Take me home…

What does it matter that we take different road, so long as we reach the same goal?
Mohandas Gandhi


Roads may not sound exciting, but many of our roads have a fascinating history.

This page is in indexes: Island History Saint Helena Island Info RoadsIsland History, Island Place Saint Helena Island Info RoadsIsland Place, Island Structures Saint Helena Island Info RoadsIsland Structures, Island Detail Saint Helena Island Info RoadsIsland Detail

Roads Saint Helena Island Info

Below: Earliest HistoryNapoleon - good for our roadsAfter NapoleonMore exiles; more roadsFirst Motor CarLater 20th CenturyAsphalt MachineOur Newest RoadA Mystery Road or TrackRules for Road Users

The anchorage area in Jamestown was formerly known as ‘the Roads’.

Earliest History 

Below: Out of JamestownCountry RoadsState of these roads

Maps showing the development of our roads{a}:

Ken Denholm Map 1 Saint Helena Island Info Roads

Ken Denholm Map 2 Saint Helena Island Info Roads

Ken Denholm Map 3 Saint Helena Island Info Roads

Ken Denholm Map 4 Saint Helena Island Info Roads

Roads map 1933 Saint Helena Island Info

Out of Jamestown

Roads were not an immediate priority for the arriving colonists under Governor Dutton in 1659. They spent most of their time in Chapel Valley (now Jamestown), only going ‘up country’ (as it is still called today) for hunting and exploration.

As they became established they found there were parts of the island they needed to visit regularly, but getting out of the valley was not easy, given that it is surrounded by steep cliffs. Two routes became established:

Thornton 1702-7 Saint Helena Island Info Roads
Thornton, 1702-7

These were not originally roads as we know them today; they were merely well-trodden paths. Side Path was certainly in a relatively primitive state in 1677 when Halley visited; we know he had difficulty transporting his scientific equipment up it.

Shy Road/Ladder Hill Road seems to have been improved first. When the Plantation (now Plantation House but then literally a Plantation) was developed in 1673 it became necessary to haul goods to and from Jamestown, and the rope-assisted zig-zag path was not suitable. The new road, built early in the 18th Century and originally known as ‘Ladder Hill Path’ and later ‘Castle Path’, started at the base of the old path, behind where the Museum of St Helena is now, and took much broader sweeps up the hillside to make it navigable with carts. At the time there was no fort at Ladder Hill but there was a gibbet from which criminals were hanged, in plain view of the populus in Jamestown. In 1710 ladies and visitors were carried up the new road by ‘Blacks’ at a charge of 1/6d(£0.075) per trip - which went, of course, to the owners, not to the slaves themselves. The road was improved in 1733 by Governor Pyke, much to the anger of The East India Company in London who thought the money should have been spent improving the island’s defences.

A better road up Side Path came next, using some of the imported slave labour overseen by the island’s military, probably in the 1680s, possibly as a result of Halley’s complaints but also possibly not: two alarm guns were to be placed on the Ridge at Alarm Forest (at Alarm House) and an improved road may have been built to facilitate the transport of both the guns and the subsequent resources - troops; ammunition; powder, etc. Side Path was later extended as far as Hutt’s Gate and eventually in the late 18th Century all the way to Longwood.

1781 by Lafitte (extract) Saint Helena Island Info Roads
1781 by Lafitte (extract){b}


Lafitte’s map of 1781 (right) shows Side Path and both the old ‘Jacob’s Ladder’ path and the newer Shy Road/Ladder Hill Road.

The third route, up from the far Southern end of the valley, meeting Side Path at the top - now known as Constitution Hill - came much later.

Another project was the route up the eastern side of the valley to Munden’s Fort, overlooking the landing place (Wharf). Completed in 1713 this was a significant piece of engineering, requiring a strong stone retaining wall on the outer side, and an enormous amount of stone cutting around the high sea-facing cliffs of Munden’s Hill. Later extended beyond the fort, this became the only route into Rupert’s Valley until the present route, Field Road was built by Governor John Field in the 1960s. (The Munden’s route is still walkable as far as the fort but was lost to the sea above Romans Cove in September 1981{1}.) This route was eventually extended all the way round the island’s coastline as far as Banks Battery. You can see the route highlighted in the image below:

Aerial view showing Mundens Road Saint Helena Island Info Roads
Aerial view, showing Mundens Road

Country Roads

There were defences at Sandy Bay from the late 1690s (the defences are reported destroyed by Rollers in 1717) but there was no road and supplies were carried round the island by sea; a hazardous journey given that Sandy Bay is on the south-eastern side of the island so fully exposed to the trade winds and resultant seas. Governor Robert Jenkins built himself a house in Sandy Bay in 1741, but his only route there was an eight-mile cross-country horse ride so we assume he did not commute daily! However a rather precarious and winding road, extended from the route to the Plantation, followed two years later, and this remains today the road into Sandy Bay.

The cross-country route between Hutt’s Gate and the Plantation - incorporating what is now known as the ‘W Road’ (because of its shape) - was built around the same time as the Sandy Bay road, again based on an existing bridle path.

The route to Hutt’s Gate was extended to Longwood in or around 1787 when Governor Brooke identified the Longwood area as good for agriculture.

A route was proposed in the early 19th Century around the east (i.e. valley) side of High Knoll Fort, connecting upper Jamestown to Half Tree Hollow and the west of the island. But following consultation with the Directors of The East India Company the Records for 15th February 1833 report that it cannot be sanctioned in the present state of Indian finances. Construction was never started.

The state of these roads

In wet weather most of these roads were a quagmire and very greasy due to the presence of marl - a sort of stcky clay that covers a lot of the island’s surface. Sometimes they had a layer of broken stone placed over the worst sections, but this was the best that could be achieved with manual labour assisted perhaps with bullock-drawn carts. Fortunately the island has no significant rivers. The very few bridges that were required were invariably built of arched stonework, as was also used for the many miles of retaining walls. Rain is not uncommon on St Helena so for much of the year travelling must have been a nightmare.

Napoleon - good for our roads 

Napoleon Saint Helena Island Info Roads

Napoleon’s arrival on St Helena in 1815 changed everything. He could not, for security reasons, be housed in Jamestown (a decision with which the exile agreed - he valued his privacy), so Longwood House was chosen as his residence. His large staff had to be supplied, as did the many troops and defences set up to repel any attempt by his supporters to rescue him. This required a large number of new and improved roads, easily navigable in even the wettest weather. For example, a route had to be built down to Deadwood, where 500 soldiers were to be billeted.

In January 1816 it is recorded that Napoleon went riding in the direction of what is now Levelwood, but at that time there was no road so his journey was a rather adventurous cross-country ‘hack’. The accounts of his early time here say much about the state of the island’s ‘minor roads’ at the time, with several instances where the ox-cart intended to convey him and his party could not proceed due to the state of the road. On at least one occasion he was forced to get out and walk.

Fortunately (for our road network) no attempt was ever made to liberate Napoleon from his South Atlantic prison, so the 2,000-or so troops sent here to guard him had nothing much to do. Idleness leads to trouble, so they were put to work improving the island’s defences and its roads. By the time of Napoleon’s death in 1821 St Helena finally had the basis of a navigable road system, though much of the present network had not yet been developed.

Napoleon Street

Napoleon Street sign Saint Helena Island Info Roads

What is currently Napoleon Street (in Jamestown) is clearly so-named because it leads out of town towards Longwood, where Napoleon stayed during most of his exile here, and also leads to The Briars, the other place he resided while Longwood House was being made ready. But what was it called before Napoleon arrived? We understand that it was previously known as Cock Street, but we don’t know eiher why or exactly when it was renamed. It may have been when the roadway was levelled and macadamised in 1838.

After Napoleon 

Barnes Road 1911 Saint Helena Island Info Roads
Barnes Road, 1911
Jamestown pre-1882 (Ladder Hill Road extension) Saint Helena Island Info Roads
Jamestown pre-1882 (Ladder Hill Road extension)
Building China Lane? Saint Helena Island Info Roads
Building China Lane?

The financial effect of the reduction in troops following Napoleon’s death was keenly felt, and steamships took over from sailing ships depriving St Helena of its importance in world shipping. What better to do with an otherwise work-less population than for the Crown (which took over the island from The East India Company in 1834) to employ them constructing infrastructure? The New Ground and Guinea Grass areas were built up in the 1850s, complete with most of the current system of roads (Sapper Way was added later). The road to Levelwood via Woody Ridge was built at around the same time, and then extended on to join the Sandy Bay road in its current configuration.

In 1847 construction began on a route from upper Jamestown, via the Heart Shaped Waterfall to Francis Plain, which would become known as ‘Barnes Road’ after Major George Barnes who supervised the project. Sadly the resulting route was found too steep for donkeys to pull carts, and was all but abandoned soon after its completion. It is navigable today only as a footpath. (More about this road on our The Heart Shaped Waterfall page.)

Another route was the one linking the ‘W Road’ to the Sandy Bay road, around the base of the Peaks and up Stitch’s Hill.

Perhaps the most important new road built in the 19th Century was the extension of Ladder Hill Road down the western side of the valley to what is now China Lane (near the Hospital), completed in 1882. By avoiding the steep zig-zag of what is now called Shy Road (which today is an upwards-only connection, with a near-impossible sharp right turn at the top), traffic flow between Jamestown and the Ladder Hill Fort and west of the island was dramatically improved. The new portion of the route was originally named Phillips Road, but soon the route was known as Ladder Hill Road in its entirity and the old lower portion from lower Jamestown became known as Shy Road. Incidentally we think we know how Shy Road got its name…see our Place Names page.

None of the routes to the west, along the ridge from Casons to Head O’Wain, Blue Hill, Thompson’s and South West Point, existed as roads in the 19th Century, though there were settlements and/or military installations in all of these. All these routes were bridle-paths only at this time.

Longwood Gate Saint Helena Island Info Roads
Longwood Gate{c}

It is interesting to note that in the late 19th Century the opening and closing of gates along the road network was normal practice for road travel on the island. Most of the country roads passed over private land and very few were fenced so the various gates signified passing from one property to another and prevented the straying of livestock. Many of the old gateposts remain, usually as stout stone structures, and many placenames derive from these gates: Red Gate at Red Hill on the road to Plantation; White Gate at the entrance to Plantation grounds; Green Gate at the entrance to Plantation forests from Scotland; Sandy Bay Gate at the entrance to Stitches Hill road; Hutt’s Gate at the entrance to Hutts Gate district and giving access to Levelwood and Longwood roads; and Longwood Gate at the entrance to Longwood district.

We also think the image (right) shows the construction of China Lane (though it was probably also taken to record some event happening at St. John’s Church). Sadly we can’t date the image.

Someone was clever in 1885. The Secretary of State for The Colonies was advised that the roads on St Helena served no civilian purpose and were purely for the benefit of the military. As a result, responsibility for road maintenance was transferred to the War Department in London, which had much deeper pockets than the St Helena civilian administration! This plan was successful for only a while - in March 1909 a Road Tax was introduced at 3s/annum (£0.15).

More exiles; more roads 

The impetus for improving the ridge route to Blue Hill and beyond seems to have been the housing of about half the Boer Prisoners at Broad Bottom from 1900-1902. Indeed it is highly likely that the Boers themselves were employed in the road’s construction. The Zulu Poll Tax Prisoners (1907-1910) were also employd in road works, amongst other construction activities.

Boer Camp Broad Bottom Saint Helena Island Info Roads
Boer Camp, Broad Bottom

Zulu Prisoners working on Side Path 1907 Saint Helena Island Info Roads
Zulu Prisoners working on Side Path, 1907


The commencement of the Flax Industry in the early 1900s also created a demand for improved roads to transport the processed flax from the mills dotted around the island down to Jamestown for loading onto ships. Heavy Bullock drays required tougher roads, to which end a Road Tax was introduced on 1st March 1909 at 3s (£0.15). The Blue Hill road was upgraded all the way to Thompson’s Wood in the 1920s.

Sadly the road improvements were not uniform. In 1924 the streets of Jamestown were described as being in a bad state of repair and even worse than the country roads; the gravel streets frequently produced swirling dust that found its way into all the houses and buildings.

And then a technological arrival changed everything…

The First Motor Car 

The First Car Saint Helena Island Info Roads

In 1919 motorised transport was prohibited on St Helena by Ordinance. This was revoked in 1927 and the first car arrived two years later. Early cars struggled with roads quite passable by ox-cart, so a programme of road improvements soon began. A motor roller and stone crusher arrived in May 1928 and by November the same year 60 miles of island road were declared ready for the expected influx of motor cars. By the end of 1930 there were 14 cars and 5 lorries enjoying these new roads.

Later 20th Century 

Not one of our better roads Saint Helena Island Info
Not one of our better roads
Under repair Saint Helena Island Info Roads
Under repair…

The road into The Briars was opened in 1937. Sealing of roads began after World War 2 and the same process is used today. This is not Tarmac, as is used elsewhere in the world. Chipped stone is pressed into Colas - a bitumen substance - with a roller to form a surface. Theoretically the excess stone is swept up, but in practice it is usually left in drifts on the road, presumably in the hope that vehicles will press it into the road; a mostly failed hope and much of the loose stone ends up blocking the roadside drains. The road to Blue Hill was upgraded in 1959.

Following the closure of the Flax Mills in 1966 the resulting unemployed were deployed on Government-funded projects, including improved access to Levelwood and Sandy Bay. Field Road, the current route into Rupert’s Valley from the junction of Constitution Hill and Side Path, was built by Governor John Field, opening in May 1968; fortunately so because the older route via Munden’s Fort was closed beyond the fort in 1981 due to undercutting by the sea above Romans Cove{1}. And the creation of the island’s Diplomatic Wireless Station in 1965 led to upgrading of the road from Longwood Gate past Piccolo Hill (where the DWS Staff were housed) down into Bottom Woods.

In 1982 a new road was built by the Royal Engineers from New Ground road to join the Red Hill road near Model Cottage. This very useful connecting road was accordingly named Sapper’s Way (now shortened to ‘Sapper Way’). By this time the last horses on the island had died so apart from a number of donkeys used almost exclusively for fodder transport our roads were given over exclusively to motor vehicles.

The Mini-Roundabout outside the Canister in Jamestown, the island’s first, came into operation on 2nd February 1987 (the second and, so far only other one, in Scotland, came in in July 1990. The one-way system around the flats opposite St. John’s Church was introduced in the 1990s. Ladder Hill Road (described in The ‘Blue Book’ for 1970/3 as this inevitably difficult and tortuous road) was widened in 2000 and the 15mph speed limit removed (it is now 20mph like the rest of Jamestown).

The Asphalt Machine 

Scrapped Asphalt Plant Saint Helena Island Info Roads
Scrapped Asphalt Plant

As incomes began to rise after the Millennium (and also as in 2004 Bank of St Helena began offering car loans) people started buying and importing newer and more modern vehicles. Performance cars began to appear and this led to rising criticism of the poor state of the island’s roads. The ‘spread and (hopefully) stick’ method of road maintenance was particularly unpopular due to the damage done to vehicles by the loose stones. Responding to this criticism, in 2011 Government of St Helena purchased an Asphalt Plant, intended to manufacture Asphalt on the spot so that our roads could be given a stronger, more even surface without the drifts of loose stones. Sadly, when the machine arrived it was discovered that significant parts were missing and those parts that were present could not be operated safely. After many failed attempts to obtain the missing parts the machine had to be scrapped, at great expense.

One of our major roads Side Path in October 2018 Saint Helena Island Info
One of our major roads, Side Path, in October 2018{d}

Our Newest Road 

For the construction of St Helena Airport it was necessary to build a whole new route to transport the materials and equipment for construction from Rupert’s to Prosperous Bay Plain. The route chosen climbed the eastern side of Ruperts Vally, proceeding on to Deadwood, then circiting Longwood and Bottom Woods down to the Airport. Initially just a packed-earth track, it was planned that when the ‘Haul Road’ was no longer needed it would be properly surfaced and added to our road network. The entire length has been finished and the section from the Bottom Woods junction is now the official road to the airport. At the time of writing the part from Rupert’s to Bottom Woods has not been opened to the public.

Incidentally, the Haul Road is Asphalt-surfaced. Basil Read had Asphalt making equipment available for surfacing the Airport runway…

The haul road route Saint Helena Island Info Roads
The haul road route

Construction Traffic Saint Helena Island Info Roads
Construction Traffic

The completed road Saint Helena Island Info Roads
The completed road


A Mystery Road or Track 

We came across this old French postcard of St Helena. It isn’t dated but we assume to to be middle- to late-19th Century (before the extension of Ladder Hill Road down to China Lane, which was completed in 1882). It shows (left) a track or road leading from somewhere behind the Baptist Church snaking up the hillside to meet the Shy Road/Upper Ladder Hill Road junction. We can find no mention of this route in the Records.

We can’t tell from the photograph if this was simply a footpath or whether it could be used by vehicles. From the gradient it is likely it was for pedestrians only, though it looks wide enough for a narrow cart. It was probably made to allow the soldiers in The Barracks (the buildings in the centre bottom of the image) to get more quickly to and from Ladder Hill Fort without having to travel further down into the town to ascend Shy Road.

Can you tell us more about this route?

The mystery road or track Saint Helena Island Info Roads

Rules for Road Users 

Summarised from our Driving in St Helena page:

Wrecked car Saint Helena Island Info Roads
Try not to crash

Rain can still be a problem Saint Helena Island Info Roads
Rain can still be a problem

Closing Humour Saint Helena Island Info Roads

Laugh at funny Roads humour LOL Saint Helena Island Info


{a} Ken Denholm, from ‘A History of Road Development’. Last map from The ‘Blue Book’ for 1933.{b} UK National Archives MPH 1/251{3}{4}{c} Derek Richards{d} Andrew Turner


{1} From the St Helena News Review, 4th September 1981: The Highway Authority wishes to inform the public that the road leading from Mundens Point to Ruperts Bay will be closed with effect from today. Part of that section lies over Romans Cove and has been seriously undercut by the action of the sea. The Authority therefore agreed that people using that section would be in danger and decided to close it.{2} We are told that the highest speed actually obtained on a St Helena road is 120mph, but obviously we have not verified that - and neither have the Police.{3} Reproduced for educational non-commercial use only; all copyrights are acknowledged.{4} Not to be confused with the St Helena Archives.

Take Me Anywhere But Here!

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