All wire has resistance; that is why we have to consider voltage drop. For the circuit in question the expected resistance is nearly 4 ohms because it is so long.
With 120V at the supply, if you short circuit the end of the circuit, 30A will flow through this resistance.
Now you have to look at the 'trip curve' of a circuit breaker. When the handle says '20A' this doesn't mean that the breaker will carry 19.999A and instantly trip at 20.001A.
A perfect circuit breaker follows an inverse time curve, meaning that it takes a certain amount of time to trip at a given overload, and trips more rapidly the greater the overload. On top of this real world breakers have a tolerance range where operation anywhere in a range of times is acceptable.
Well it turns out that for a normal 20A breaker, it is perfectly reasonable for it to carry 30A for minutes or longer...or to trip in 20 seconds.
See for example
https://download.schneider-electric...+curves&p_File_Name=730-3.pdf&p_Doc_Ref=730-3 where for this particular 20A breaker a 30A load will trip the breaker between 22 seconds and 125 seconds.
-Jon