Battle of QuebecQuebec was one of the most readily defended cities in North America. Its “lower town” was built on a narrow terrace between a high cliff and the wide St. Lawrence. Its “upper town” was perched at the top of the cliff and surrounded by 25-foot thick stone walls. A narrow winding road connected the two parts of the city.
An American army camped on the outskirts of the city in early December. Its commanders were Brigadier-General Richard Montgomery and Colonel Benedict Arnold. Somehow these men had to take Quebec if they were to complete the conquest of Canada. They also knew that the attack would have to be made quickly because many of the men’s enlistments would expire at the end of the month. Somehow also, the attack would have to succeed despite the fact that the British defenders outnumbered the attackers by a fair margin (the Americans had about 1,000 men; the British, led by Governor Guy Carleton, had around 1,800).
The Americans tried a variety of stratagems: they tried bluffing the garrison into surrendering, luring the garrison from the city walls, and wearing the garrison down by bombardment and sniper fire. When these efforts failed, they mounted a predawn assault, in a snowstorm, on December 31.
Montgomery wanted to deceive the British as to where the assault would be made. In advance he had hundreds of scaling ladders constructed, so as to convince the British that a frontal assault was planned. On the morning of the attack, John Brown’s provincials and James Livingston’s 1st Canadian regiment feinted against the city wall, so as to hold the attention of the garrison.
Montgomery’s main attack was made against Quebec’s lower town. To maximize the possibility of success, both ends of the lower town were to be assaulted at the same time. Montgomery led a column of New York Continentals from the west, while Arnold led a mixed force from the east (specifically, Continentals from New England, riflemen from Virginia and Pennsylvania, and Lamb’s New York artillery company). Lanterns were set up to light the assembly points, and signal rockets were used to coordinate the attacks.
Despite these careful preparations, the attack was a fiasco.
The British were not deceived by the feints against the city walls.
At the western entrance to the lower town, Montgomery’s column encountered a two-storey blockhouse armed with four cannon. Despite a stealthy advance, the vanguard was detected and annihilated. Montgomery was struck in the head and killed instantly; 12 others died around him. The wet weather made it difficult to operate firearms, and the rest of the column, horrified by the death of their commander and facing what appeared to be an insurmountable barrier, decided to retreat.
Arnold’s column was first observed as it passed under the city walls en route to the east end of the lower town. Arnold was hit in the ankle while leading the column, but the men pressed on without him. The barrier they faced was not as formidable as the one confronting Montgomery’s men. Here, two cannon had been placed on an elevated platform. A wall in front blocked the street. Once the cannons fired, the Americans rushed forward with scaling ladders, mounted the platform, and captured the defenders. (In the lead was one Captain Daniel Morgan of Virginia, who would end the war a brigadier-general and an American hero).
By the time the Americans had reorganized on the far side of this barrier, British reinforcements from the upper town had taken up positions at a second street barrier and in the buildings around it. The Americans became pinned down trying to force this point. Worse, some of the British retook the first barrier and cut off their escape. Many of these men were killed and more than 400 captured.
Afterwards, the remnants of the American army maintained a grim blockade of the city. Some reinforcements would arrive that winter and spring, but any real hope of taking Quebec was gone.
Some passages by participants
Captain Thomas Ainslie (British militia) on the feint attack:
“About 4 o clock in the Morning Capt: Malcom Fraser of the Royal Emigrants being on his rounds, saw many flashes of fire without hearing any reports; the sentries inform 'd him that they had perceived them for some time on the heights of Abraham, the sentinels between Port Louis & Cape Diamond had seen fix'd lights like lamps in a street--these appearances being very uncommon & the night favouring the designs of the enemy, Capt: Fraser order 'd the Guards and Pickets on the ramparts to stand to their arms. The drums beat, the bells rang the alarm, & in a few minutes the whole Garrison was under arms--even old men of seventy were forward to oppose the attackers.
“Two Rockets sent by the enemy from the foot of Cape Diamond were immediately followed by a heavy & hot fire from a body of men posted behind a rising ground within eighty yards of the wall, at Cape Diamond, the flashes from their muskets made their heads visible--their bodies were cover 'd: we briskly returned the fire directed by theirs--at this moment a body of men supposed to be Canadians appear 'd in St Johns suburbs,--& the enemy threw shells into town from St Roc.” 
Lieutenant-Colonel Henry Caldwell (British militia) on the repulse of Montgomery’s attack:
“In the mean time, Montgomery made his attack at Près-de-Ville… He got past some pickets… but the post was much stronger than, I believe, he imagined, and defended by four cannons there and a 4-pounder; they were served by some seamen under the orders of the master of the transport; his name was Barnsfare. The guard was under the command of a Canadian officer of Militia; the men, Canadians and British, mixed, Barnsfare declared he would not fire till he was sure of doing execution, and with the utmost coolness, waited till the enemy came within his view, at about 30 yards distance, where they received a general discharge from the cannon and musketry. Nothing but groans were heard, and the rebels immediately retired…” 
Private Abner Stocking (American Continental) on Arnold’s attack:
“[Arnold] led the forlorn hope in person, and was followed by Captain Lamb with his company of artillery, and a field piece mounted on a sled. Close in the rear of the artillery was the main body, in front of which was Morgan’s company of riflemen… In this order Arnold advanced with the utmost intrepidity… against the battery. The alarm was immediately given, and the fire on his flank commenced [i.e., plunging fire from the walls of the upper town], which, however, did not prove very destructive. As he approached the barrier [to the lower town] he received a musket ball in the leg which shattered the bone, and he was carried off the field to the hospital. Morgan rushed forward to the battery at the head of his company, and received from one of the [cannon] pieces, almost at its mouth, a discharge of grape shot which killed only one man. A few rifles were immediately fired into the embrasures, by which a British soldier was wounded in the head, and the barricade being instantly mounted with the aid of ladders… the battery was deserted without discharging the other gun. The captain of the guard, with the greater number of his men, fell into the hands of the Americans…”
“We had now passed the first barrier; but a second we knew was before us and not far distant. We had no pilot and the night was very dark and dismal. We took shelter from the fury of the storm under the sides of some of the buildings and waited for day light to direct us. At the dawn of day we collected in a body, seized the ladders and were proceeding to the second barrier, when we were hailed by a Captain Anderson [British] who had just issued from the gate with a body of troops to attack us. Captain Morgan who led our little band… answered the British captain by a ball through his head, his soldiers drew him within the barricade and closed the gate; a tremendous fire from the windows of the buildings and port holes of the wall, was directed against our little host.”
“Thirty of our privates being killed and thirty five wounded, and surrounded as we were on all sides without any hope of relief, we were obliged to surrender ourselves prisoners of war.”