I suppose it depends on whether or not he is being chased by brown bear one!
Actually, it is a mathematical impossibility: no bear nor any other living thing can travel 1000 square miles.
A square mile is a measure of area in 2-dimensional space whereas what you might be after is a measure of distance in 1-dimensional space. The two measure different things and, according to basic principles of dimensional analysis, any attempt at conversion from one to the other is fundamentally flawed.
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on average they can travel 1000 miles....in one day
1000 acres = 1.5625 sq miles.
You are travelling at 100 mph. That means (obviously) that every hour you travel 100 miles, and since 1000/100=10 you will be travelling for ten hours.
It is about 1.56 square miles in area.
1000/30 = 33 hours, 20 mins