My 4th grade class did something like this as well, and I thought it was awesome. We had to write out a family character sheet of sorts, and choose what equipment to buy and bring. The students were grouped into traveling parties of 4-6 families.
In retrospect, I think the random encounters were done well. Instead of dice rolls, your success/failures were usually like this:
- automatic success if you choose the right path or brought the right stuff
- skill based success with scaling difficulty if you choose other paths, usually 'throw a penny into the trash can from 5 (or 10 or 30) feet away'. If you failed they didn't kill your party, but they made you write a report on whatever you failed at.
An example would be 'You're travelling through the desert, and there's lots of snakes and scorpions. You have to be careful to check your boots each morning before you put them on, or you might be bit.
Remember to check your boots by throwing a penny into the trashcan from 10 feet away. If you fail, write a 3 page research paper on snake bites.'