The job may be easier/harder than you think (Easier cause you need spend less money, harder due to cable routing).
First: If you are talking over the air,, There is no such thing as an HD Antenna, it is an antenna period,, DirecTV has HD antennas, Dishnetwork,, the 1000 antennas are HD, but OTA you just say ANTENNA.
Now to the issue:
if your "Booster" (which by the way it is not) is a wall plate, then on the back there should be a 3rd port which is named TV-2 (will likely not be labeled) the 3 ports, left to right, with the 12 volt accessory socket at the top, and looking at the back are
Rooftop antenna = Park Cable = TV-2 (And if there is a 4th TV-3)
As the other person said, so long as both stations are on the same heading (no need to rotate the antenna) will work very well.. I know.. I do it that way
Recommendations:
1: Use quality RG-6, not RG-59,, often the cost is the same in 100 foot or less rolls but the signal delivered may be much better with RG-6.
2: you night consider changing that wall plate to a SENSAR PRO if your antenna is a winegard Many many advantages
Home was where I park it. but alas the.
2005 Damon Intruder 377 Alas declared a total loss
after a semi "nicked" it. Still have the radios
Kenwood TS-2000, ICOM ID-5100, ID-51A+2, ID-880 REF030C most times