Forest of Dean Local History

The Civil War Around the Forest of Dean


Dean Local History

Civil War 1643

Civil War 1644

Civil War 1645

Civil War 1646

Local Castles


Sir John Wintour had re-occupied Newnham, and fortified the church with four pieces of ordnance, so that the West of the County now seemed protected against attacks from the Gloucester garrison.

However Massey delighted in surprising his enemies and making his power felt where he was least expected. He had built and launched a vessel on the other side of the Severn which was capable of carrying a sufficient number of men to disturb and plunder the opposite bank.

Having manned it with seamen and musketeers, the vessel sailed down to Chepstow in January 1644. The soldiers rushed on shore, and, before the town could recover from its surprise, seized and carried off most of the officers of a regiment of horse raised by Lord Herbert, who were billeted at the George Inn.

The local burial records show that 'Captain Carvine who was killed in his chamber in the George by certaine souldiers who came from Gloucester and was buried the 20 of January.'

There is another entry for 1644: "a souldier dyinge att the George, his name unknowen, was buried the 26 of February" - and yet another for March 7th for a soldier who also died at the George.

To add to their victory, the small force also captured a supply ship laden with stores which was on its way from Bristol to the Royalists garrisoned at Worcester.


Chepstow's Town Gate originally built, with the wall, in the late thirteenth century, was the only landward entrance to the town through the Port Wall, and a point where tolls for those visiting the town and its market were collected. It was also an important position for troops to be placed during any conflict.

The George was first recorded in 1624, with the landlord named as William Jones. 

The inn and the Gate House are positioned on either side of the town wall, and may have been linked by tunnels. 

The town walls were defended at irregular intervals by ten round towers, and the entrance to the town was through the large gate house, still standing, and now the Town Council office, which was given to the bailiffs by the charter of 1524 to be used as the town gaol.

Except for some 20th century destruction for car parks and the A48, much of Chepstow's Port Wall remains intact. The construction of the railway in 1846 caused one breach, and a length south of the railway line was demolished when the National Shipyard was constructed in 1916. 

Interesting Discoveries at the George Hotel.

Whilst proceeding with the work of rebuilding the George Hotel, Chepstow, last week, one of the workmen felt his leg slipping through a crevice in the stone floor of one of the kitchens, and on closer inspection it was found that beneath the floor was a stone well thirty feet deep (on being tested) and five feet in diameter, containing one foot of water. No one can remember this well ever being used, and it must have lain there undiscovered for a century or more. 
A short time previous to this, a roomy arched cellar, perfectly dry, but empty, was discovered below another room.

This also bore the appearance of not having been used for many years. 
Whilst knocking down some masonry at the back, near the old Port Wall, a subterranean passage was discovered, leading in two directions, - one presumably towards the river and the other towards the Castle; but after proceeding for some distance (with the aid of lamps) the way was found blocked with fallen stone and earth. 

This latter passage was probably utilised during the stormy period immediately preceding the Commonwealth as a secret means of egress from the Castle to the river for the soldiers of the garrison; and it seems a pity, from an antiquarian point of view, that it should have been closed up without further investigation. On the other hand, of course the builders of the new structure did not include in their contract the cost of such investigation, and have received no instructions to stay the work of erection pending further enquiries.'

Chepstow Weekly Advertiser 22nd July 1899


Towards the end of January, 1644, Wintour captured Westbury and Huntley for the Royalists. He made a secret march from Newnham and aided by the treachery of a bribed Roundhead officer, Captain Thomas Davis, surprised Huntley House, taking the small garrison prisoners, and then moving on to Westbury, and capturing that post. He ended up with 129 prisoners, plus a good supply of arms and ammunition. His force then captured the garrison at Littledean.

Captain Thomas Davis accepted a bribe from Wintour and put him in possession of the garrisons of Huntley and Westbury. This they took seriously to heart being a loss of eighty men with their arms. Davis was posted in military form on the gallows at Gloucester as a villain and a traitor; and the Lord General was requested that his name might be published with equal ignominy in all the parliamentary garrisons.

In March Prince Maurice was appointed the King's Lieutenant General of the West and on March 27th Wintour was then officially appointed, by the King, to be Royalist Governor of the Forest of Dean.

His 'spymaster' in the Forest area was Edward Clarke of Newent, a tanner and provisioner, who used a team of messengers and spies to provide information on troop movements, and the locations of parliamentary supporters suitable for plundering.
In May 1644, taking advantage of Sir John Wintour's absence at some action over at Ross-on-Wye, Colonel Massey started a drive from Gloucester against Royalist garrisons.

On the 7th he recaptured Westbury and Littledean, and on the 8th, Newnham.

About Westbury, Sir John Corbet wrote:—“Here the enemy held the church, and a strong house” (understood to be Mr. Colchester’s) “adjoining.” “The Governor (Colonel Massey), observing a place not flanked, fell-up that way with the forlorne hope, and secured them from the danger of shot. The men got stooles and ladders to the windowes, where they stood safe, cast in granadoes, and fired them out of the church. Having gained the church, he quickly beat them out of their workes, and possest himself of the house, where he took about four score prisoners, slaying twenty others, without the losse of a man.” 

At the same time Massey sent three troops of Colonel Purefoy's horse and a company of dragoons, under Captain Gainsford, to deal with the garrison at Littledean. They took the Royalists completely by surprise.

Lt. Colonel Congreve was the Royalist Governor of Newnham garrison. It appears that the Littledean skirmish, in which he and Captain Wigmore were later killed, started in the village.Naas House, Lydney

“Here,” says Corbet, “the governor’s troop of horse found the enemy stragling in the towne, and, upon the discovery of their approach, shuffling towards the garrison, which the troopers observing, alighted and ran together with them into the house, where they tooke about 20 men.

Neere unto which guard, Lieutenant-Colonel Congrave, Governor of Newnham, and one Captain Wigmore, with a few private souldiers, were surrounded in some houses by the residue of our horse. These had accepted quarter, ready to render themselves, when one of their company from the house kils a trooper, which so enraged the rest, that they broke in upon them, and put them all to the sword: in which accident, this passage was not to be forgotten that expressed in one place an extreame contrariety in the spirits of men under the stroke of death: Congrave died with these words, ‘Lord receive my soule!’ and Wigmore cryed nothing but ‘Dam me more, dam me more!’ desperately requiring the last stroke, as enraged at divine revenge.”

The spot where these officers fell is believed to have been at Dean Hall, in the dining-room, and near the fireplace.


Colonel Massey followed up these exploits by moving the whole force to Littledean that night. The next day, Saturday May 8th 1644,  they marched towards Newnham where the Royalist defences were centred around the church where there were earthworks and a small fort armed with four cannon plus a good supply of arms and ammunition. Corbet relates - “a strong party of Sir John Winter’s forces kept garrison in the church, and the fort adjoining,” (on a spot which has been turned lately into public pleasure grounds,) “of considerable strength, who at that instant were much daunted and distracted by the losse of Congrave, their governor.

Our men were possest of the town without opposition, and recovered the houses, by which they got nere the workes. The Governour (Massy) commanded a blind of faggots to be made athwart the street, drew up two pieces of ordnance within pistoll shot, and observing a place not well flanked where he might lead up his men to the best advantage, himself marched before them, and found that part of the work fortified with double pallisadoes; the souldiers being provided with sawes to cut them down, and having drawn them close within a dead angle, and secure from their shot, and drawing the rest of his forces for a storme, the enemy forthwith desires a parley, and to speake with the governour, which he refused, and commanded a sudden surrender.

In this interim some of the enemy jumpt over the workes, and so our men broke in upon the rest, who ranne from the out worke into the churche, hoping to cleare the mount which we had gained. But our men were too nimble, who had no sooner entred the mount, but rushed upon them before they could reach home, and tumbled into the church altogether. Then they cryed for quarter, when, in the very point of victory, a disaster was like to befall us: a barrell of gunpowder was fired in the church, undoubtedly of set purpose, and was conceived to be done by one Tipper, a most virulent Papist, and Sir John Winter’s servant, despairing withall of his redemption, being a prisoner before, and having falsified his engagement.

The powder-blast blew many out of the church, and sorely singed a greater number, but killed none.

The souldiers, enraged, fell upon them, and in the heate of blood slew neere 20, and amongst others this Tipper. All the rest had quarter for their lives (save one Captaine Butler, an Irish rebell, who was knocked down by a common souldier), and an 100 prisoners taken. The service was performed without the losse of a man on our side.”

The prisoners taken included two with the rank of captain. The booty included - 'one great wall piece of 8 foot long, a good store of granadoes and some fire workes, 8 barrels of powder, 60 skeins of fine match, with good store of great shot for the guns, besides much in the way of provisions and 40 horses.'

Massey then moved on to Lydney hoping to get Whitecross to capitulate while John Wintour was away.

He had not counted on the courage of Lady Wintour who answered his summons to surrender with the following - "Sir,-Mr. Winter's unalterable allegiance to his King and Sovereign, and his particular interest to this place, hath by his Majesty's commission put it into this condition, which cannot be pernicious to any, but to such as oppose the one and invade the other; wherefore rest assured that in these relations we are, by God's assistance, resolved to maintain it, all extremities not withstanding. This much in Mr. Winter's absence you shall receive from Mary Winter." 

Realising how heavily defended Whitecroft was, and receiving intelligence that Sir John Wintour and Colonel Mynne were already at Coleford, he withdrew his forces to a position on an adjacent hill, and waited in vain for their approach. He finally marched his tired troops back to Gloucester having set fire to a large amount of coal stock, and some of Wintour's forges and furnaces.

Nothing is reported about Sir John Wintour in the Forest of Dean during the next few months. One source has him escorting the heavily pregnant Queen Henrietta Maria who left Oxford to journey home to France via a Cornish port, and had arrived in Exeter on 1st May 1644.

Her daughter, Princess Henrietta Anne, was born there on the 16th June 1644 at a time when the Parliamentary forces led by Lord Essex were threatening the west. It is believed that 15 days after the child's birth, hearing a rumour that Essex had placed a price on her head, she left her sickly infant daughter to be cared for by her governess, Lady Dalkeith, and slipped out of the city bound for France. She was said to have been accompanied by her physician, her confessor, a lady-in-waiting, and Sir John Wintour. The party apparently had a very narrow escape. 


When Prince Rupert sent officers to South Wales to raise an army, some were offended by the high-handed conduct of the natives who made it plain that they preferred to be led by Welsh-speaking officers. One officer, Sir Thomas Dabridgecourt from Hampshire, on learning he was to be posted from Bristol to Ludlow, wrote from St. Pierre, near Chepstow on 11th of March 1644, "If Your Highness shall be pleased to command me to the Turk, or Jew, or Gentile, I will go on my bare feet to serve you; but from the Welsh, good Lord deliver me. And I shall beseech you to send me no more into this country, if you intend I shall do any service, without a strong party to compel them, not to entreat them. And then I will give them cause to put me into their Litany, as they have now given me cause to put them into mine".


Colonel Nicholas Mynne (1616 - 1644). was a dynamic Royalist leader and the commander of a regiment of Irish infantry raised by the Irish Catholic aristocracy in the South. They were apparently ruthless fighters who regarded the Royalist cause as having a “Catholic” dimension against the “Protestantism” of the Parliamentarians.

Mynne, for a short time Governor of Tewkesbury, was captured when Massey retook the town on 4th June 1644.  He was freed within weeks apparently exchanged for a Parliamentarian officer of equal status.  In July he was again back in business and while Massey was wreaking havoc in the Forest of Dean for the Parliamentarians, Mynne started to devastate the countryside around Gloucester for the King, “with fire and plunder, (by) running cattle and burning the corn in the fields - it being near the time of harvest.” Corbet described Mynne as “a serious and active enemy; a perpetual terror to the countryside”.

Mynne, supplied with regular intelligence from the Newent based spy, tanner Edward Clarke, thought that Massey's constant absences from his home base weakened Gloucester's defence capability and offered opportunities that he should not be slow to take advantage of.

To maintain his supplies Massey had to make constant forays, most of which were successful. Mynne was determined to take Gloucester and his system of continued fighting had greatly reduced both Massey's forces and resources. Mynne accordingly made his plans to assemble at Eldersfield all the forces he could muster, including a party from Worcester, to take Gloucester.


The Battle of Redmarley. On the 26th July, Mynne advanced to Hartpury, on the way to Gloucester.

Massey saw the move as dangerous and should be halted at once. Collecting all his available men, and calling in part of the Tewkesbury garrison, he got together what he hoped was a sufficient force.  Late that evening, he marched out and surprised an outpost of Mynne's at High Leadon, driving off some and taking others prisoner.

After apparently getting lost, and wandering about for some time in the dark, Massey halted his men at Eldersfield which was only two miles from the Royalist encampment.

In the early morning of August 2nd 1644, Mynne's drummers, by beating the reveille, disclosed the position of his force to Massey.

At Redmarley Colonel Mynne had drawn up his men, 850 infantry and 160 cavalry, in some enclosures, and lined the hedges with his musketeers, and was waiting for the large force of Worcester men to join them. Unfortunately they had been delayed by fog and Mynne soon ran out of time.

On the fog lifting, Massey advanced his men with two bodies in order of battle. Colonel Hurley led the van with three troops of horse, supported by Captain Backhouse with another three troops. On the flank of the horse were a body of infantry. The rear was brought up by another troop of horse and infantry and the reserves stationed in the village of Redmarley.

Massey at once began to attack the right flank and front. He drove the Royalists out of the enclosures and from the hedges, put the horse to flight, broke into the foot and shattered the whole body.

Mynne, with 130 of his men, fell fighting, and 30 officers, 1 sergeant, and 200 soldiers surrendered; the remainder making off at  top speed towards Ledbury.

At the moment when Massey had routed Mynne, Colonel Passey, the commander of the Worcester Royalist troop, rode up asking for orders. He was then wounded and left for dead. His men, however, continued to advance but had halted when they saw the bulk of Mynne's horse fleeing in disorder. They were not long left in uncertainty. Massey seeing the superior force, retired quickly.

The Worcester Royalists, now leaderless, and uncertain of what to do, remained halted, giving time for Massey, with his 231 prisoners, to quickly vacate the area.

Such was the battle of Redmarley. The fog had proved exceptionally fortunate for Massey. He later admitted that had the Worcester men arrived a little earlier, he probably would have been destroyed.

Mynne's body was conveyed to Gloucester and buried there with full military honours.


The Royalist defences at Beachley near Chepstow. Around this time Prince Rupert moved to the area. His aim was to collect together all the Royalist regiments from Herefordshire, South Wales, and Worcestershire to secure communications and supplies to Royalist-held Bristol. He sent 500 troops to Beachley, near Chepstow, to reinforce Offa's Dyke and dig in a defensive trench between the two rivers. A part of Chepstow bridge was destroyed to cut off access from the Forest of Dean to Chepstow.

In mid-September Massey's intelligence sources relayed that Yorkshireman Marmaduke Langdale's Northern Horse, under the command of Colonel Tuke, was about to join Prince Rupert at Bristol using the Beachley/Aust ferry. Chepstow Bridge before its removal in 1816. That crossing-point had taken on a new and strategic significance for the Bristol based Royalists as their opponents now controlled all the River Severn crossing points between Newnham and Tewkesbury.

Rupert sent over between five and six hundred cavalry and foot soldiers. He also had a number of warships anchored in the area but they were only of very limited use during low tide.

John Wintour began supervising the digging of extensive defences with a trench between the Wye and the Severn.

Colonel Massey did not want this bridge-head between Bristol and Chepstow to be established and was determined to destroy it.

After only four days,with 600 horse and foot, he advanced on the defences and overnight his musketeers faced the enemy. Because his position was within range of some Royalist warships, he was forced to wait until the tide went out and render their cannons ineffective.

Morning came and the tide turned, and with its lowest ebb came also the opportunity that he desired. Spectators of this trial of valour were not wanting. Rumour had attracted a multitude on the Monmouthshire side, who crowned the heights and beheld the scene in safety.

Ten chosen musketeers crept along the hedges, and received the first volley of the Royalists; but before they could re-load, ' the governor,' says the historian of his exploits, gave the signal by the discharge of a pistol, on went the forlorn-hope, and the reserve following, the trumpets sounding, and the drums beating, run up the works, rushed in among them, and fell upon the hack, when the whole and each part of the action was carried on without interruption, and the soldiers went up in such a regular march, and so great solemnity, that it seemed more like the pomp of a triumph then the confused face of a fight.

Of the enemy some were killed, and the rest taken prisoners, besides some few that recovered the boats, and many of them that took the water were drowned. The guns of the vessels kept up a steady fire during the tumult, but owing to their low water position, the shot were spent in vain. Rev. John Webb 1879

After the battle and destroying the defences, Massey had to withdraw, having deciding that he was unable to permanently secure Beachley as it was so vulnerable to gunfire from the Royalist ships.

Soon after that triumph he was pleased  to receive some useful reinforcements from the Earl of Denbigh.

The Earl supplied eleven troops of horse, and four hundred foot soldiers. This gave Massey the strength and confidence to march on Monmouth. 

On September 24th, 1644, he led his troops north, where, with the aid of Lt. Colonel Kyrle, he captured Monmouth. Kyrle was originally a Parliamentarian but changed sides after the Royalists captured Bristol.

He had apparently been recently caught by Massey at High Meadow, near Coleford, and thought it an ideal time to again change sides rather than be treated as a traitor.

Massey sent Kyrle ahead of the main force in front of a troop of horse. Colonel Holtby, the governor of Monmouth, allowed what he thought was a body of fellow cavaliers into the town and was immediately faced with a demand to surrender. A fight broke out when the incomers attacked the guard and, in the wet darkness, most of the Monmouth garrison, including Colonel Holtby, managed to escape.

Around this time, Sir John Wintour, with his enemy otherwise engaged, decided to re-occupy Beachley utilising his own 100 troops, an extra 400 from Bristol, and some reinforcements from Prince Rupert. Learning from the earlier battle when the warships were rendered ineffective by the low tide, he had extra cannon from Chepstow placed on the Welsh bank of the Wye. Defences were again dug and lined with iron-tipped pallisades. His warships also stood by.

At midnight on the 13th of October 1644, Colonel Massey left Monmouth with eight troops of horse and 100 musketeers. He made his way to Clearwell to join up with men from his Newnham garrison.

Early the next morning, and with the tide out, they again attacked the Beachley defences.

During the fierce fighting that followed, 30 Royalists were killed and 220 taken prisoner. Some were drowned, and a few, including John Wintour, escaped to the ships.

Massey at midnight drew out 100 musketeers, and with 8 weak troops of horse from Clearwall, and the garrison of Newnham, beat up their ambuscades, drove them into their works, and kept them on the alert the following night. Then, as before, at lowest ebb, and break of day (Oct. 14), with a very inferior force he approached to storm, and found them ready to receive him, and stronger within their fortifications than six times their number in the open field.

Once more putting himself at the head of his forlorn hope in the face of their fire he burst through their palisades. At this critical moment, in the act of forcing his horse over the hedge, he was unseated and tossed headlong among them.

A musketeer discharged his piece at him without effect, reversed it, and with the but-end dashed his helmet from his head. His men, however, by degrees were presently with him. Colonel Harley came up and remounted him. Kyrle followed with the whole body, and a desperate encounter took place, which was soon decided in favour of the assailants.

They slew 30, and took 220 officers and soldiers. Many rushed into the water towards the boats: some were drowned.

During this confusion of fighting and flying, killing and surrendering, Wintour resolutely kept his ground awhile with a pike in his hand near the edge of a cliff above the Wye. Kyrle first discovered him, and called aloud to his men: ' That is Wintour ; pistol him.' And while amazement riveted the attention of all who witnessed the hair's-breadth escape, he, neither fired at nor followed, by scrambling or rolling down a precipice supposed impracticable to man or horse, plunged into the river. ^ His horse, however, was taken; and as he seemed to sink beneath the surface he was supposed to have perished; till within a few days it was announced that he had been seen at his ease walking in the streets of Bristol. Rupert was to have been at Beachley the night after this affair. His tent was up, his bed made ready, and he afloat expecting to land at the next high tide. The place itself was found to be of no use to any who were not masters of the sea; accordingly the winners resolved in a council of war that every building should be levelled, and every tree and hedge cut down.^ ' [The place is called 'Wintour's Leap' to this day, though the origin of the name appears to be forgotten.]  Rev. John Webb 1879

After this battle, Massey ordered that, as a defensive measure, all buildings on the Beachley peninsular would be demolished.


With Massey otherwise engaged in the Cotswolds, the Royalists from Raglan recaptured Monmouth on 19th November.

When the Parliamentary commander returned he set up a number of garrisons in the Forest. On the outskirts of Lydney, Soilwell House and the mansion at Naas, were manned and fortified to counter Wintour's Whitecross garrison, and St. Mary's Church tower used as an observation post.

previous   next

Sources -
The Battle of Coleford 1643 by Stuart Peachey (1993)
Memorials of the Civil War by Rev. John Webb 1879
The Castles of England, Scotland and Wales, Paul Johnson, Harper & Row, New York, 1989.
The Personalities of the Forest of Dean by Rev. H G Nicholls
Chepstow Bridge before its removal in 1816. A sketch by Mrs Stackhouse Acton.

The contents of this page are from a number of sources, not all completely reliable. Corbet, from whom we have often quoted, was Massey's chaplain, and obviously biased, and a number of the reports from the Reverend John Webb's book are often very one sided, depending on their source.
Should you have any corrections or additions we would gratefully welcome and acknowledge any input.


Dennis Potter   History Magic & Witchcraft Warren James
Family History  HOOF Metal Detectors Witchcraft
Forest Books Local History Mining History Woolaston
Forest War Heroes Lydney Park Tolkien   Woolaston History
  Early FOD Police    County Police History   Blakeney   Ruardean 
Scowles village