Right, I've done some calculating, and as it starts at 17th, I've taken the Dragonborn's journey from Helgen to the beginning of our journey to take roughly 2 months and a day. This takes us to the 15th of Frostfall, on a cosy Middas morning. I've made a wee calender, so every time there's a timeskip, I'll be putting up the new date with my posts.
Also, if you want your character to air some opinions, but not actually voicing them to the other characters, or even perhaps foreshadowing a plot you're interested in leading, I'd recommend doing little journal entries. It's not uncommon for adventurer's to have journals, so it could be interesting, especially if you want some character development.