War and Peace in Castletown

Start/Finish: Portland Castle

Distance: Approx 1.5 miles

Terrain: Flat

Things to do: Portland Castle, Sailing Academy, Leisure Centre, D-Day Museum


Originally the location for fishermen to launch their boats, Castletown grew in the  shadow of Portland Castle which gave it its name. Castletown later developed during the 19th-Century with the construction of Portland Harbour’s breakwaters, and the establishment of the naval base.  The Royal Navy left in 1995 and since then the sailing academy has been established  and hosted the 2012 Olympic sailing events.

The Walk

There is no better place to start the walk than at the castle that gave this village its name.

Portland Castle www.english-heritage.org.uk


Entrance to Portland Castle

In 1539 King Henry VIII ordered the building of Portland Castle (and Sandsfoot Castle in Weymouth) to protect his new Royal Navy that were anchored in Portland Roads from attack from the French or Spanish.

The castle experienced its only fighting action during the English Civil War 1642-1649. As a Royal Manor, Portland was a Royalist stronghold. Nearby Weymouth  backed the Parliamentarians. A succession of battles saw Portland Castle captured and recaptured several times. Portland surrounded in 1646.

The Captain’s House is a large detached house, adjoining Portland Castle. It was built between 1816 and 1835 by the Royal Navy.

Located around 23 meters south of the entrance to The Captain’s House is a War Department/Admiralty boundary marker. Dating from 1870, it is one of many markers of its kind to be found on Portland. See how many you spot on this walk

Once you have finished at the castle turn right onto Mulbury Road and follow the blue sign to Osprey Quay and National Sailing Academy.

1959 saw the formation of the Royal Naval Helicopter Station, which was built on the site the old Mere (tidal lagoon), where centuries of shepherds had come to dip their sheep. The huge RNAS helicopter base closed in 1999 and here now you will see the HM Coastguard helicopter

Carry on walking till you reach  a rather large log – a warning to what can be found out at sea.  Directly in front is a viewing platform which is an excellent spot to see the breakwaters and Portland Harbour.

Portland Harbour

Spring day at Portland Harbour

This is the largest artificial harbour in the UK. Construction of  the breakwaters began in 1849 when Prince Albert laid the first stone. Engineers and skilled craftsmen  came from all parts of the country, while thousands of convicts who had been sentenced to transportation to the Colonies were brought here to quarry the vast quantities of stone required. A large temporary convict prison was built high above on Portland’s East Cliff.

Tourists came from far and wide to see the progress, as millions of tons of stone were laid.

In 1862 the Training ship Britannia “the nursery for our future admirals” was stationed here.

During the 1st World War  the Grand Fleet assembled in Portland Harbour before sailing to Scapa Flow. The old battleship HMS Hood was scuttled to permanently block the vulnerable South Ship Channel between the first two breakwater arms.

Carry on walking straight until you reach the restaurant The Boat that Rocks.  Outside here is where you can catch a ferry to Weymouth (and back). It runs daily in the summer months, weather permitting.

To the left of the ferry stop is a Mk 8 torpedo. The torpedo, nicknamed Tom the Torpedo acts as a reminder of Robert Whitehead’s now-demolished Torpedo Works factory, built in 1891, and situated on the northern shore of the harbour.

On the same bit of shoreline is the HMS Illustrious Memorial  remembering a disaster that has been described as “one of the biggest tragedies to befall the Royal Navy in peacetime history”.

Memorial to HMS Illustrious

On the night of 17 October 1948 a motor pinnace containing fifty-one liberty men from HMS Illustrious sank in the harbour with a loss of 29 lives. The pinnace was returning the men from shore-leave and left Weymouth pier during rough weather. It foundered due to the fact that the boat was overloaded, and that it had also failed to reduce speed or to turn back to Weymouth when it encountered rougher water on coming out  of the breakwater.
If you wander behind The Boat that Rocks you will see a  Lynx Display Aircraft  – a reminder of Osprey Quay’s former use as RNAS Portland

Retrace your steps back towards Portland Castle and take the side entrance that takes you to the small beach directly behind the castle.

Portland Castle from the harbour side.

Looking out onto the peaceful harbour today its hard to imagine it in wartime. With the outbreak of World War II, Portland was a natural target for German aircraft, due to the importance of island’s naval base. Between 1940 and 1944, the island was the target of 48 air attacks, in which 532 bombs were dropped. One of these air attacks was the bombing of the anti aircraft ship Foylebank at station in the harbour in July 1940. Leading Seaman Jack Foreman Mantle was a part of the ships company and was killed aged 23. His official citation is below, explaining how and why he was posthumously awarded the Victoria Cross.

Leading Seaman Jack Mantle was in charge of the Starboard pom-pom gun when HMS Foylebank was attacked by enemy aircraft on the 4th of July 1940. Early in the action his left leg was shattered by a bomb, but he stood fast at his gun and went on firing with hand-gear only: for the ship’s electric power had failed. Almost at once he was wounded again in many places. Between his bursts of fire he had time to reflect on the grievous injuries of which he was soon to die but his great courage bore him up till the end of the fight, when he fell by the gun he had so valiantly served.  London Gazette 3rd September 1940

Twenty-two bombs hit the ship and she  sank the next day. Over half of the ship company was killed. LS Jack Mantle VC is buried in the Royal Naval Cemetery in Portland, fittingly looking down over the harbour where he bravely defended the ship.

If the tide is low you are able to walk along the beach, through a boatyard and up a few steps into a narrow passage way leading you into Castletown. If its high tide you will have to take a longer route of following Liberty Road around the castle and then turning left onto Castle Road where you will reach Castletown. Stop outside the Osprey Leisure Centre.

You will notice on your right hand side that there are flats looming over Castletown – some of which are in desperate need of redevelopment. These were built in 1987 for the ratings and officers of HMS Osprey along with the Boscawen Centre (now the Osprey Leisure Centre). It was Portland’s largest building project since the construction of the Breakwater and Verne and  cost  £25 million but made redundant less than 15 years later when the  navy left Portland in 1995.

Ex-naval flats looming over Castletown – soon to be redeveloped.

Cross over to the flats – 2nd turning from the roundabout

Welcome to Castletown ..

Look up to Verne Hill which was an Iron Age Fort  that was strengthened later by the Romans. You will notice a bridge, just to the right of the Legacy Monument, and under this is the track of the old Merchants Railway.

Merchant’s Railway dominated the western part of Castletown. Opened in 1826, the Merchant’s Railway transported stone down from the quarries. When the stone arrived at the Incline Railway they were attached to a mechanism whereby empty trucks were pulled up the hill and the heavily loaded ones descended by gravity. The trucks were then pulled from the bottom railway line to one of the 11 persat Castletown by teams of horses. This carried on until the late 1930s. By this time road transport had made the old incline redundant.

The railway track is now history represented by a few stone sleepers on which the rails were carried – this track is not covered into day’s walk so retrace your steps back to the leisure centre and carry on walking into Castletown. 


Lookout for the Lerret, a traditional Dorset boat designed specifically for use off the Chesil Beach.  At first glance a Lerret appears to be like any other large wooden rowing boat. But look again. Where is the stern and why is the bottom flatter than a conventional boat? Find the answer on info board.

A traditional Dorset fishing boat known as a Lerret


Just past the Lerret you will find the newly opened  D Day museum,

D Day Museum www.castletownddaycentre.com

The entrance to the D Day museum is hard to miss as Sherman Tank guards the outside.

This museum, housed in an ex naval warehouse, tells the story of Portland and its role in D Day.It houses  a real Sherman tank, a 1944 American Dodge Weapons Carrier, a BSA 500 with sidecar and a full-size replica of a Spitfire as well as much more. The whole of Castletown area was the scene of a momentous and unprecedented gathering of thousands of the U.S. Army and their equipment for embarkation in dozens of landing craft on 5th June 1944.  Nearly 1/2 million troops and 144,000 vehicles left this port in a just a few hours. This was the eve of “Operation Overlord” assault on the Normandy coast area now best remembered as Omaha beach for the beginning of freeing France from its occupation under Nazi Germany.

Portland’s contribution was noted by messages from the United States including “You are the biggest little port in the world, you have been wonderful.”

Once you have finished at the museum walk towards Castletown Beach. From here you can see the Mulberry Harbours. These were perhaps the single greatest innovation that ensured victory for the Allies in the Battle of Normandy that followed D-Day. Without port facilities, the Allies would never have been able to build up their forces in France sufficiently to be able to withstand the German’s efforts to defeat them. A floating harbour that could be transported directly to France. Out of a total of 148 produced units, two still remain here  and are both listed buildings. They are 60 metres long, 20 metres wide, and 15 metres high. Each weighs 7,700 tons.

Mulbery Harbours as seen from Castletown Beach

Carry on down Drunkards Row

This is a one-sided terrace had been formed by 1864, and along this frontage a number of businesses and residential properties were established, including a custom house, coal merchant, chandler, barbers, post office, along with many hotels and pubs. All these pubs led to a reputation of rowdiness and the terrace became known as Drunkards Row.

Today Drunkards Row is an atmospheric street of past glories.

The Jolly Sailor – once a popular inn along Drunkards Row.

The Aqua Hotel – once the sailors mission

At the end of the row retrace your steps back to Portland Castle where this walk ends.


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