
United Kingdom
England
South West England
Dorset
East Dorset
Sixpenny Handley And Pentridge

Win Green and Cranborne Droves Way Loop

Moderate

12

riders

Win Green and Cranborne Droves Way Loop

03:05

35.0km

530m

Mountain biking

Ride the moderate 21.7-mile Win Green and Cranborne Droves Way Loop for panoramic views and varied terrain on ancient droving routes.

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Cranborne Chase & West Wiltshire Downs AONB

Waypoints

A

Start point

Parking

Get Directions

1

7.93 km

Ox Drove Road (Cranborne Droves Way Trail)

Highlight • Viewpoint

The old drove roads have been here for thousands of years providing the safest way of travelling and moving cattle across the land. This road was probably used to move …

Tip by

2

13.4 km

Win Green Summit

Highlight • Historical Site

Win Green is the highest point in the Cranborne Chase and affords breathtaking panoramic views over Blackmore Vale and the Salisbury Plain. The views even stretch to the Isle of …

Tip by

3

18.4 km

White Sheet Hill

Highlight (Segment) • Summit

This is the byway from the A30 at about 140m to the top of White Sheet Hill where there is a trig point at 242m, 100m ascent in about 1km.
The views at the top are pretty good!

Tip by

B

35.0 km

End point

Parking

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Way Types & Surfaces

Way Types

11.4 km

11.4 km

5.97 km

5.42 km

502 m

310 m

Surfaces

17.7 km

6.07 km

4.93 km

3.94 km

1.35 km

1.03 km

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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 (270 m)

Lowest point (90 m)

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Weather

Powered by Foreca

Sunday 10 May

14°C

2°C

25 %

Additional weather tips

Max wind speed: 20.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access the Win Green and Cranborne Droves Way Loop?

While specific parking details aren't provided, the loop is accessible from various points along its route. Many riders start near Sixpenny Handley or Berwick St John, which are good options for finding local parking. Always check for designated parking areas or local regulations before you go.

Is the Win Green and Cranborne Droves Way Loop dog-friendly?

Yes, dogs are generally welcome on this route. However, as the trail passes through farmland and areas with livestock, it's essential to keep your dog under close control, preferably on a leash, especially near grazing animals. Always follow the Countryside Code.

What is the best time of year to mountain bike this route?

The best time to ride this loop is during the drier months, from late spring to early autumn. During winter and after heavy rain, sections of the trail, particularly the ancient droving routes, can become significantly muddy, waterlogged, and feature deep ruts, making for a much more challenging ride.

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

No, there are no specific permits or entrance fees required to ride the Win Green and Cranborne Droves Way Loop. It is located within the Cranborne Chase and West Wiltshire Downs National Landscape, which is freely accessible to the public. However, always respect private land and follow local signage.

What kind of terrain can I expect on the trail?

The route features a diverse mix of terrain, including unpaved sections, gravel tracks, natural earth paths, and quiet country lanes. You'll ride along ancient droving routes like the Ox Drove and parts of old Roman roads. Be prepared for moderate gradients, some exhilarating descents, and potentially muddy, rutted sections, especially in wet conditions.

How challenging is the mountain biking on this loop?

This loop is generally considered a moderate mountain bike ride. It demands good fitness for the climbs and some advanced riding skills to navigate the more technical sections, particularly when dealing with mud, ruts, or steeper descents. It's not typically recommended for absolute beginners.

What are the main points of interest and views along the way?

You'll encounter several notable features and stunning views. Highlights include the historic Ox Drove Road (Cranborne Droves Way Trail), the iconic Win Green Summit with its distinctive beech trees and panoramic views over Blackmore Vale and Salisbury Plain, and White Sheet Hill. The route also passes through historic villages and ancient burial sites.

Does this route connect with other trails?

Yes, the Win Green and Cranborne Droves Way Loop incorporates sections of several other official trails. You'll find yourself on parts of the Cranborne Droves Way Trail, the Wessex Ridgeway Trail, The Hardy Way, and the Wiltshire Cycleway, among others. It also follows significant portions of the historic Ox Drove.

How long does it typically take to complete the loop?

On average, mountain bikers can expect to complete this 35 km (21.7 miles) loop in approximately 3 to 3.5 hours. This duration can vary depending on your fitness level, riding speed, and how often you stop to enjoy the views or navigate challenging sections.

Is this loop suitable for beginner mountain bikers or families?

Due to its moderate difficulty, varied terrain, and sections requiring advanced riding skills, this loop is generally not recommended for beginner mountain bikers or young families. Riders should have good fitness and some experience with off-road cycling, especially if conditions are wet.

How well is the trail marked?

The Cranborne Droves Way, which forms a significant part of this loop, is generally well-waymarked. Look out for the distinctive ram's head logo on green discs, which will help guide you along the ancient droving routes.

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