Thanks for the ideas and suggestions. The current plan is to do the Slide, Cornell Wittenberg trail from the parking lot by the rod and gun club. First day with a pack will be somewhere around 4 miles. It might be a little more as there are two routes to the top of Slide. One is steeper so I will see what looks like the best way for him the day of. The next day would be a day hike out over Cornell and Wittenberg which is also about 4 miles. Then the next day we would be back to the car. Overall I think it is a doable route and even if we have to take a lot of breaks 4 miles shouldn't take that long. 

Once before he enjoyed a scavenger hunt on a day hike, so I made up a few for him to do with plants and animals I would expect to see in this area. He seems excited about that. I also decided to add a little weight for him to carry in the way of a digital camera. I thought he might find it fun to take pictures of what he finds interesting rather than just what I thought looked cool.  

My son also loves Legos and made a "camping" figure for both of us and the pup. Not sure why but for some reason I am carrying a machete...but maybe that was the only knife he had. But I suggested he bring them and we can set them up in places to take their picture, then we can recreate the same picture. It might be an epic fail, but he was interested in having something to play with a a little and being plastic I figured we wouldn't have to worry about them getting ruined in the rain.

The ice cream on the way home sounds like a great idea, I will have to watch for places on the way up. If nothing else my son loves to eat and ice cream is always at the top of the list. So talking about a nice cold treat when it might be warm and humid out might be a good diversion.