@tigertrader
From the Garmin wiki:

Follow these steps to simulate driving a route from A to B (you can skip steps 2 and 3 if you want to simulate a route from your current position):

1. Put the Oregon in demo mode (Setup>System>GPS>Demo Mode)
2. Select WhereTo?, pick your starting location like a waypoint, POI, etc., and press "Go". Call this point A.
3. Select "Move to Location" when asked if you want to simulate driving this route.
4. Select WhereTo? again, pick your destination location and press "Go". Call this point B.
5. Select "Yes" when asked if you want to simulate driving this route and the Oregon will simulate following the route from A to B.

Note: Depending on your location and the maps you have loaded you may get an error after step 2) indicating a "Route Calculation Error". If so, you can put the unit in Off road routing mode (Setup>Routing>Guidance Method>Off Road) prior to step 2) and back to On road routing mode after step 2) (Setup>Routing>Guidance Method>On Road For Time) to avoid the issue.

If you still can't get it to work, please PM me and i'll move these Oregon specific posts to a new thread. This is quite OT in here.