While it is possible to sync your calendars and contacts from outlook to the ipad (via iTunes), I recommend using an online account instead. Sync your Outlook to a service like Google, and then do the same with the iPad.
The advantages are that you have a backup of your stuff on the internet, that you can acess with any computer. If your computer and/or iPad should bite the dust, any new device can be simple set up with the account again, instead for trying ot import/export/sync the lost contacts. Because the were never lost. Also the contacts and calendars will update on each computer/device whenever you have an internet connection, instead of having to wait until you manualy sync them together.
I know it is possible to sync Google with Outlook, but I don't know the procedure. I'm sure it can be found somewhere on the Google help pages.
To set up your iPad you'll wan to use the Exchange settings instead of the GMail ones, so that you can sync contacts and multiple calendars.
Here are the isntructions if you decide to take my advice.
Setting up Google Sync with your iOS device : Mail, Calendar, & Contacts - Google Mobile Help
If you want to use iTunes, the settings you need are in the Info tab. You'll see this only when your iPad is connected to iTuens and selected under the Devices list.
Whatever you do, do not use both the manual syncing in the info tab and internet account syncing at the same time. It will cause problems.