Originally Posted by Red Brooklyn
Man, it's been too long. How do we know Davos is meeting up with Rickon? I only have a vague recollection.
In book 5, Davos goes to Lord Manderly who was a Stark bannerman to try to get his support for Stannis now that Robb is dead (and Bran and Rickon are still thought to have been killed by Theon). Lord Manderly has a bunch of evil Freys in his court and is publicly siding with the Lannisters as a turncoat like the Freys and Boltons. Manderly tells Davos in front of the Freys that he is dead, then puts a fake Davos head on a spike for all to see, thus everyone thinks Davos is dead and Manderly is now on the side of the Lannisters and Freys and Boltons.
But Manderly secretly tells Davos that Wex (a mute servant boy from Winterfell) survived the Winterfell massacre and saw Bran head north and Rickon head wherever he went, so Wex followed Rickon and then reported to Manderly. Manderly tells Dsavos that if Stannis saves Rickon, he can unite the North behind a surviving male Stark to defeat the Lannister/Freys who all loyal Stark loving northmen really hate. He sends Davos off with a ship to go find and bring back Rickon. That's all we know at this point.
The book does not say where Rickon is, but in typical GRRM fashion he included some subtle hints that seem to indicate he and Osha went to the island of Skagos (which is supposedly a very wild place with strange creatures and people which fits in with all the "wild" that surrounds Rickon). Skagos is off the far northeastern coast of Westeros near the Wall. For those interested, here is a link to a cool map of Westeros I saw recently on another site.