In the summer of 1940, Dad worked for Dutchland Farms in Hartford, Connecticut, (per his first post-college resume). In the mid 2000’s, Judith and I drove with them from Bethpage to Whitman and back. As we were departing Whitman, he told the story of working as a waiter and soda fountain attendant during the week and hitchhiking back to Whitman for the weekends. On one trip, he only got partway home and had to sleep rough in a town square. We weren’t in a big hurry, and might have been planning to stop and visit Judith’s sister, so we detoured to visit the scene of the crime.
Alas, my memory fails, and I can’t remember whether we took Route 44 or Route 6 to find the town square, but I do remember driving around it. Both routes go through Providence, RI, but 44 continues to meet Mass Route 18, which goes north to Whitman and connects to Mass Route 27 into Whitman Center. Route 6 continues on to Cape Cod and intersects with Mass Route 58 which goes north through Halifax to become Plymoth Street in Whitman. I recall that our detour was mostly through small towns, so my guess is that he camped along Route 44, since Route 6 is more built up these days..
The old Dutchland Farms is gone, but the windmill above the front entrance still remains.

