Welcome to Weymouth and Civil War Walk. This walk leads you through old Weymouth showing you the key locations of the town’s turbulent part in the civil war. But before we proceed it is advisable that you spend five minutes reading the introduction which explains why the Civil War happened and what that meant for Weymouth.

Why did the Civil War Happen

The long term cause was an argument over power. King Charles I believed in Divine Right, the idea that he was king chosen by God and that people should therefore obey him as they would God. Parliament, led by Oliver Cromwell, believed that as the elected representatives of the people they had the right to wield supreme political power. The relationship and disagreements between Parliament and the Crown rapidly deteriorated from 1640. Oliver Cromwell called for volunteers to fight the king. These Parliamentarians were known as Roundheads, partly due to their pudding basin hairstyles.

The Puritan Roundhead by johnPettie

The Roundhead by John Pettie.

The Kings supporters (Royalists) were often called Cavaliers.

Prince Rupert by anthony van dyck

Prince Rupert(nephew of Charles I) – an archetypical Cavalier, by A. van Dyck


A full scale war broke out in 1642.

The civil war lasted for seven years (1642-1649). It wasn’t a continuous war but a series of bloody battles around the country. It tore the country apart.

Weymouth and Melcombe Regis

Weymouth and Melcombe Regis were once two separate towns separated by water. Weymouth was the old town on the Nothe side of the harbour and Melcombe Regis was on the opposite side. There was hostility towards each other and frustrated by their constant bickering an Act of Parliament in 1571 united the two towns as the Borough of Weymouth and Melcombe Regis.

At the start of the Civil War Weymouth was occupied, without fighting, by Parliamentary forces, and military defenses were set up. These included the 14th century Chapel of St Nicholas which was converted into a fort. This fort stood on a commanding position on a precipitous cliff known as Chapelhay, and was reached by 70 steps from the street below. This was the largest and most strategically important fort in the area. Other forts were erected at the Nothe and Bincleaves, to protect the harbour and the bay. Earthworks were thrown up, some at the then northern entrance to Melcombe Regis, and others just a little north of the junction of St. Thomas Street with Lower Bond Street. Several drawbridges were built and town gates installed.

Contemporary cartoon of civil war

Contemporary cartoon of the Civil War

In February 1645 Weymouth was still in the hands of around 900 Parliamentarians, led by Colonel William Sydenham, and all seemed calm. But there was an undercurrent of royalist supporters waiting for their chance to rise, with the help of the Royalists who were in charge of Portland Castle.

This opportunity arose when King Charles I made contact with Sir William Lewis Dyve, who was Commander in Chief of Royalist forces in Dorset. The King commanded that Dyve capture both Weymouth and Melcombe Regis as he needed a port where he could land French Catholic soldiers to help him win the war.

Dyve contacted a small group of Weymouth Royalist sympathizers, led by a prominent merchant called Fabian Hodder. These Royalists then plotted with Sir William Hastings, the Royalist Governor of Portland Castle to capture Weymouth and Melcombe.

Communications between these different factions were difficult so some Weymouth women acted as couriers carrying messages to avoid suspicion. The bearers of Royalist messages from persons of high rank and importance were sometimes given ” tongue tokens,” as a proof of the genuineness of the bearers, when no written word could be risked. These tokens were tiny ovals of gold, small enough to be put under the tongue in case of need, with the head of Charles I on one side and his initials on the other.

Plundering of a Royalist household by roundheads.

Plundering of a Royalist household by Roundheads.

But more men were needed so Hodder scouted around Melcombe Regis and Weymouth offering men £5 if they would join him, and those that took the money were made to swear an oath: “You shall swear by the Holy Trinity that you will conceal the intended plot”. The password for the royalist conspirators was Crabchurch and they were told to tie a white handkerchief on their arm.

The plan was that the Portland Royalists were to attack and seize the Nothe and Chapel Forts while cavalry arriving from Sherbourne Castle under Sir Lewis Dyves would attack the town’s inland defenses.

The attack was to be at midnight on Sunday Feb 9th 1645.

When the morning of the 9th February came round, an order was given during Sunday Service, in an Portland church, that part of the Portland garrison and the Islanders should appear, with their arms, at the Castle at Castletown, by five o’clock in the evening of that day. The men having assembled, two companies were formed, under the command of Sir William Hastings, one to go by land and the other by water to Weymouth. Thus one company accordingly proceeded along the road by the Chesil Beach to Smallmouth. There was no bridge in those days at this narrow inlet of the sea ; it was crossed by means of a passage-boat kept by a ferryman on the Wyke side, and was known as “The Passage.” A Weymouth plotter had arranged with the ferryman to have his boat ready to row over the Royalists.

Meanwhile the other company sailed to the ancient pier (long since demolished), under the Nothe, then crept along to the Nothe Fort. The total number of the attacking party from Portland was small and did not exceed 120.
At Melcombe the plotters waited in the expectation that Sir Lewis Dyve was about to arrive and capture the town.

As midnight struck the surprise attack by the Royalists began and both the Nothe and Chapel Forts were quickly captured by the Portland Royalists. The Roundheads were forced to flee and take refuge in local houses. Within half an hour though the brave Parliamentarian Francis Sydenham(brother of William) led an assault to try and win back Chapel Fort. Leading from the front he charged the enemy and a fierce fight ensued. But to no avail. The Chapel Fort still remained in royalist hands and Francis Sydenham was mortally wounded as he came up the steps by the old wall. He died at dawn the following day aged 27.

civil war horses



Elsewhere things did not go so smoothly for the Royalists. Sir Lewis Dyve failed to show up and the waiting plotters went home. Melcombe Regis stayed in Parliamentary hands. It was not until the following day that Dyves’ 1,500 horse and foot army marched their way into Weymouth(not Melcome liked planned) forcing the outnumbered Roundheads to retreat to Melcombe, who raised the drawbridge between the two towns as they left.

house on fire

The night sky would of filled with smoke from the burning buildings

The Royalist guns fired constantly upon the Roundheads. Fire balls rained down from Chapel Fort causing much damage to local buildings. The sky filled with thick black smoke as the thatched roofs went up in flames . Sydenham appealed to stop the destruction but to no avail so Parliamentarians retaliated by using fire ships to set light to Royalist ships which then spread to more nearby houses.

Fre on a ship

Fire ships

A jubilant Dyves was certain that the Royalists would hold Weymouth and confidently expected to capture all of Melcombe in the following weeks.

But help was at hand for Colonel Sydenham. Vice Admiral Batten in his ship “The James” brought two Parliamentary ships into the bay and landed two hundred men claiming they were some of the toughest fighting men in the Dorset campaign
Over the next couple of weeks the Parliamentarians made a number of successful raids from Melcombe capturing supplies, horses and prisoners.

Unfortunately for Sydenham, Lord Goring(The Kings Lieutenant in Hampshire) was on his way from mid-Dorset to Weymouth; with him 3,000 horses, 1,500 foot and artillery train. Lord Goring and his crew were feared. Goring was known to be a very ambitious man who was not too fussed about what he had to do to advance himself and plundering with violence was part of the course. But he did not attack Melcombe immediately though arrogantly assuming he could take the small town at his leisure and instead rested at Dorchester for a few days.

Lord Goring

Lord Goring

On Tuesday 25th February Sydenham spotted a Royalist column. It was a gift from Goring to Dyves containing provisions. The Parliamentarians attacked and Dyve responded by sending out from Chapel Fort 100 infantry to give assistance. This left Chapel Fort unmanned. Seeing his chance, Sydenham lowered the bridge and 150 Parliamentarian Musketeers came charging out. A fierce battle eschewed. Many Royalists were killed or captured. With their superior numbers it is surprising they were beaten.
The humiliation for Dyve must have been unbearable as he tried to explain to an angry Goring exactly how Sydenham got the better of him. Dyve described the loss of the fort as a” strange misfortune.”Colonel William Sydenham now had two towns to defend with his small force of 1200 soldiers. The Royalists still held the Nothe Fort and a smaller one at Bincleaves.

On February 27th a patrol of Sydenham’s’ cavalry was approached by a roundhead soldier ,who had escaped from the prison at Dorchester and had important news for the Colonel. The man had overheard talk of an attack which was to happen that very night, at midnight, by Goring and his huge army. Sydenham made preparations for the attack.

Goring’s men arrived with drums beating and trumpets blowing.

Colonel Sydenham had set up a defensive line at the top of the old High Street at Boot Hill, near the Boot Inn, and once the main gate fell, Goring’s men hurtled towards them. The line held for a while but through sheer weight of numbers, gradually gave way and the Parliamentarians retreated back down the dark main street of Weymouth. The cavaliers thinking that victory was certain followed after the Roundheads, but within the narrow confines of the street Sydenham had set a deadly trap. At least two cannons were positioned at the far end of the street, and every window and doorway held one or more musketeers ready for action. The royalist force fell straight in to Sydenham’s ambush. Trapped in the High Street with canons being fired and lead shot muskets being fired many of the royalists did not stand a hope. As many as 70 were killed and many more wounded, and Sydenham’s men now rushed out and entered in to a deadly hand to hand struggle with Goring’s shocked troops who turned and ran. Blood is said to off run down the street flowing into river turning it a gruesome red.

Sydenham then turned his attention to Chapel Fort which was under attack by the Cavaliers. On his horse he led his men to further battle. They chased the panicking Royalists men back along the dark, cold quayside. As many as 250 of them died mostly by falling into the icy winter waters of Weymouth Black Hole where Hope Square sits today. William Sydenham had his horse shot from beneath him during the fight but even that did not stop him and he was still able to rally his men. Not one part of Weymouth or Melcombe had fallen to Goring, who, along with his dispirited force had now retreated to Wyke to lick their wounds. From there they marched out of Dorset towards Taunton.


Victorious Parliamentarians


The Royalist troops holed-up in the smaller forts of Nothe and Bincleaves – which had not been attacked –appear to have left in a hurry leaving their possessions and most of their guns.

Against the odds the Parliamentarians had won.

With the Royalist threat finally gone it was now time for retribution. Several of the original conspirators were caught and imprisoned. On the morning of March 3rd, 1645 soon after daybreak the prisoners were led to the Nothe Gallows to be hung. Many townsfolk trailed along behind them.

Possibly the most famous image of the Civil War - Yeame's "When did you last see your father" - an imaginary Royalist household being questioned by Parliamentarians.

Possibly the most famous image of the Civil War – Yeame’s “When did you last see your father” – an imaginary Royalist household being questioned by Parliamentarians.

At the end of all the fighting the people of Weymouth and Melcombe were left worn out, hungry and filthy. Retreating soldiers had plundered houses. Their towns in ruins, the narrow streets lined with their burnt out homes. There was much clearing up to do. Lighters were used to carry away the town refuse which had accumulated during the siege and many of the earthworks were removed. The chapel which had been used as a fort was beyond repair and was demolished and the materials sold. The cleaning up was still taking place in August as help arrived from Sherborne and stayed for 12 weeks with their shovels and wheel barrows. In October a review of the damage of the town was ordered and houses and walls were pulled down.

The recapture of Weymouth was considered so important to the Parliamentary cause that it was marked with a special thanksgiving in London on the 12th march attended by the Lord Mayor, the city of Alderman and representives of the both of Houses of Parliament.

The Parliamentarians controlled Weymouth for the remainder of the Civil War.


Start: The Tudor House, Trinity Street – Hope Square

Finish: Maiden Street

Distance: Approx 2km

Terrain: Mainly flat but there is a couple of  steep slopes and steps.

Tudor House

This house would have bore witness to the Civil War. One can only imagine if the occupants had anything to do with the fighting . Most residents would have attempted to keep out of the troubles – it is a possibility that the occupants would have fled to safety and taken their valuables with them in case of plundering from troops.
The Tudor House is one of Weymouth’s treasured buildings and is thought to have been a merchant’s property. It originally fronted an inlet from the main harbour, allowing ships to be moored alongside. The building eventually became derelict having been empty during the Second World War and suffered bomb damage.
In the 1950’s a local architect acquired the property and restored it, which he furnished in the style of an early seventeenth century home of a middle class family. The house was bequeathed to the Weymouth Civic Society. A tour of the house gives a fascinating insight into 17th Centaury life. Guides describe the domestic daily life of the times, including furniture and clothing, cooking and serving of food, lighting and candle making.

Weymouth Tudor House

The Tudor House. Take a look at the roof guttering – rain water would of flowed straight into the harbour.


Hope Square is built on reclaimed land. At the time of the Civil War it was an opening to the sea, known as the Black Hole or the Ope Cove, and water would have reached as far as the pavement outside today’s Red Lion Pub. This is final resting place for the 250 Royalists who were trapped and driven to their deaths after being chased by Parliamentarians along the quayside on the 27th February 1645.

Brewers Quay

Brewing had taken place in Weymouth, and specifically Hope Square, since the 13th Century and was the oldest local industry. Hope Square  had a brew house here for centuries due to the fact there was a spring at Chapelhay and barley at Radipole. The buildings you see today known as Brewers Quay which was built 1n 1903/4 as Hope Brewery for John Groves. Devenish also set up business here. Brewing ceased in 1984 and today forms a conservation area.

brewers quay - weymouth

Brewers Quay – once a brewery but now converted into shops.

Opposite Brewers Quay is Pilgrim House on the corner of  Hope Street. Even though Pilgrim House is an 18th Century building, it has been suggested that the indentations on the end wall (right of the post box) were caused by a canon fired from Chapel Fort, possibly during the Civil War.

Pilgrim House in Hope Square - weymouth

Pilgrim House in Hope Square


Canonball damage on Pilgrim House, Weymouth

Indentation – caused by a cannonball?

At number 21 Hope Street is an interesting 17th century building – during the years of the Civil War many of the houses would have had similar features.

21 Hope Street weymouth

No 21 Hope Street (blue door) – a charming 17th century building.

Once you have explored the area head towards Trinity Street and take the right turning up St Leonards Road, following around the first steep turn to the right called Herbert Place. Be careful here as  there is no pavement for a few metres.

This leads into Franchise Street.

In the corner of a private garden, visible from residents parking, is a small chapel, built by a cleric who once lived in the property. This tiny chapel was possibly built on the site of a Chapel of Ease used by pilgrims travelling to Spain. Pilgrims would make the uphill trek to this shrine to pray for safe passage. The pilgrims would leave an offering usually gold or other precious item. When Cromwell’s forces took Weymouth the priests hastily buried the gifts to save them from falling into Parliamentarian hands, and planned to reclaim the booty when safe. But the priests never returned as St Nicholas Chapel as it was too badly damaged. The treasure has yet to be found!

Chapel of Ease used by pilgrims - franchise Street - Weymouth

Chapel used by pilgrims

Turn right along Hartlebury Terrace, then left into Trinity Terrace. Here are great views of the Harbour.

Views over the rooftops of Trinity Terrace

Views over the rooftops of Trinity Terrace

At the end of the terrace is Chapelhay Tavern. This building dates from the Georgian era but it is thought this building was refaced in the 17th Century, thus suggesting a tavern has been here for hundreds of years.

Chapelhay Tavern - Weymouth

Chapelhay Tavern

Turn onto the slope which runs alongside the skittle alley of the tavern. Go down the steps and turn left and take flight of steps up to Chapelhay Street which is one of the oldest streets in Weymouth. In 1645 it would have been known as St Nicholas Street as it led to Weymouth’s first chapel dedicated to St Nicholas, the patron saint of travelers. The Chapel was originally built in the 14th Centaury to combat French raiders who attacked the town on Sundays when most townsfolk were worshipping at All Saints in Wyke, which was a good mile away.

The chapel suffered badly during the Civil War when it was used as a fort and was destroyed not long after

There have been reports of ghostly happenings near here late at night with the sound of heavy hasty footsteps accompanied with beating drums and angry shouting with the sound of gunfire nearby. Could this be the sound of the Civil War reverberating through the years?

Walk along the top of the old wall and Chapelhay Gardens. Repair work to stabilize the wall(some parts of the wall are Tudor) and gardens has recently been carried out but unfortunately the gardens have yet to be completed. Hidden amongst the undergrowth are a few of the original steps that led from a ferry at the river to St Nicholas Chapel.

view from Chapelhay

Views from the old wall and Chapelhay gardens

During the fighting this area would be used as a strategic place with canons trained on the bridge and town below with wide reaching views. It is somewhere near here that Francis Sydenham was mortally wounded.

View from Chapelhay Street

View from Chapelhay Street

Three hundred years later the area was to suffer again after bombing raids during the Second World War. Extensive damage was done to buildings and there were heavy casualties.Today a housing estate dominates the area.

Follow the road until you reach the Old Town Hall.

The Old Town Hall

This building was built in the 17th Century, but was renovated in 1774 and again in 1896.

The Old Town Hall Weymouth

The Old Town Hall

This is where the day to day business of running the old town of Weymouth was carried out. During the Civil War it was used as a central command post. It is possible that there were tunnels running between the hall and St Nicholas Chapel.

The bell tower is 17th Century but some of the brick work may be even earlier. The bell that was in the turret is dated 1633 with initials, R.P. – which stands for Richard Purdue who cast the bell, originally for use in Radipole Church but ended. By the 1970s the bell sat redundant on the floor of the bell tower with a chain around its canons to secure it. Eventually it was moved to Weymouth Museum but thanks to the “Guardians of the Old Town Hall”, a community group, the bell was returned and in August 2014 it tolled again.

Today the Town Hall is used for community events.

High West Street

Chapelhay Street blends into High Street West. This small road was part of Weymouth’s original High Street. Here stands a terrace of 18th and 19th century houses. Amongst these houses there is a gap behind some gates which was the access to where the houses of High West Street Court once stood.

A survey of Dorsetshire in 1630 says of Weymouth that it “consists chiefly of one street which for a good space lyeth open to the sea and on the back of it riseth an hill of such steepness that they are forced to clymbe up to their chappell by 80 steps of stones”.

The most bitter fighting, in the early hours of 28thFebruary 1645, was here. The Royalists forced their way into the streets and alleys of this area. But Sydenham was waiting with muskets and canons. The noise must of been terrifying on that dark night. The Royalists were chased along the harbourside, many to deaths in the freezing, black water.

Love Lane

Just past the Town Hall on the left is Love Lane – a narrow pedestrian through fare linking High Street West and franchise Street. There has been a street here since medieval times and today is lined with quaint little houses.

Love Lane Weymouth

Love Lane – built upon a medieval street pattern

The Old High Street continued down past the Boot Inn until it merged with Trinity Road at Holy Trinity church (built 1836) at the end of the Town Bridge. Trinity Road itself was once a continuation of the High Street and carried on into what is now Trinity Street at the Old Harbour.

The Boot

The Boot is the sole survivor of four inns that originally existed in the High Street. An Inn or alehouse has stood on this site since 1346. Today most of the building is 17th Century but it still retains an old peat floor cellar, ideal for keeping ale cool and has walls older than the rest of the building. The interior of the pub still has its original beams.
It has been suggested that the name `Boot’ be used in the Middle Ages in association with shoemakers and that the old Tannery and Cobblers shop that stood on the site of the nearby Municipal Building could account for the name. Or it could be linked to the common welcoming wooden boot sign that used to be displayed for travelers outside Inns letting know that they could use the washing facilities.

The Boot Inn Weymouth

The Boot Inn – well worth a visit!

At the time of the civil war it was a waterside inn as North Quay Road would not have existed. It was popular with smugglers who arrived by boat which was guided by a lit lamp in the front window and would have hauled their boat and cargo up a slipway which survives as a small road to the side of the pub.

This pub has the dubious distinction of being the most haunted pub in Weymouth. There is a ghost who sings sea-shanties and another one dresses as a coachman. Local legend has it that one of the ghosts is a lady who sits in the corner of the pub waiting for her lost lover.

Head towards North Quay

North Quay

Below High Street West today is a new development of retirement homes and nothing now remains of Jockey Row or Silver Street with their haphazard cottages nestled in above high tide level. and close by the municipal buildings of

An unusual house of Tudor origin stood at No. 4 North Quay, near where the municipal buildings now are. The was known as the Harbourmaster’s house and if you look in the harbour you may see its remains. During redevelopment of the area after the 2nd World War the demolishers were at a loss with what to do with the rubble from the house. They came up with the easiest solution – throwing the bricks into the sea. The only object saved was the staircase which was installed in St Ann’s Church, Radipole.

Rubble from the Tudor House is lying in the inner harbour

Rubble from the Tudor House is lying in the inner harbour

At the back of the car park of the municipal buildings can still be seen some evidence of the former life of this area in the form of old  Tudor Walls.

Old Tudor wall weymouth

Behind the council offices are remains of the old Tudor Wall. Above is Chapelhay, where once St Nicholas Chapel stood.

Below the city wall a Royalist surgeon called Richard Wiseman(who later became father of surgery) bared witness Parliamentarian attack on Chapel Fort on the 25th February. He was treating a wounded royalist soldier at the time of the attack and he later wrote ‘as Sydenham’s troops attacked, I was dressing a wounded man in the town almost under the Chapel Fort and hearing a woman cry, ‘fly, the Fort is taken’, I turned aside a little amazed towards the line, not knowing what had been done, but getting up the works I saw our people running away, and those in the Fort shooting at them. I slipped down this work into a ditch and got out of the trench; and as I began to run hearing one call ‘Surgeon’, I turned back and seeing a man hold up a stumped arm, I thought it was an Irishman whom I had absolutely dismembered, whereupon I returned to help him. We ran together, it being within half a musket shot of the enemies’ Fort, but he outran me quite”.

Walk to Holy Trinity Church and cross over the town bridge.

The first bridge here was built in 1597 and was present in the Civil War. It had 17 arches and a draw bridge and needed 30 Great Oak trees from the New Forest to construct it.

Custom House Quay

Take the steps down from the bridge (by the  Rendevous  Pub) onto the Quay.

Like today there would have been inns on the Quay. A survivor of the 17th Century, and possibly a watering hole for the Parliamentarian troops, is The Ship. It has extended over the years and recently refurbished.

The Ship Inn Weymouth

The Ship Inn

Turn right at the side of The Ship Inn into Maiden Street. Find the fire damaged Methodist Church on the  corner of St Maiden Street and St Edmund Street. Look across road at the Jacobean building. Can you tell what is lodged in the wall? It is a cannonball most likely to of been fired from Chapel Fort by the Royalists during their siege of Weymouth. This area was a target for intense continual bombardment, due to the fact that Colonel Sydenham headquarters were nearby in what is now known as Governor Lane.

Cannonball in the building wall weymouth

Cannonball fired from Chapel Fort

The author Grace Pearce in Down Wessex Way recounts a local legend of the haunting of this building. In the 1790s the house was occupied by a tradesman called Rudge who had a butchers shop on the ground floor (were the public toilets now are). He lived with wife, their three children and an elderly servant. A woman wearing a red shawl and white cap kept appearing in the bedroom and pointing at a inner wall. She looked like the lady in a portrait that was hanging up in the parlor which was Rudge’s great grandmother who had lived in the house during the 1645 siege. Mrs. Rudge became very nervous and demanded that her husband knock down the bedroom wall. They discovered a small room with a stool, a hat and a chest containing skeleton wearing armor! Mr. Rudge believed it was his great grandfather who was a Royalist solider and had gone missing during the Civil War. He supposed that friends had brought him here planning to bury him when all had quietened down. The soldier was buried and the hidden room cleaned and window put in and used as dressing room adjoining the large bedroom facing St Edmund Street. Rudge’s neighbours also gossiped that of pieces of gold must have been found as The Rudges became very wealthy not long after!

And on that note this is where the walk ends – I hope you enjoyed it.


Hutchins: History of Dorset Vol II

Eric Ricketts: The Buildings of Old Weymouth Part II

Maureen Attwool & Jack West: Weymouth An Illustrated History

W. Bowles Barrett: Proceedings of the Dorset Natural History & Archaeological Society Vol 31,1910 

Alex Woodward: Haunted Weymouth


Leave a Reply

Your email address will not be published. Required fields are marked *

Follow me on Twitter

Contact us

Sending your message...