[quote=gcold]
It will take you more than a week to ready up the legion and send them to Skyrim border. I have a new Skyrim player coming in soon, so you need to talk to them before your troops cross over.Also, your horse-riding messengers will arrive in High Rock after 3-4 days, Hammerfell 5-6 days.
[/quote]

That's faster then I thought...and how is it they reach High Rock before Hammerfell? o.0

You literally can't reach the former without going through the latter.