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How could you kill a kraken with medieval technology?
This kraken has a regular squid body/tentacles, but it has some lobster parts too. It has two lobster claws and lots of legs. Also, my kraken has ten huge twenty-foot long snakes coming out along its head.
The kraken is about a thousand (1,000) feet long from the tips of its tentacles to the ends of its snake heads, which extend a bit longer than its head.
This animal is a LOT more dangerous than a whale and a whale could destroy any medieval ship if it was smart enough to attack instead of try and run. From the sounds of your kraken it could tear ships to pieces.
Harpoons are not going to work, this isn't a whale, unless you get a lucky hit this thing outranges your harpooners, harpoons are heavy weapons that can't be thrown very far and your kraken has ten snake heads with the same range and can attack from multiple directions.
Use poisoned bait, fill horse corpses with poison and catapult them in the vicinity of the kraken, or whatever else it has a taste for. Then stay away from it until it's dead.
So, you are supreme ruler and have plenty of resources as well as large and skilled army and navy, and you've decided you want the kraken dead. What is your budget? Various groups of "natives" have hunted whales and other large animals in water for a LONG time, not to mention land. Sure your kraken is massively bigger, so you just need more bodies working on it.
Think about whaling - harpoon the whale, drag around and control with ropes to put it in a position to be slaughtered.
Do this close to shore. Lots of barbed rods, attached to strong but handle-able rope or chain. Get them into said kraken at multiple points all at once, the more the better - row-by harpooning from multiple ships, massive cross bow, whatever you have that can launch. Pass lines to teams of horses, oxen, bewilderbeasts, whatever you have that can pull. Get that sucker beached, add plenty of lamp oil and you can serve calamari bbq style.
Assuming the Kraken will be fought at sea (which it naturally is), then there aren't really much freedom of what weapons to choose from. I tried looking for the strongest weapons in medieval technology and I think there's nothing else stronger than siege weapons.
But what's stopping people from mounting siege weapons to warships? You did not specify a limitation to your question, and the technological advancement isn't that much in the middle-ages. Then why not fight fire with fire if it's the only way?
If your resources permit it, I guess 200+ warships at a safe distance could do it.
I don't know much about ballistics, and I don't know what would be considered as a safe distance since your kraken seems to have very long appendages. I think you should solve that problem next if you see some light from my answer.
...or you could kill it from its insides™ like every movie cliche does. just kidding
First, I must say that killing the squid on the surface of the water is unlikely due to the sheer size of the squid. However, if you repeatedly injure it, it will either die, decide not to bother you, or have to wait to heal before striking again.
Find a cliff facing the sea. Now use boats and ranged weapons to lure the squid over. Now shoot at it from the cliff, attracting it to come as close as possible to the cliff. Now light the fuse and toss the barrel over. Repeat.
Requires some sailors to sacrifice themselves. Load a ship with explosives. Now get the ship as close as possible to the squid, and set it off. Might not kill the kraken, but will injure it.
Go back to the cliff setup, but dump fish into its mouth. Hopefully it keeps its mouth open long enough for you to throw explosives, or whatever you want to throw at it, at it.
Cliff setup, but spiky rocks as well as explosives. These will puncture the creature's skin. A lot.
Use your ships to lure the squid over to the opposing country and their ships. Now it's not your problem anymore.
