Keep in mind that Henry was not cutting thru the old train tracks. He went up to the small wooded area above the town DPW.
The way he was heading home was pretty much the most direct and common walking route from Vinnin Sq. /CVS to his house. It is the way I would have walked back then to get to his area of town from Vinnin Sq.
His sister stated that where he cut up was not a short cut, which I would agree with.
.....As someone not personally familiar with Swampscott, I wonder whether Henry and his fellow high school students regularly used the old Swampscott Branch right of way to walk downtown?...
Maybe he had heard from the high school grapevine that it was safe to use the abandoned right-of-way and then cut to Suffolk and Franklin, an easy route to describe?
The old tracks that ran from Walker Rd. up to the old Jr High/HS/MS, was used very regularly as it was a direct route to the school and had easy access in multiple places. You would find kids walking along that route, playing in the woods near there, riding dirt bikes, etc. on a fairly regular basis.
The section in question that ran across Paradise Rd. was not used very often as it was a bit difficult to get up to, even for a kid, and it did not save time. On Paradise Rd. there was a high stone wall and I believe a fence that made it a little difficult to get up to the old train tracks from Paradise Rd.
Like many kids, I often walked along the old train tracks that ran to the Jr. High/HS/MS, but I think I only was on the other portion a couple of times and I grew up near there.
Maybe some mean homicidal troll-like person or persons was hiding in ambush near or on the old bridge abutment for high schoolers or whatever that cross Paradise Road from the area of the high school?
I used to think it was something like that but I think that is doubtful. It was not a common area so if someone was waiting to ambush a kid walking home thru there they could have a long wait. I had thought previously that maybe a homicidal troll like person saw Henry walk up there and is was a crime of opportunity but Henry veered off to that area for a reason so I think it is more likely he was meeting someone.