You may want to consider Mt. Waternomee. Have some fun researching WW2 history with your buddy before you go and then do the hike. He can share his history lesson next fall at his school with photos and facts by doing a show and tell. There are many sites you can google to become familiar with the story. Here is one.
http://www.hikenewengland.com/Watern...rash070916.php