With the 8 speed shuttle (stick) transmission you have there is no such thing as the turtle or rabbit as seen on hydrostatic lawn machines for slow and fast. You select the gear that fits what you are doing and use it. Your trans is probably a 4 speed stick with a high and low range. The high and low range might even be labeled with a turtle and rabbit which is irrelevant. Lowest gear (greatest mechanical advantage) is first gear, low range. Highest (fastest but least mechanical advantage) is 4th gear in high range.
Very likely shifting gears within the 1/2/3/4 positions is synchronized (meaning it won't scrape and make a nasty noise when shifting among those gears while moving.) Shifting between low and high range is probably NOT synchronized and that means you need to stop to shift ranges. Dear me, read the operator's manual.
No one can tell you which one. Just do it. It will become natural for you to pick a medium rpm engine speed around the standard rated rpm for the engine and tractor (read your operator manual!), then select a gear, let out on the clutch and proceed. If it feels to you like it is struggling or lugging down, shift to a lower gear. If it feels like it is too easy for the tractor, shift to a higher gear or back off on the throttle. You may or may not need to shift a few times as you maneuver over your pasture while cutting. You just gotta get out there and get some experience. No one can proscribe this for you.
I am going to ask an important (and certainly not meant to be offensive, ) question: Have you driven standard transmission cars/trucks or tractors before? That makes a big difference in fully seeing your situation.