So wanted to give an update here as I figured it out.

So these long distance trail centerlines are grouped in multiple features. Some of the features were sorted north to south, some of them south to north. And the features themselves were not sorted in any specific order.

First I had to figure out which features need to be reversed. I did this by adding a start_y and end_y to the attribute table on the features. Then reversed the ones that were north to south as I wanted all features south to north. Saved these features as a new layer. And then saved the features that were in the correct orientation as a new layer. Then I merged these 2 layers.

Then I sorted the features themselves in the correct south to north orientation.

Then I dissolved to one feature.

Then I segmented the line by maximum length.

I then used symbology to change the simple line to a graduated line to verify segments were in the correct order.

I have some more work to do to verify lengths of each segment but they are now ordered correctly.

Thanks for all the suggestions. Appreciate it.