@Gabby,
At 300' it would be a whole lot better to put a sub panel in your shop with breakers than to try to bring one line with outlets.
Wire size ( 0 ) Maximum amps for power transmission( 150 )You could have 7-20 amp circuits.
Wire size ( 1 ) Maximum amps for power transmission( 119 )You could have 6-20 amp circuits.
Wire size ( 2 ) Maximum amps for power transmission( 94 )You could have 5-20 amp circuits.
Each circuit would be 120 volts.
One circut could be used for lighting.
Most extension cords for regular duty use are 14 awg or 12 awg at best.
12 awg at 300 ' pulling 20 amps will have a voltage drop of 19.59 v leaving you with only 100.41 volts to work with, really being unaxceptable.
This is just a suggestion/estimations but I feel this would work better for you.
