To clarify: it shows tracklogs + photos from participants that use MRA Navigation to drive the routes you upload.
I don't think the timeline can be used to add details ahead of the trip. Instead I would recommend:
adding those details to the routes themselves
give the routes names that include the date, as well as the start and end towns, they should be easy enough to find, for example 0617 (Tue) Rosslare - Cork for a trip on Tuesday, June 17, from Rosslare to Cork.
By putting the month first, you can sort the routes by name to get them in chronological order.