I just ran across the Windows Live Local Add-in for Outlook (beta).
This add-in enables you to add maps and directions to your Outlook meeting requests, does time calculations for travel between your start location and your appointment locations, can adjust meeting departure time based on the estimated travel time, store custom locations, and print the map and step-by-step driving directions to take with you on the road.
It works in Outlook 2002 and 2003, US English versions only at the moment. Once installed:
- Start Outlook.
- In Calendar, create a new appointment or meeting request.
- Click on the Location tab to specify your appointment location. From there, you can calculate a route, get directions and add estimated travel time to your start time.