Can you record multiple rides on a Garmin 500 and then download them sequentially onto Strava?
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Can you record multiple rides on Garmin 500
Yes you can record as many rides as there is room on the internal memory. Once you have completed a ride hit stop, then hold the lap/reset button for 3 seconds to get the unit to save the ride and reset the screen. This will save the ride as a .fit file on the unit (Figure 1).
The Garmin 500 is an older unit with less memory, but right now I have 124 rides on my Garmin 500 dating back to Nov 2018 and there is still plenty of room left.
then download them sequencially onto strava
You will need to connect the Garmin unit to a compatible computer using the supplied USB cable, it will typically mount as an external drive (Figure 1). From there you can manually upload the .fit files to Strava using their file upload feature.
Alternatively you can install Garmin Express on your computer, which will automatically upload the .fit files to Garmin Connect when you connect the your Garmin 500 to your computer. Strava can then be set up to connect and download activities from Garmin Connect.
Personally, I just do it old school (file upload).
I googled your exact question as written and the top match is
After your first upload, Garmin will also sync your past 90 days of activity to Strava.
Remember garmin devices aren't cell phones, the current models depend on either a computer connection (via USB) or a cellphone (via bluetooth) to push your data to Garmin Connect.
From there the Strava integration is a "third party app"  and has to be authorised to connect with Garmin Connect. Once this is done, 90 days of your Garmin Connect records will be pushed to Strava.