Okay, deep breath, this is where the adventuring in 5e begins. You have 6 Missions to get through. Some form natural pairs
- Old Tunnel & Prisoners
- Dragon Attack & The Sally Port
- Save the Mill & Sanctuary
However, you can mix and match as a story telling device.
The PCs will meet the Governor fairly quickly once in the keep. He is on the battlements and this gives obvious opertunities to lauch, Prisoners, Dragon Attack, and Sanctuary from the outset.
The Save the Mill, is a trap for the PCs and needs to be held back until the players have drawn the bad guys attention but again this can be launched by the Govenor.
The Castellan can be used to launch both Old Tunnel and The Sally Point
I choose to offer up the Prisoners, Sanctuary and* Old Tunnel* as a first set of missions and left the teams to do as they pleased. I also choose to spice up the tunnel by setting a simple two gate trap to keep the guys on their toes.
While harrying the players is fun, I again urge you to reward smart rolepay and Ideas. 1 team used their two rogues to persuade an officer that he was needed in the town square then abducted him enroute, while another simple fought a group with a cultists to capture.
Follow that the groups were left with a choice of going on to the chapel or returning to the keep. Which provide a convenient end of session point.