
A large forest of gumwood trees once grew here, known as the Great Wood. It was cut down, presumably for firewood, leaving just tree stumps behind, which led to the name, Deadwood Plain. The fenced off paddocks are used for cattle grazing.
THE EASY-PEASY HIKE ON ST HELENA | Darrin Henry
As outdoor adventure on St Helena goes, the Flagstaff post box walk is hardly expedition grade stuff; mountain boots or sustenance backpacks not necessary for what is essentially a scenic trail that begins on Deadwood Plain. At the same time, this should be on everyone’s list of outdoor activities if they only have a week on St Helena.
It’s one of the guided photography walks we do, on its own and as a bolt-on to other routes.
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Foxy’s Garage, the starting point of the Flagstaff Post Box walk on Deadwood Plain. Keep right, through the vehicles and the gate. The peak of Flagstaff quite clearly straight ahead across the Plain.
The top three reasons you should do this walk:
- It’s easy – as Post Box walks go. It’s been rated 2/10 in the SNCG walks book
- It’s quick – achievable in under an hour if time is short (quicker with a 4×4)
- It’s spectacular – the views are simply brilliant! Take a camera.
There’s a bonus reason and one of my favourite things about the Flagstaff post box walk, but that comes later!
Starting At Foxy’s Garage
Today, with the sky beautifully clear at 3pm, we made a last minute decision to get outdoors and hike Flagstaff.
Foxy’s Garage on Deadwood Plain is the starting point. You won’t find a big sign declaring ‘Foxy’s Garage’ so if you’re new to St Helena look for the gate next to the ‘waiting room’ of broken vehicles.
There’s a dirt track cut through the Plain which we usually drive across, but today, for authenticity’s sake (for the blog), we’ve parked at the garage and will be walking the entire route!

Starting out across Deadwood Plain on the Flagstaff Post Box walk. The information boards shown here contain very interesting snippets about the walk, the wirebirds and Deadwood Plain.

More of the flora seen on the Flagstaff Post Box walk. Everlasting flowers (left) and the tough Lantana bush (right).

Deadwood Plain was home to around 6,000 Boer prisoners from 1900-1902. Very hard to imagine the scene today. In the distance we can see houses in the community of Longwood – the Deadwood and Longwood districts are squeezed up against each other.
Left: A cactus plant flowering on the Plain.

The strong, reliable south-east trade winds sweep across Deadwood Plain, making it an ideal location for the island’s wind farm, if a little unsightly on such a beautiful expanse of landscape. The first turbines were installed in 1999. Today there are twelve of the electricity generators rising up on the Plain.
Deadwood Cattle
The deep blue above us is gorgeous and at 4.15pm the grass and rolling hills away to our right are bathed in warm afternoon light. Mouth-watering conditions for photographers.
This first part of the hike, following the Land Rover track, is easy-peasy. It’s level and straight. In fact the only hazard (if you can call it that) is the danger of stepping into a cow pat. Yes, there are cattle. A healthy looking herd combined from local farming syndicates roam freely all over Deadwood Plain, moving between open paddocks marked with barbed wire fences.

Cattle grazing, or lazing actually, on Deadwood Plain.
Home Of The Boer War Prisoners
There are no clues that the empty rolling Plain before us was once home to 6,000 prisoners of war. A simple sign post alongside the track, “Boer Prisoner of War Camp Site. 1900-1902” is the only reminder of the tented community that lived here between 1900-1902. In St Helena summer weather, a tent on Deadwood Plain sounds like fun, but winter weather on St Helena is notoriously miserable in comparison. This part of the island especially receives its fair share of fog, wind and rain, so I have a lot of sympathy for the men huddled here at the start of the last century.
St Helena Wirebird Habitat
Today Deadwood Plain is one of the major habitats for St Helena’s endemic Wirebird. We spot a few running away from the track we’re on, a typical tactic to divert our attention from the nests, which are made on grass and quite difficult to spot.
Ahead in the distance the sweeping curve of Flagstaff itself, rises proudly at the end of Deadwood Plain. About halfway along are 12 wind turbines of which 10 are spinning.
It takes 10 minutes to reach the wind turbines and find ourselves walking between the columns – a rapid swoosh, swoosh, swoosh… the sound of green energy!

Deadwood Plain is one of the three core nesting sites for St Helena’s endemic wirebird. A member of the plover family of birds, the wirebird is listed as ‘Critically Endangered’ by the IUCN. Predation from feral cats and rats are a constant threat to the population of wirebirds which is probably how this little one met its end. These remains were on the track.

When the light is good everything is a photographic distraction for us, even the wind farm!
Clockwise from top: The concrete generator room is a good half way marker for the walk; these blades were actually spinning quite fast; two generator heads on the ground for maintenance; Sharon viewing one of the blades gives a good sense of how scale for the size of the blades.

Continuing toward Flagstaff. Behind us the cloud covered central peaks. Off to the left the houses in Longwood can be seen.

Sheep farmer, Mark Coleman, feeding his flock up on the slopes of Flagstaff. In the far distance St Helena’s new aiport and runway is visible on Prosperous Bay Plain.

Dinner time for these sheep. The dark shadow of Flagstaff looms in the distance for us, as clouds now beginning to form in the late afternoon.
The Yellow Nuisance
After the wind farm the track begins the gentle ascent. It’s tempting to keep stopping to take photographs as the light is perfect and the views are amazing, but we push on, conscious the late afternoon temperature drop is already dragging in some cloud.
The fields and paddocks now give way to a few smaller sheep pens. Up here there are patches of the invasive furze bushes. Furze have small, attractive yellow flowers, but make no mistake, for land owners this plant is a real nuisance with its vicious spikes. In fact, only a few years ago this hillside was covered in furze, but a St Helena National Trust project to improve the Wirebird habitat has done an excellent job of clearing the invasive pest.

This is a picture we took in September 2009 when the furze bushes covered the upper slopes of Flagstaff. Very pretty when they flowered but otherwise not nice. The effort by the St Helena National Trust to remove the furze has been impressive with the reclaimed land now used for sheep farming, as we saw earlier.
Meeting Mark
Up ahead we spot a Land Rover and nearby is Mark Coleman, a sheep farmer who leases these upper fields for his 30 strong flock. We stop to chat for a little while and catch our breath. Mark is feeding the sheep with freshly cut grass from another part of the island – the grass up here isn’t as nice.
On we go. It’s taken us about 35 minutes but we’re now at the final stage; the bottom of the tree line that covers the summit of Flagstaff.

The road nearer the top of the Flagstaff Post Box walk is lined by the vicious furze bushes. Furze on St Helena are one of the most awkward invasive plants to remove because of their sharp spikes.

This field on the upper slopes of Flagstaff, St Helena, was overrun with furze bushes just a few years ago. It is now reclaimed and useful farming land. The rounded shaped peak to the right in the far distance is Great Stone Top.

Looking back at St Helena from inside the tree line on Flagstaff. The houses we can see are in Longwood.
Flagstaff Post Box Walk – The Top of the Hill
This last part of the hike, through the trees, is the steepest, but it’s mercifully short. Five minutes of steady climbing and we’ve reached the top. Through the trees to the far side; the seaward side and, BAM! This is what Flagstaff is all about, the incredible views!
We’re basically now at the top of a 700m cliff with the vast Atlantic panorama curving all around us.
Flagstaff Bay is way below with the wisps of white surf lining the coastline. The large, dark hulk of Longwood Barn is off to the right (a much more difficult post box walk) and further to the right still we can just make out the end of the new airport runway. The distinctive shape of Turks Cap lies lower down in the valley.

Flagstaff Post Box walk – Sharon writing in the visitors’ book at the top. The pipe on the left is the actual ‘Post Box’ where you will find the book and stamp. Most of the post boxes on St Helena have a similar setup.

The end of the runway at the St Helena airport is just visible from the top of Flagstaff. The hill in the middle caught in the sunlight is Horse Point.

From the top of Flagstaff, St Helena, looking across to the Longwood Barn. The knobbly shape of Turks Cap is visible off to the right.

From the top of Flagstaff, this is the view down to Sugar Loaf. Banks Battery is down in the ‘V’ of the valley to the left, running all the way along the coast under Sugar Loaf. This is one of our pictures from 2005. The view is unchanged 11 years later!

The sun was sinking low by the time we reached the top of Flagstaff, but we had used a lot of time up taking photographs on the way up. Behind us in this picture is The Longwood Barn, a much more difficult Post Box walk for another day.

From the top of Flagstaff, pausing to enjoy the view across St Helena before making the journey back to the car. The clear blue skies from a few hours ago are well and truly gone!
Bonus Time
In the opposite direction, off to our left is Sugar Loaf, an important waypoint landmark used by sailors. The historic fortifications of Banks Battery are out of sight below Sugar Loaf, where we once hiked to do a photoshoot with model, Emma-Jay. Ruperts Valley and Jamestown are both hidden in the next two valleys along but above them we can see sprawling district of Half Tree Hollow.
Sharon records our trip in the post box visitors’ book and now it’s time to head back. And this is where the bonus for hiking to Flagstaff kicks in – the return journey is all downhill!

Flagstaff Post Box walk is one of the easiest to do on St Helena and one we’ve done many times over the years. This is us at the top in 2009 with our ‘little man,’ Jasper, who used to lead us on every walk we did on St Helena. Sadly, no longer with us, but a very happy memory.
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Disclaimer: The information in this article is not intended as to validate the safety or otherwise of the walk route. Trails on St Helena are subject to change depending on weather conditions, plant growth and natural erosion. Walkers unfamiliar with the walks on St Helena should seek the assistance of a competent local guide.
Lovely to see these photographs,my family farmed Longwood Farm when the Boer prisoners were there.(Deason brothers)
Fascinating stuff, thank you!
I came across your site whilst researching my great great grandfather Augustus Kolbe Enslin who was a POW on St Helena during the Boer War. He was captured along with about 4000 other Boers at Paardeberg when Gen. Cronje surrendered. I inherited his very moving letters to his wife as well as some postcards and a photo of him on the island.
I actually found a photo of him along with his ‘house’ mates on a site called geheugenvannederland.nl . There are plenty of photos of Boer prisoners at Deadwood camp there!
It was great to see what the place looks like now, as back then it was just a dust bowl!
Wow thanks for sharing that lovely piece of history – love that the letters have been kept after all this time. Didn’t realise so many photos existed of the Boers on St Helena until we saw that website – couldn’t read the captions though, we’ll have to learn Dutch!
Thanks, Darren and Sharon. This brings back great memories of doing the walk after the Fair on Longwood Common in the Bicentennary Week last October. By the time we reached the summit, the weather had turned and it was cold and windy. Take a jacket even if it is sunny back in Jamestown!
Bronwyn, that’s a good point about the weather and taking a jacket. We actually had very light-weight rain jackets in the bag, always take them just in case. Glad you enjoyed the post, thanks for the feedback. Cheers 🙂
Yeah, we had those cheap ponchos in our packs and they did the job, even if the wind billowed under them and we nearly took flight over The Barn!