Spent over an hour with Garmin Tech Support to get my new Garmin Oregon GPS working with MapPoint 2006. ("Rich" stuck with me to figure it out - thanks Rich!)
Here was the method that worked:

1. Installed the Garmin Automatic Updater software. This then updated my GPS from version 2.20 to 2.60, which loaded automatically after I restarted the GPS.

2. I downloaded the "USB Driver" file and the "Spanner" file from the Garmin website and ran them. The Spanner file is available from the Garmin website under Products/OEM/GPS 18 (You may get a warning about using Spanner with the wrong GPS, which you can ignore since it is the same program for all). Once you have installed Spanner you can run it from your Start/Programs Folder

4. The USB driver is available under "Downloads" on the website.

5. So, here are the key factors in using the Oregon GPS with various types of mapping software:

  • To run the GPS with Garmin MapSource North America maps the GPS Setup/System/Interface must be set to “NMEA In/Out”. That is usually the default setting on the Oregon GPS.

  • To run the GPS with Microsoft MapPoint 2006 or Microsoft Streets & Trips 2006 you need to change the default settings and use the following procedure :
    • On the GPS set the Setup/System/Interface to “Garmin Spanner”.
    • Run the “Spanner” program you have installed on your computer
    • Plug the GPS into your computer USB port and follow instructions when the "Found New Hardware Wizard" pops up on your computer.
    • Select “No” on the GPS when it asks if you want to go to Mass Storage.
    • Open MapPoint 2006 or Streets & Trips 2006 on the computer
    • Click on Tools/GPS Task Pane/ ConfigureGPS/Scan on MapPoint 2006 or Streets & Trips 2006 (at this point the program should tell you it recognizes the GPS)
    • Click "Start GPS Tracking" (Your current location should now show up on the MapPoint or Streets & Trips map as a red circle.)