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South West England
Dorset
East Dorset

Sixpenny Handley And Pentridge

The best family-friendly hikes and walks around Sixpenny Handley And Pentridge

4.7

(494)

2,777

hikers

199

hikes

Family friendly hiking trails around Sixpenny Handley And Pentridge traverse a landscape characterized by rolling hills, ancient woodlands, and expansive chalk downlands. Situated within the Cranborne Chase National Landscape, the region offers diverse terrain with gentle ascents and open vistas. Hikers can explore features like Pentridge Hill and various ancient earthworks, providing a blend of natural beauty and historical interest. The area's chalk downlands contribute to its unique flora and fauna, making it suitable for varied outdoor exploration.

Best family…

Last updated: July 1, 2026

4.9

(12)

45

hikers

#1.

Win Green Summit – View of Ferne House loop from Farnham

13.3km

03:42

250m

250m

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

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Moderate

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard
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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
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Tips from the Community

Rona 🐶 + John 🤦🏼‍♂️
March 29, 2025, Gate to Ashdown House Public Footpath

This unlocked gate facilitates access to a little-used public footpath across the Ashdown House property. It is NOT signed as a public path but it definitely is.

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Luke
October 24, 2024, Win Green Summit

One of the most beautiful places in the south of England 🏴󠁧󠁢󠁥󠁮󠁧󠁿 and amazing views of Wiltshire and Dorset 🤩

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I really enjoyed cycling the Wiltshire Droves, although in May is was very very wet and muddy and needed to walk in places. highly recommend it

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Look down to see the beautiful Ferne House and grounds.

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51m
October 15, 2023, Win Green Summit

Win Green at 277 m is the highest point on Cranbourne Chase. The tree topped summit also has a Bronze Age hill barrow, topography stone and trig point. Lots of great running loops from here as well as easy parking close by.

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More gravel path than grassy. But some nice shaded parts. Bullocks at end.

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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 the cows towards Salisbury and then onward to the ports at Southampton. The section that is rideable today passes an old ale house, dew ponds and grain storage sheds. The surface is easily rideable on a mountain bike but does get a bit muddy in the winter. Great views all year though! This is part of the Cranborne Droves Way Trail, a 27km route that links the Sarsen Way at Salisbury with the Wessex Ridgeway Trail at Win Green.

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51m
October 19, 2022, Win Green Summit

Win Green hill at 277m is the highest point on Cranborne Chase. The trig point affords panoramic views apart from the bit blocked by the little clump of trees on the summit. The beech trees are growing on a Bronze Age bowl barrow. It's managed by the National Trust and is often busy because it's close to a car park. Still very nice though!

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Frequently Asked Questions

How many family-friendly hiking trails are available around Sixpenny Handley and Pentridge?

There are over 200 hiking routes in the Sixpenny Handley and Pentridge area, with 60 of them specifically rated as easy, making them ideal for families. Many of these trails traverse the beautiful Cranborne Chase National Landscape, offering diverse scenery for all ages.

What kind of terrain can we expect on family hikes in this region?

The region is characterized by rolling hills, ancient woodlands, and expansive chalk downlands. You'll find paths through open vistas, gentle ascents, and sometimes historical earthworks. Trails are generally well-maintained, but some can be uneven, especially in wooded areas or after rain.

Are there any specific landmarks or natural features to look out for on family walks?

Absolutely! The area is rich in history and natural beauty. You can explore ancient earthworks like Bokerley Dyke, a significant Roman-British defensive ditch. For panoramic views, consider a walk towards Win Green Summit, the highest point in Cranborne Chase, where on a clear day you might even see the Isle of Wight. Other notable features include the unique chalk grassland of Martin Down National Nature Reserve and ancient woodlands like Chase Woods.

Are there any circular routes suitable for families?

Yes, many of the family-friendly trails are circular, allowing you to start and end at the same point. For example, the route "Win Green Summit – View of Ferne House loop from Farnham" offers a moderate circular hike with rewarding views. The area's network of paths often allows for varied loop options.

What is the best time of year to go hiking with family in Sixpenny Handley and Pentridge?

Spring and summer are particularly lovely, with wildflowers blooming across the chalk downlands and the woodlands in full leaf. Autumn offers beautiful fall colors. While winter walks can be crisp and clear, some paths might be muddy, so appropriate footwear is always recommended regardless of the season.

Are there any easy, shorter walks suitable for young children or pushchairs?

While many routes are moderate, there are easier sections and shorter loops that can be adapted for young children. For pushchair-friendly options, look for trails that follow wider, flatter paths or bridleways, as some of the more natural woodland or chalk downland trails can be uneven. It's always best to check the specific route details for terrain suitability.

Where can we find parking for family hikes in the area?

Parking is often available in or near the villages of Sixpenny Handley and Pentridge, as well as at designated car parks for popular trailheads within the Cranborne Chase National Landscape. Many routes, such as "Church Farm Campsite loop from Sixpenny Handley", start from accessible village locations. Always check local signage for parking restrictions or fees.

What do other hikers enjoy most about the family-friendly trails here?

The area is highly rated by the komoot community, with an average score of 4.66 stars. Reviewers often praise the peaceful, unspoiled countryside, the sense of history along ancient earthworks like Bokerley Ditch, and the stunning panoramic views from points like Win Green Summit. The variety of landscapes, from open downland to ancient woodlands, is also frequently highlighted.

Are there options for refreshments or family-friendly pubs near the hiking trails?

Yes, the villages of Sixpenny Handley and Pentridge, as well as nearby hamlets, offer options for refreshments. You can often find traditional pubs that welcome families, and some may have outdoor seating. It's a good idea to check opening times in advance, especially if you're planning a hike that ends later in the day.

Can we bring our dog on these family hikes?

Many trails in the Sixpenny Handley and Pentridge area are dog-friendly, allowing your furry family members to join the adventure. However, please be mindful of livestock, especially on chalk downlands, and keep dogs on a lead where indicated or when near farm animals. Always follow the Countryside Code and clean up after your dog.

Are there any less crowded or 'hidden gem' family walks in the region?

While popular spots like Win Green Summit attract visitors, the extensive network of trails within Cranborne Chase means it's often possible to find quieter paths. Exploring the ancient woodlands or lesser-known sections of the chalk downlands, such as those found on routes like "Tollard Royal Village Pond loop from Sixpenny Handley", can offer a more secluded experience. Early mornings or weekdays are generally less busy.

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