You likely made one or both of the following mistakes.

1.When creating the route, in most cases you only want two "destinations" the start point and the end point; everything in between should be way-points.
(If you use multiple destinations, when you export it from the planner and import it to the bike, it creates a ride with multiple parts, which is a PITA).
In the diagram, Jack-and-Jill hill is a Waypoint. To see Waypoints, you will need to flip the toggle.


2. When importing the ride, via USB or through the phone, to the bike (or when you choose the route to ride on the Boom.. I don't recall when you are given the option) be sure to choose the options "Select All" (I don't recall the exact wording, you will recognize it).
Otherwise, it only gives you what you selected, and most of the time, you want the entire ride. (I tend to use the USB).

After doing it this way a few times, you may want to experiment with adding a 3rd destination in the middle, e.g., where you will have lunch.
When doing multi day rides, I create 1 route per day.. the routing app gets very sluggish after adding about 12 waypoints.

One thing (I call it a bug) is that the router app and the H-D nav system use different algorithms for mapping the the route between waypoints. The Boom 6.5 seemed to prefer shorter routes than the planner, the GTS seems to prefer going out of the way to find a highway (if it is not too far out of the way) than the planner.

 

One minor pro tip. Zoom in closely on your “in progress” Ride Planner map as you are plotting it, because as you will see, it is dodgy as hell if you don’t place your cursor EXACTLY on the point on the road or intersection you want it. The program is busy trying to do what IT wants to do, so it’s like wrestling a snake that’s trying escape your grip the whole time.

 

I did that and clicked on the other carriage way on a road. I didn't notice it right a way but the route became interesting as it took me down a couple of roads and round in a circle.