The easy way that gives you the most power is probably to buy a program to keep a Google Calendar synced with your Outlook calendar. This way you get the benefit of the two-way syncing, as you update google calendar, it should update your Outlook calendar.
Another way we just added, and we are offering it out for you to use - as-is and without support - is subscribing to an ICS calendar in Outlook.
Here I'll show you how to do it in a modern Outlook 2013 that is already connected to a few Exchange calendars.
First, head to your field jobs page and copy the link.
Then go to Outlook, Calendars, and Open Calendar from Internet
All set! Your entries for 60 days prior and 60 days in the future will show up on the calendar.
*Note - this ICS link only updates every 30 minutes, so if you are testing this - be aware of that.