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Ashdown Forest and Five Hundred Acre Wood loop — High Weald

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Hiking trails & Routes

Ashdown Forest and Five Hundred Acre Wood loop — High Weald

Moderate

4.7

(84)

264

hikers

Ashdown Forest and Five Hundred Acre Wood loop — High Weald

04:29

16.4km

260m

Hiking

This moderate hike through Ashdown Forest and Five Hundred Acre Wood offers a diverse landscape, transitioning from open heathland with expansive views to dense, ancient woodland. You will traverse areas of heather, gorse, and pine, then enter a forest of beech, silver birch, and sweet chestnut trees. The 10.2-mile (16.4 km) loop involves a steady climb of 848 feet (259 metres) to the forest heights, taking about 4 hours and 28 minutes to complete.

While generally accessible, some sections require sure-footedness, and the initial parts in the Low Weald can be muddy due to clay soils. As you ascend into Ashdown Forest, the sandstone terrain typically provides drier walking conditions. This route is suitable for most hikers with good fitness, offering a rewarding experience through varied terrain and scenery.

The trail is famously known as the inspiration for A.A. Milne's Winnie-the-Pooh stories, with many real-life locations mirroring those in the books. You can discover the Five Hundred Acre Wood, visit Pooh Bridge to play Poohsticks, and imagine characters like Eeyore and Roo in their respective places. This connection makes the hike particularly popular with families and children, adding a touch of literary magic to your outdoor adventure.

Last updated: April 23, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

High Weald AONB

Waypoints

Start point

Parking

Get Directions

2.18 km

Gills Lap Clump (The Enchanted Place)

Highlight • Viewpoint

This clearing surrounded by fir trees appears in the Winnie the Pooh book as "Galleons Lap" or "the Enchanted Place." Next to it, there is also a trig point.

Tip by

2.37 km

Roo's Sandpit

Highlight • Historical Site

This site might sound familiar to you, as it's the sandpit where Roo used to play peacefully in the Winnie the Pooh books. It was a former quarry.

Tip by

2.47 km

A. A. Milne and E. H. Shepard Memorial Viewpoint

Highlight • Monument

Atop this glorious viewpoint, you find a memorial to A. A. Milne, the English author best known as the creator of Winnie-the-Pooh, and his collaborator, E. H. Shepard. On the plaque, there is a quote from The House at Pooh Corner, which reads: “And by and by they came to an enchanted place on the very top of the Forest called Galleons Lap.” Around this area you find lots of places featured in Winnie-the-Pooh.

Tip by

4.84 km

Owl's House (Winnie-the-Pooh)

Highlight • Viewpoint

Be sure to look up into the trees to spot Owl's house. This is a perfect trail for children as they love looking out for the characters' homes from AA Milne's 'Winnie the Pooh' books.

Tip by

5.15 km

Pooh Bridge

Highlight • Historical Site

Fans of AA Milne's 'Winnie the Pooh' books will love visiting poohsticks bridge. Locals say this is the location where AA Milne first played poohsticks with his son, Christopher.

Although this is not the original, as the first, called Posingford Bridge and built in 1907, fell into disrepair as so many people visited and walked on it. This bridge was erected in 1999 in the same style and was built with help from a grant from Disney.

Make sure to carry some sticks with you to the bridge so you aren't disappointed!

Tip by

5.22 km

Winnie-the-Pooh's House (Mr. Sanders)

Highlight • Structure

The smell of hunny will lead you straight to Winnie the Pooh's house. Complete with the Mr SAИDERZ sign, this is a great place for children and Winnie the Pooh fans to look out for.

Tip by

7.77 km

St Mary's Church, Hartfield

Highlight • Historical Site

Distinctive double-pitched steeple.
There are some really old houses along Church Street (High Weald Landscape Trail), including one with an unusual projecting first floor.

Tip by

12.8 km

Five Hundred Acre Wood

Highlight • Forest

Five Hundred Acre Wood is famously the inspiration behind Hundred Acre Wood, the setting for AA Milne's Winnie the Pooh stories. Unlike the rest of Ashdown Forest, which is now heathland, Five Hundred Acre Wood is still a forest, having been replanted and enclosed 300 years ago to protect it from grazing. The trails here make for an enchanting adventure in any season.

Tip by

14.9 km

Greenwood Gate Clump

Highlight • Viewpoint

Along with Crowborough Beacon, which is just slightly higher, Greenwood Gate Clump is one of the highest points in the High Weald AONB at 732 feet (223 m). It is the highest point on the Wealdway long-distance trail between Gravesend and Eastbourne. From its surroundings you can take in an extensive panorama, with both chalk escarpments of the North and South Downs, as well as the rural pastures of East Sussex and Kent.

Tip by

16.4 km

End point

Parking

Way Types & Surfaces

Way Types

5.24 km

3.98 km

3.97 km

2.19 km

965 m

Surfaces

10.1 km

4.59 km

1.15 km

546 m

< 100 m

Elevation

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

Highest point (220 m)

Lowest point (50 m)

Weather

Thursday 7 May

18°C

6°C

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This route was planned by komoot.

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Trail Reviews

Peter Langford

September 7, 2024, Hike to Winnie the Pooh House

This is a great walk, lots of scenic woods, good views and Winnie the Pooh stuff that is obviously still a big draw 🐻 🍯 Started it from Hartfield where there is a lovely pub called the Bear. A fair bit of climbing but not too strenuous and navigating was dead easy thanks to the app and also the debut of my arm phone holder 🙂👍 even a big downpour didn't dampen our spirits one bit 😁

Ashdown Forest and Five Hundred Acre Wood loop — High Weald

Gills Lap Clump (The Enchanted Place)

Roo's Sandpit

A. A. Milne and E. H. Shepard Memorial Viewpoint

Owl's House (Winnie-the-Pooh)

Pooh Bridge

Winnie-the-Pooh's House (Mr. Sanders)

St Mary's Church, Hartfield

Five Hundred Acre Wood

Greenwood Gate Clump

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Trail Reviews

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