Is the problem one file containing 2 rides? Or you uploaded 2 files (one for each ride) and want to be able to select/filter what Garmin reports to tell the difference? See Looigi's suggestions for the 1st problem. For the second, you can edit the type of activity in Garmin Connect. The system has multiple categories for rides - road, trail, indoorl; and can further identify them as transportation, training, race, other events,... I usually do this immediately after uploading ride files while I still remember what I was doing/trying to do. You can export the ride data to a spreadsheet to perform further analysis, or to add criteria you logged separately from the data in Garmin.