Battle of Upton The Battle of Upton was fought on 28 August 1651 when a New Model Army detachment under the command of Colonel John Lambert made a surprised attack on Royalists defending the river Severn crossing at Upton - Upon - Severn , below Worcester . In the action which followed the Royalist commander Major General Edward Massey was severely wounded and the surviving Royalists were driven out of the town and north along the Worcester Road . The successful attack allowed Parliamentary forces to approach Worcester from the west and was an important action in completing Cromwell ' s investment of Worcester as a prelude to his assault and capture of the city . Prelude . On his return from Scotland Cromwell took command of the Parliamentary forces arrayed against the Royalist army encamped in and around Worcester . Initially he concentrated his forces at Evesham which blocked any Royalist advance on London . Cromwell ' s force at Evesham were increasing daily . By the time he arrived in person on 27 August his forces out - numbered the Royalists by nearly two to one and he was able to carry out the second part of his plan , which was to cut off the Royalists from Wales and the west . His first planned act was to occupy the west bank of the Severn . To do this , on the next day , 28 August , a strong detachment , both horse ( cavalry ) and foot ( infantry ) , under the command of Colonel John Lambert , was ordered to march from Eveshann to Upton - Upon - Severn , drive Major General Edward Massey from there , by taking possession of the bridge and occupy the town ( which is located on the west bank of the Severn ) . Leaving Evesham , Lambert detachment marched the , arriving on the east bank of the Severn at Upton that the evening they found the bridge broken down , but a plank had been left across the ruined arches by which it was possible that few daring men might , with some danger and difficulty , effect a passage and surprise the Royalists encamped on the West bank in the town . Lambert resolved to try . Massey was quartered in the village of Hanley Castle , at Severn End , a house of the Lechmeres , about a mile away , on the Worcester Road ; his men were billeted in the town . Some slight earthworks had been thrown up between the town and the brook on the Worcester Road , which formed a strong position to resist any advance made along the road . Lambert saw that if the Upton was defended it would be impossible to carry it in its then state . There was just one chance : the Royalists might keep a bad look - out , as no sentries were posted , possibly they had no idea any enemy was near . To cross the river was a service of difficulty and danger , but unless the river was crossed the plan laid down could not proceed . Lambert , therefore , determined to take the risk . Battle . During the night he kept his men out of sight at Ryall , so as to raise no suspicion or alarm . At daybreak , selecting 18 picked men out of his force , he ordered them to cross the bridge , and , as soon as they had done so , to seek some shelter in Upton , so as to be able to hold the bridgehead until they were reinforced . On 29 August , in the grey morning light , as dawn was breaking , the 18 started on their mission . Never were troops given a harder task than Lambert ' s men were now called upon to perform . In dim daylight to walk in single file over a long , narrow plank , high above a deep , rapid river , with the prospect each moment of being fired upon , was a task before which the bravest might quail . It is no disgrace to Lambert ' s men to say they did not like it ; yet they did not shrink ; they knew that at all hazards the river must be crossed , and that they had to cross it . When they got on to the plank , and began to march in single file , they could not stand the running water below them ; their heads swam , and they were in danger of falling . So they sat down on the plank , straddling across it , scrambling along . After some delay all reached the Upton bank in safety . There some hot work awaited them . As they formed up the Royalists perceived that they had crossed the river and at once attacked them fiercely . Carrying out their orders Lambert ' s men retreated , first into the churchyard , then , finding that their numbers were too few to enable them to defend it with success , into the church itself , fastened the door , and fired through the windows on the Royalists . The attack was determined . The Royalists pushed on up to the church , but , unable to effect an entrance , set fire to the building , and shot at the survivors of the 18 through the windows , trying to thrust them with their pikes , or cut them down with their swords . The survivors held out bravely , returned their assailants ' fire , causing them some loss . Massey , awoken by the sound of the firing , at once set off to his men and directed the attack on the church . All of the 18 were , to all appearances , doomed . Over the bridge , with the Royalists now on the alert , no passage over the bridge was possible . Under the fire that would be poured on it no one would live to walk the plank . Lambert was loth to leave his men without an effort to save them . The river was low , the tide was out . It was said to be fordable , but that the ford was difficult and dangerous , but possible . Lambert decided it should be risked . At the spot below the bridge , known now as Fisher ' s Row , where the ford was said to be , Lambert ordered his dragoons to enter the river , get through at all risks , and relieve the men in the church . The dragoons entered the river ; floundering about , partly fording , partly swimming , in some way they got through . Forming up on the Upton bank , they charged on the rear of the Royalists , who were attacking the church . Surprised at this unexpected and sudden charge , the Royalists at first gave way , but , recovering from their surprise , rallied , and in their turn charged the dragoons , drove them back , killing several men , and many horses . But Lambert , having found that it was possible to ford the river , did not leave his men unsupported ; he sent more horse across , so the Royalists rapidly became out - numbered . Fighting fiercely , they were only driven away from the church by Lambert ' s superior numbers ; but they were driven back , and such of the 18 as remained were rescued . Not satisfied with the rescue , Lambert resolved to complete his work . The Rolalists retired into their entrenchments ; they were to be driven out , Lambert ordered the entrenchments to be stormed . Again the fight was sharp . The Roylists , now on the defensive , fought well , and had the fight been on anything like equal terms Lambert would have failed to carry the works ; but to the Roylists no reinforcements could come , while the assailants were constantly increasing in number . Planks had been placed over the arches , the troops could now pass easily over the bridge into Upton . Massey already had had a horse shot under him , now fell sorely wounded . Discouraged by the loss of their leader , the increasing number of the enemy , their continuous and sustained attacks , the 300 Roylists at last gave way . Lambert ' s men carried the earthworks , the Royalists , abandoning camp , baggage , and wounded , made off as fast as possible along the Worcester Road . It has been said that the rout was so complete that each horseman took up a footman behind him so that they might make off with greater rapidity . But this can hardly be true . Not only were very few prisoners taken by Lambert ' s horse , but Massey got back safely to Worcester . He was so badly wounded in his head and thigh that he could not sit on his horse without support , and could not suffer his horse go out of a walk . Aftermath . The Upton fight had been sharp while it lasted . Lambert deserved his success by the bold way he executed his orders and the tenacious grip by which he held on to Upton when once he got a foothold there . In the opinion of the historian J . W . Willis - Bund in all the Worcestershire fighting in the Civil War no braver act is recorded than that of the 18 who crossed the bridge , held the burning church against 300 Royalists , and enabled Lambert to win his victory . But neither its severity , nor its duration , nor the bravery of Lambert ' s troops , mark the real importance of the Upton fight . It enabled the turning movement , cutting off the Royalists from Wales and the west , to be carried out . It was also the first step towards driving in and crushing the right wing of the Royalist , enabling the encircling movement to be begin , and the elaborate defences around Worcester which the Scots had taken such pains to construct to be turned . How important Cromwell regarded it is shown by the fact that later in the day he came himself to Upton to thank Lambert ' s men for their courageous behaviour , and to see the best use was made of their triumph . Cromwell ordered the bridge at once to be repaired and made passable for troops . Cromwell , the same day , sent his second in command ( General Charles Fleetwood ) to take the command at Upton , ordering him at once to march there with a large force of troops , the whole of Colonels Lambert and Deane ' s brigades . In pursuance of these orders in the course of the next day a Parliamentary force some 12 , 000 strong was encamped on the west bank of the Severn , Its outposts were pushed forward to the Old Hills and nearly to Powick . Its vedette s were sent up the Teme valley to cut off all attempts the Royalists might make to communicate with Wales or the west .