I hunt a piece of land about 5 miles across and had to shot a Doe smack dab in the middle. So 2.5 miles crows fly, but had to weave between tow mountains, so I figure it was 3.5 - 4... I have a pretty bad back and almost lost my faculties!!
My longest by hand was only 1/4 of a mile slight uphill grade. Then purchased a polaris rzr a which and addition 100 foot of rope and never had to do it again. My shortest was in 2007 hunting a 70 acre field of corn stubble and shot a buck and dropped him right on the driving lane going to the back of the field. I actually had to drag him off the path to load him up!
The first deer I shot was a doe. After I shot her, she rolled down a hillside and almost landed in a river. It was so steep I couldnt walk up the hill unless I was grabbing onto trees. So i had to drag her up to the next tree and lay her across the base so she wouldnt roll back down the hill then walk up to the next tree and do it again. I was about 75 yards to the top, but it felt like a mile! Wayne