Hi. I was woundering if anyone could help with a backpacking question?

The most, or should I say the longest, I have backpacked was just over a week and it was on trail. But I was wondering what it would be like to just go off the trail and go from one town to another that is about 250 miles apart or allot longer, and with out any help drops; no outside help, just us girls on our own. What different gear should we be thinking of getting? Is there a list of stuff to bring? I have been using an old army pack from the 1960s but nothing else army. It seems a little butch to dress up in army gear but if the men in Vietnam used to hike allot using it, why not me? Any suggestions or help? And if there is any female soldiers or backpackers out there who could help with suggestions about personal hygiene when left out in the field, it would be very helpful. Thank you all.