This trip will be mainly road, but I will be investigating some other routes for a (Potential) fatbiking trip. I generally hear that most offroad routes can be difficult to unpassable on a bike though.
Bag – Yes was planning a a light synthetic bag case it turns really wet. Merino base & down jacket for insulation when needed.
Hat – Waterpoof craghoppers hat & taking waterproof glove in addition to the lighter cycling ones.
Will be riding flat pedals with boots (My normal setup)