When buying my mountain home, I noted the rough entry from the highway and thought to fix it.
The years-long process that ensued went something like this:

1. Fill the holes with rocks until the holes are somewhat level and stable.
2. Wait for the next rain.
3. Watch out for on-coming traffic and use hands and snow shovel to remove rocks from highway.
4. Fill holes with bigger rocks.
5. Wait for next bigger rain.
6. Relocate rocks to refill holes.
7. Reach out to landscaper who provides phone number for excavator.
8. Contact excavator who explains that the Virginia Department of Transportation (VDOT) handles driveway entry repairs.
9. Wait for next bigger rain.
   
   
   
   
10. Fill worst holes with bags of cold-patch asphalt.
11. Wait for next bigger rain.
12. Take pictures of wet-weather creek undercutting driveway.
13. Submit online repair request to VDOT with attached photos and note of concern about possible driveway drain pipe collapse.
14. Take off work day to watch VDOT and contractor remove 50-year-old drain pipe parts, add new cement drain pipe, and add asphalt entry pad and berm to keep wet-weather creek in the ditch under the driveway.
15. Wait for biggest rain and watch the results with gratitude to VDOT!
    
         

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