In general, an ASOS or an AWOS can be heard 15-50 miles from the associated airfield, depending on altitude, weather, transmitter power, etc. It is designed to be received by aircaft on the ground at the airport, and by airborne planes inbound to land. Monitoring from the ground is difficult more than 1/2 a mile from the field. For those on the ground, the ASOS/AWOS have telephone numbers that you can call to hear the recording that is transmitted.
CA
Annapolis