The following single command line in a Windows Desktop shortcut Target field will ping an address and timestamp it.
C:\Windows\System32\bash.exe -c "ping 1.0.0.1 | while read line; do echo `date` - $line; done"
Example output:
Fri Nov 27 14:08:05 CST 2020 - PING 1.0.0.1 (1.0.0.1) 56(84) bytes of data.
Fri Nov 27 14:08:05 CST 2020 - 64 bytes from 1.0.0.1: icmp_seq=1 ttl=58 time=26.7 ms
Fri Nov 27 14:08:06 CST 2020 - 64 bytes from 1.0.0.1: icmp_seq=2 ttl=58 time=35.5 ms
Fri Nov 27 14:08:07 CST 2020 - 64 bytes from 1.0.0.1: icmp_seq=3 ttl=58 time=42.0 ms
I read here that wsl.exe should be used instead of bash but I cannot figure out how to create the equivalent command.
(To do any of this in Windows 10 requires that you enable "Windows Subsystem for Linux" in Windows 10 and install Ubuntu from the Microsoft Store per this HTG article.)