Sixpenny Handley And Pentridge
Sixpenny Handley And Pentridge
4.6
(43)
1,916
riders
8
rides
No traffic road cycling routes around Sixpenny Handley And Pentridge traverse a landscape characterized by gently rolling chalk uplands, expansive downland, and valleys within the Cranborne Chase Area of Outstanding Natural Beauty. The region features prominent hills like Pentridge Hill, offering panoramic views, and Win Green, the highest point, providing extensive vistas. Road cyclists will find routes that navigate quiet lanes through this rural setting, often passing woodlands and historical earthworks. The terrain includes varied surfaces suitable for road bikes, with options for both moderate climbs and smooth descents.
Last updated: May 4, 2026
3.0
(2)
41
riders
50.9km
02:27
530m
530m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
22
riders
55.6km
02:39
440m
450m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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9
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
28.7km
01:23
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Sixpenny Handley And Pentridge
On the corner of the village are these beautiful Roman style Pillars, opposite what looks like an old Roman road
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This is a significant historical landmark. It's the surviving part of a much grander house designed by the renowned architect John Vanbrugh (who also designed Blenheim Palace and Castle Howard) and built between 1717 and 1738. The larger part of the house was unfortunately demolished in 1782 due to a fall in family fortunes. The grounds still show evidence of the original gardens designed by Charles Bridgeman.
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A beautiful ancient bridge lovely views in all seasons x
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A place for a rest if you need it
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Beautiful Dorset countryside - rolling hills - nothing too steep
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There are toilets here - usually open during the day
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There are 8 dedicated no traffic road cycling routes in the Sixpenny Handley And Pentridge area, ranging from easy to moderate difficulty. This includes 3 easy routes and 5 moderate routes, ensuring options for various fitness levels.
The area is highly rated by the komoot community, with an average score of 4.6 stars from 44 ratings. Cyclists frequently praise the quiet, scenic roads, the rolling chalk uplands, and the sense of tranquility offered by the Cranborne Chase Area of Outstanding Natural Beauty.
Yes, there are several easy routes perfect for beginners. For instance, the Smooth Descent to Sixpenny – Chalk Downland Descent loop from Sixpenny Handley is an easy 25.8 km ride with manageable elevation. Another great option is the Compton Abbas Airfield – View of Eastbury House loop from Cashmoor, which covers 28.7 km with gentle climbs.
The routes primarily traverse gently rolling chalk uplands, valleys, and expansive downland. While mostly paved, some routes may include sections that are suitable for road bikes that can handle varied surfaces, or hybrid bikes, especially if you venture onto quieter lanes that might have some gravel. The region is known for its beautiful views and descents.
The area is rich in history. You can encounter ancient sites like the long defensive ditch of Bokerley Dyke. Other notable points include Win Green Summit, the highest point in Cranborne Chase, offering panoramic views, and the intriguing The Miz Maze. The Roman road of Ackling Dyke is also a significant historical path that can be integrated into cycling routes.
While the guide focuses on no traffic routes, many of the moderate routes offer good challenges. For example, the Wimborne St Giles Pond – Ashmore Village and Pond loop from Sixpenny Handley is a longer 69.7 km route with over 800m of elevation gain. The region also features climbs like Zig Zag Hill near Win Green, known for its challenging ascent and views.
The area offers several options for refreshment stops. You can find local pubs such as The Penny Tap in Sixpenny Handley, The Museum Inn in Farnham, The Drovers at Gussage All Saints, and The Bull at Wimborne St Giles. These are often conveniently located in picturesque villages along or near popular cycling paths.
The best time for road cycling in this region is generally from spring through autumn, when the weather is milder and the landscapes are vibrant. Clear days offer breathtaking vistas from elevated points like Win Green. While winter cycling is possible, be prepared for potentially colder, wetter conditions and shorter daylight hours.
Yes, many of the routes are designed as loops, allowing you to start and end in the same location. For instance, the Smooth Descent to Sixpenny – Chalk Downland Descent loop from Cashmoor is a popular circular option. The The Cliff Ascent – Wimborne St Giles Pond loop from Sixpenny Handley also offers a great circular experience.
While Sixpenny Handley and Pentridge are rural villages, public transport options might be limited. It's advisable to check local bus services for connections to nearby towns like Blandford Forum or Salisbury, from which you might be able to cycle to the starting points of the routes. Parking is generally available in the villages for those arriving by car.
Absolutely. The region is known for its stunning vistas. Win Green Summit offers panoramic views across Blackmore Vale and Salisbury Plain, and on clear days, you can even see the Isle of Wight. Other excellent viewpoints include Melbury Beacon, Pentbury Knoll (Pentridge Hill Summit), and View from Charlton Down, all providing breathtaking scenery of the rolling chalk uplands.


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