You have no way of knowing since this is a new location for you
opps..i mean the minimum, but since you are asking for maximum..many miles should be the answer.
Okey i will get it..
What's the maximum distance you might walk on your path . The shortest path that guarantee reaching the road has minimum and maximum. Maximum ..without walking back.
As I understand the question : What is the shortest or minimum possible distance to ensure reaching the road? Since the road is possible to be circular that maximum is also minimum.
To make it maximum we take the road to be a none straight end of the road.
So even it is a straight one if it is the " end of the road" (non tangential) the answer is still 1+2pi..