Just trying to get an idea for life during the long months of a siege.
Obviously once food starts getting low and people start getting desperate things change but to start with, is life relatively normal?
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The following answer mostly applies for 14th and 15th century western warfare ;-)
It must first be understood that medieval cities were not "whole". The total control of a medieval town required a lot of conniving and plot. The bigger the city, the more factions it had. A "standard" town would have at least two seats of power: the bishopric and the city hall. A representative of the king, like the 'bailly' in France could be another player. Whoever wished to take Paris had to get the university on their side, too.
I observed that when Amiens was taken back by the Burgundians in 1436 (read Monstrelet's Chronicle), the 'city' (where the bishop ruled) was left untouched. Rebels from the 'town' (under the jurisdiction of the city hall and the guilds) actually tried to take refuge with the bishop but he simply sent them on their way and the new bailly took over unchallenged.
Those type of situations gave way to funny happenstances. A medieval town could be taken and re-taken in a very short amount of time if leaders of opposite factions were living in the same city. More funny were the cases of city defenders having lost their town but who kept the control of one or two towers among the city walls.
When the crusaders took Antioch during the first crusade they found themselves in a very difficult situation. They had gained control of the city but not of the fortress. However, a new army was coming to reinforce the defending army. The crusaders were therefore besieged within the city they had just taken yet didn't totally control. We can find many examples of the like in later centuries.
Besieging a city was a very expensive and risky venture. Elite knights and men-at-arms were few. Most battles were fought among a few hundreds of "soldiers". How can you take over a city where several thousands can show up to defend the walls? You needed to rally the 'communes' or the 'common people' so to speak to manage an effective siege. Then you'd get along the tens of thousands of men on the battlefield. Commoners lacked the knightly culture though and they were quite unpredictable. That's why most cities were taken by surprise thanks to some commando type of missions.
Since medieval towns had rivaling political players within their walls, a big part of taking a city over was to seduce those party leaders and grant them satisfaction. Jean de Villiers de l'Isle-Adam, who managed to take Paris not only once, but twice, first in 1418 then back in 1436, only achieved it because he was good friend with the butcher guild and the university. When Joan of Arc attacked the city in September 1429, there was no friends within the walls to help take over the capital.
Another problem was that towns were very difficult to surround properly. Even when he arrived with something like twenty thousand flemish militia to attack Calais in 1436, Philip the Good couldn't strangle the city completely. The people of Calais were still going out with their cattle, for example, which gave way to epic or ridiculours skirmishes. It is very rare that we find a siege like the one of Melun, in 1420, when the French starved so close to death that they had to kill and eat their own horses.
The question arises: why take a city when you can plunder the countryside? Well, for one, there might be castles and garisoned troops all over the place to prevent such acts of aggression. Jean de Luxembourg, lord of Beaurevoir, had such a system in place to defend the Eastern part of Picardy. However he was a well-respected, renowned and mostly feared overlord with close connections to the Burgundian court. Once the political chessboard was overturned, though, even the Duke of Burgundy thought twice and eventually didn't risk to mount an army against him. The king did, but that's another story. (Jean de Luxembourg died before the king's army reached his lands and his heir and nephew settled the matter by acknowledging the king's authority.)
Most of the territory wasn't safeguarded by some Jean de Luxembourg, though. It was quite easy to tear the countryside apart. The English did it several times during the first half of the Hundred Years' War. They would do it to provoke the French into an open-field battle. Crécy (1346) and Poitiers (1356) were the results of such provocations. Charles V said no more and chose for a war of attrition: no more open-field battles, only skirmishes and surprise city take-overs. It really changed the face of the war.
Pillaging and plundering a countryside was nevertheless a fine way to bring a city to its knees. Medieval cities were directly co-dependant from their neighbouring countryside. If an army were to threaten it then a city would easily pay up in order to safeguard it. Sure, the city was well-defended enough that it couldn't be taken. But could the citizens chase away a company of men-at-arms without a proper company of their own sent over by their lord? They couldn't.
Though city-dwellers were "free men and women" they still had to accomplish many tasks. One of them was the town-watch. It was up to city-dwellers to make the rounds on the walls, to break the ice of the moat around the city (to make sure no one would cross it and make their way to the walls too easily--which happened!), etc. They had to provide material support in times of war, women too, by bringing water, boiling oil, and many other things to the "frontline".
The roads were guarded by "boulevards", or road-block fortifications, and they prevented enemy troops to get too close from a city. Besieging a city therefore often began miles away from the city walls. It guaranteed the safekeeping of pastures, agricultural fields and suburbs around the town. Such boulevards had to be built by city-dwellers themselves. Even besieged, a city could keep some kind of normal life unless the situation became too dire. Since a city was not often properly surrounded, exterior communication was not so difficult and food could easily be brought in.
Some people speculated and made a fortune during times of war by raising the price on crops, for example. It was a criminal offense but many got away with it... Money often became an issue for besieged populations and they hoped to rely on the church or their lord to get by. Having a rich protector, serving in a mighty house, was certainly a way to stay on safe side of things. Anyway, it took quite some time for the situation to be really desperate unless the enemy army was actually overwhelming.
If a city was besieged and couldn't be taken over "Rambo style" with a clever, daring an deceitful tactic, it would first open on several weeks of skirmishes around the boulevards and the countryside. Nearby smaller towns would also serve as battlefields. People often found refuge in stone built churches: they were torn apart or put on fire.
Delay was the key words for the defenders. The name of the game was to hold as long as possible for ally troops to find their way to the siege and help. Montargis waited and waited until La Hire arrived and saved the day, in 1427. It is an interesting case, however, because La Hire and his friends wouldn't help Montargis unless they got paid. Indeed, if besieging a city was a most expensive affair, so was defending it!
Larger cities would hold much longer. They often had pastures and fields within their walls that belonged to this or that abbey. You'd have cattle within the city walls too: cow, pigs, sheep... Not enough to feed the entire population for a prolonged time, but just enough to help the city hold against the enemy.
Renowned knights would then square things off in many skirmishes until one or the other party gathered enough money to push the siege forward or to break it off. Journals and chronicles of the time often mention who fought bravely during the first hours/days/weeks of a siege.
The surrender would always come into the form of a peace treaty between the military leaders of both parties. Often the defender would ask for his people to get a safe-passage accross the enemy territory to get back to an allied city. The military leader of a city was not always taking the city-dwellers into consideration, or just couldn't protect them, and more often than not he allowed his enemy to pillage and plunder the taken city. That's why, among so many other reasons, city-dwellers didn't have men-at-arms to heart and often mistrusted them. There are cases of city-dwellers that actually denied entry to supposedly allied men-at-arms when the countryside was torn apart by roaming rogue companies. Hell, the Duke of Burgundy found himself trapped inside the city of Brugge and had to fight his way out!
Don't hesitate if you have a follow-up question on the matter :-)
Edit: I'll be cooking, eating, walking my dog, etc. (You know, some basic quarantined life...) Don't worry though, I'm getting to your follow up questions whenever I can! They're very interesting and make up for great write ups! Please avoid redundancies and make sure your question hasn't be asked before ;-)
Edit: Thank you all for your interest in my answer and your very interesting follow up questions but I'd like to close this thread if you don't mind, life must go on and all :-) If I haven't guaranteed that I'd come back to you sooner or later by now I won't be answering your follow up questions. The AskHistorians subreddit remains at your disposal though and it has many experts that can help you getting the knowledge you seek! See you soon <3
There is very little written about the lives of average people in the period I study (10th century Holy Roman Empire). The main source for this period is Flodoard of Reims, whose descriptions are quite sparse and rarely focus on much beyond broad strokes. But I'll give a few highlights from his annals that might help you extrapolate.
In the early 900s, there was rising sentiment against Charles the Simple. In 922, Charles and count Robert were setting up their opposing armies in the vicinity of Reims. Robert attacked about 200 people who had set out to plunder Reims. Charles then sat his army for three days about a league away from the city, but civilians from Reims kept capturing his horses. So Charles attacked "even though it was Pentecost Sunday" (June 9). There's no mention of a protracted seige. To the contrary, Charles withdraws and Robert is declared the king of Reims in July.
In 923, Charles kills Robert at Soissons in a surprise attack, and Charles seized spoils especially from the rusticani (rustics, aka country people) and the people leaving the suburbs.
Raoul replaces Richard as king. Raoul sends Bishop Wigeric of Metz to recapture Saverne, but ends up there for the entire autumn because the garrison holds out. Eventually, no aid comes, and Raoul received unnamed hostages, and Wigeric destroys Saverne. Meanwhile, king Henry of Germany crossed the Rhine and carried off a bunch of plow animals and youths.
In 925, Ragenoldus heads off to beseige the castle of Noyon. He lights the suburbs on fire to persuade the garrison to come out. Which they do, and together with the inhabitants of the suburbs, the garrison drives him out.
In 931, Raoul sieges Reims. After three weeks, the civilians open the city to him.
Back in Noyon, in 932, after the Biship dies, one of the city's clerics let Count Adelelmus climb the walls. The count "collected" some men from the suburbs and attacked the city, but the people in the walls counterattacked and drove him out. Adelelmus fled into a church, but he was killed next to the altar, and the civilians (cives) retook Noyon.
So while I don't have any accounts of the specifics of normal life during a 10th century seige, since the chroniclers rarely bother to mention them (very few normal folks are written about in this time period, unless they become saints), you can see that townsfolk didn't just sit on their hands while soldiers did war. They actively engaged in hostilities when their cities were threatened. People would have to prepare for that. And since cities, villages, suburbs and churches were routinely plundered, it would be logical that people who didn't manage to escape in advance of the approaching army would also be trying to hide their goods.
Follow up question if this is allowed? I was under the impression that all non-essential personnel (such as a peasant) would be kicked out of the castle prior to any siege to make supplies last longer? Could someone shed some light on this as well?