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I will have to write a story arc where the main characters will be trapped in a town during a siege. What are the key points I should address / display to make the siege interesting for readers?

They are rebelling against the realm, so they are in the underdog position.

Some things I thought of:

• Food and Water shortage


• Trapped civilians rioting


• Harassment from the besiegers.


• Maybe a disease spreading

But these are just some hooks, not the key elements. Where should I focus?

You have a lot to talk about, in theory. A city under siege could last for months, sometimes a year, without reinforcements (by the way, wikipedia has a nice list of sieges here, both real and fictional).

So, sieges are relatively slow and can have relatively low action (compared to field battles). But you, as a writer, have the possibility of skipping all the "boring" parts: you can portray the anxiety and the tension of the besieged city without letting it drag out indefinetly in your story. In other words, you can describe how your city men becomes tired and exhausted, without exhausting your audience with boredom.

You can do this by interleaving the events of the siege (eg. the attackers trying to get over the wall again, a disease spreading, food supplies being re-rationed) with events relevant to your character arcs (a former nobleman getting impoverished, members of the rioutous city guard becoming local heroes ... depending on who your characters are).

If nothing relevant happens for a long period of time you can show it. The key here that if you have interesting characters, they will be fun to read even in a scene where they are clearly bored. If, on the next day of that scene, nothing new happens and you don't know what to write, you can always skip forward to the next week.

This said, you have a lot of potential sources to draw from, and a lot of theme to cover:

• 
  The external front. Meaning anything related to the attackers: the fight scenes, the siege engine, the sorties, the military and tactics, the ultimatums, the peace talks (eventually) and in general the realm your town is rebelling against.


• 
  The internal front. Everything from the town politics to how the townsfolks are holding out. People can react violently in times of great stress, and your town will act as a miniaturized nation, with limited supplies and manpower. The rebellion will have to hold the morale up to keep the siege on. Guards must be trained, and when they die, someone must fill their shoes. Stict laws must be enforced to ensure safety - watchers must not slack on the walls in case the enemy tries to sneak in at night.


• 
  The utmost-internal front. Talking about a siege doesn't keep you from talking about your characters. Their stories are still important and relevant to the reader, wether you have a single MC or a whole cast, or you consider - as some books do - the whole townsfolk your protagonist.

It's up to you to decide where to focus more, as it's up to you to decide what kind of story you want to tell. Maybe it's about the atrocities of war or the strain that the siege puts on common people. It could even be on how the siege, a ferocious and scary warfare event, slowly turns into routine for the people involved.

The italian novelist Dino Buzzati wrote an entire book (The Tartar Steppe) about a soldier dispatched to a far out fortress, waiting forever an invasion that doesn't come. Your book may also be, as well, a long treatise about routine, boredom, and the feeling of exhausting one's life away.

But coming back to your question, I hope I showed you how there's a lot of interesting stuff to be written in your setting.

Unless there are reinforcements en route, the besieged town may already have lost.

They are surrounded, running low on the essentials. Water might be tainted.

Their fields and herds are feeding the army, the townspeople lacking the time to prepare.

Smaller than a city, it is less likely to have multiple wells within its walls, so water is at a premium.

The characters could wonder if this rebellion is worth the suffering caused by this siege. Might they be able to negotiate fair terms of surrender? If their presence is the only reason the town is besieged, those rioting townsfolk might be coming after them. Divide and conquer might be happening to them.

Will the lives lost should no surrender be possible be worth it? Would they be willing to potentially give their lives to save those of the citizens?

What has the enemy commander been ordered to do? How much leeway will he have? Must the town be razed for having harboured these rebels?

Their hope might be in the overstretched supply lines of the encamped army, but they have few advantages, few options.

Choose if your town will be destroyed, if a massacre will occur and what, if anything, your MCs can do to help. If they are bystanders or lower ranked members of the resistance and potentially unknown to the authorities, they can try and blend in with the civilian population and hope not to be discovered or betrayed.

Perhaps the siege makes them question their methods if not their cause. Les Miserables has the barricade - a handful of idealistic rebels trying to improve the world by defying France and dying. They make their stand and do not leave, though they do wonder if it is worth it all.

Perhaps they disagree

Standing in the bell tower, he watched the unchanging scene. The rich
farmlands, covered by the encamped army led by Demarque. Completely
surrounded. The cries of the hungry, frightened children barely
reached him.

“Low on water, low on food. We cut the rations again - three ounces of
food per adult. People are dying because of us.”

“No, because of them. We did not do this. Those deaths are not ours to
prevent. The King’s army is killing his people. We need to stop them.”

“No, we need to stop this, prevent the next child from dying. They
don’t see the starvation. We do.”

“They know what is happening here and they allow it. Each death is on
Demarque, not on us. We will be remembered, that is our victory and
their defeat.”

“Remembered? How? By whom?”

“
Dismissed.”

His lieutenant lingered before leaving,had a point, but regrets would
do no good. The cause mattered, these deaths could not be in vain.

I suggest reading accounts of real sieges first of all. I read the siege of Lisbon in 1384, written by the chronicler Fernão Lopes, and it gives a vivid image.

The way to portray a siege depends, in my opinion, on the POV: is it a high class person or low class?

Low Class

These are the people who suffer first. If they lived outside the castle and hurried in to save their lives, then they'll be suffering over the lost lands and animals, probably feeling they've just lost years of hard work. They'll enter the town in family groups with a few essentials and will face the hardship of living in the streets.

Once the gates are locked, the food prices will start climbing and the poor people will be the ones to first experience hunger. As the siege continues, hunger will climb up the social ladder.

In 14th century Lisbon, the food shortage was such that people killed all horses, mules and oxen for food, once the pigs and chicken were gone. Children and teenagers would roam the streets in search of rats and birds. Never had the city been so free of vermin! At a certain time, there was a shortage of water even if there was still cereal to make bread with. This led people to bake bread using wine, but the result could only be eaten warm, as it became hard as stone once it had cooled.

For these people, there are only two worries:

1) to not die of hunger and thirst

2) to not die at the hands of the enemy (meaning, the siege must not be successful)

Women and children patrolled the walls alongside the men, pelting the enemy with stones and readying cauldrons of boiling olive oil to pour over anyone who tried climbing the wall. There were accounts of women who donned their husbands' protections (reinforced leather, not armour, as these were lower class) and organised themselves to keep watch. Children would be sent to collect stones from streets and ruined houses for ammunition. Women knew full well their fate would be a little more than just death, not to mention they knew what fate awaited their children. They were up there and were hailed in the text as fierce and unshakeable as any man.

There were cases of plague at the time, so any dead person on the street could start a rumour of plague and spark panic. That meant any dead were quickly disposed of and, should plague really be suspected, they'd throw the body at the enemy camp - if they got the plague, they'd have to abandon the siege, after all.

In this case, the focus must always be two-fold. As much as people suffer hunger and thirst, they will also fear death at the hands of the enemy.

Imagine a scene where a loved one died of a disease related to the hunger. Imagine the family's pain and yet the body being chosen to be thrown over the walls into the enemy's camp. Show the loss, show the anger, show the pain and regret because the loved one will not be properly buried... but even in death, he will still fight the enemy and bring death upon them!

Unless, of course, the people blame the high class controlling the town for the siege. In that case, they may organise a rebellion or work to help the enemies inside, for as long as those rebels and their families are spared. In fact, they may even take matter in their hands, capture the noble people they believe to be at fault and deliver them to the enemy (dead or alive) in exchange for sparing the town.

High Class

The last ones to suffer with hunger. This does not mean they'd be feasting, though. They'd be controlling the food rationing to the utmost, too, but will only feel hunger at a later time.

If they live their responsibility as the town ruler / keeper, they'll suffer for the people's plight - even if only because soon the plight will be everyone's. They will make plans and remake them... because there is nothing to be done but wait and endure. Perhaps a group favours a flash attack during the night, while the others fear those men might be captured or killed, leaving the town even worse for lack of fighters. What if scenarios are checked and rechecked.

The noble person will fear for their family, too. Perhaps some, fearing the worst, are preparing ways to save their wife and children... Maybe negotiate the enemy's entry into town in exchange for the family's life? Maybe offer money? Maybe find a secret place to hide if the castle is taken over? Or perhaps both parents and children rise proudly, ready to die for their beliefs.

At any rate, fear of treason will be high. If the reason for the siege allows for it, priests and spokespeople will rally the people, painting the enemy as baby-eating demons and spurring everyone to destroy anyone who may show an inkling of desire to sell out the town into a slaughterhouse.

Amidst the noble people, there will be suspicions - Who is the least loyal? Who loves their own skin a bit too much to stand strong?

Action scenes are all very well and exciting, but in a siege, the tension is queen. Focus on it. Get inside the skin of those people.

If you want to picture hunger accurately (and are healthy), try eating nothing but a bit of stale bread at meals, alongside a sip of water, for one or two days. Feel how hunger and thirst keep you awake. It'll be easier to imagine how desperate a person would be for anything to eat in a weeks-long hunger, and yet you'll never feel how truly bad it is.

...to make the siege interesting for readers?

A siege is not interesting. It's growing levels of pain and fear until it becomes desperate hope on the edge of hopelessness. It's the will to survive, the strength to endure and the urge to fight to your last breath.

A siege is interesting to us, who are not involved in one, but a real siege is raw emotion: anger, fear, hope, despair. That is what you need to show the readers.

A siege is war, so you should write about war.

I'm not refering to simply write about fights, but rather the silent battle that is tactics. All four points mentioned could be secondary effects of the ongoing siege but it doesn't mean they should be the main point, and it doesn't even mean they should happen: Maybe the besieged town's commander saw through an enemy ploy and prevented a disease from spreading.

In short, write about the war and tactics and how it affects the main characters.

tl dr

Before the siege focus on the planning and preparation that will need to occur. The more information the rebels have about the oncoming army the more they can do to plan their defense. During the siege focus on the efforts to deal with whatever problems are arising in a reactive way.

Before the siege if your rebels know that they will be facing a much stronger force and choose to use the town for their defense you should focus on how they plan their defense.

Do they requisition furniture from civilians to create barriers? Do they try to send out spies to infiltrate the besiegers to learn of their plan of attack? Do they have time to dig new wells to prevent water shortage? Do they gather available foods from homes to a more secure central location?

During the siege you should focus on how the arising problems affect the characters and the rebel strategy.

How do you keep troop morale up after taking significant losses in the initial defense? Is there growing resentment from the civilians that may threaten to sabotage the rebellion? How are the rebels trying to quell that? Are there rebels plotting how they will escape the town if the rebellion goes poorly? If so how do they hide their efforts from the rest of the rebellion to avoid being seen as a traitor?

The only way a seige story works is to put a ticking clock on some aspect of it, something that will force an ending one way or another.

For the people under seige, it can be lack of a specific resource - food, ammunition, oxygen, whatever - and once it's gone they're done, they will be defeated.

For the people at seige a good option is usually that "the cavalry" will arrive at a certain time so they have to break through the defence before that happens otherwise they have failed.

Do both and you have a time imperative on both of them to resolve things quickly.