A deductible must pay on each loss to which the deductible applies.

The deductible needs to be paid when your coverages, usually comprehensive or collision, are covering a loss. So if you have multiple incidents in one year that has you placing multiple claims through your insurance policies you will need to pay multiple deducible amounts.

In your case since the damages are from two separate incidents with damages to your vehicle in different areas then 2 different claims would need to be made. It sounds as if the damage from the park and ride would be due to a hit and run and fall under your collision coverage. The damage from the camping trip may be a comprehensive claim, depending upon how the damages were sustained.

If the new damages were in the same area as the previous damages then you may have had your claim reduced by the cost of the pre-existing damages that you chose to not repair. That is one reason why it is important to repair damages to your vehicle so that future claims will not deduct pre-existing damage.