I’ve been exploring my postcard and ephemera collection and picking out favorites to see what I can find out about them. Judging from the geographical identification on this card – indicated by highway numbers and miles from towns, it clearly was a roadside enterprise catering to car and truck traffic on Route 20 in Indiana.
What I didn’t know is how very popular it was, not just with truckers and long distance drivers but with people living in the vicinity. Memories of it has inspired filmed interviews with former patrons who hung out there in their teens.
Bob’s initially opened in 1927, with a smaller building and was enlarged as shown above in 1932. In addition to getting business from traffic on Route 20, it also served as a stop for buses, with 10 to 15 stopping there daily. With the addition, the restaurant could host 150 patrons.
It belonged to by Robert Wiley and his wife Adah who worked there as a waitress. In 1933 it was totally destroyed by fire.
The Wileys and some relatives who lived with them were lucky to escape, although Adah was seriously injured. The Bob’s sign perched precariously on top of the central peak fell on Bob, but he was not badly hurt.
The Wileys were eager to replace the building quickly because it was on Route 20 where traffic was then headed toward Chicago’s World’s Fair. It soon reopened in a new building, shown above on a matchcover.
At some point tourist cabins were erected on land behind the restaurant. They were for travelers, but also housed restaurant waitresses.
With the new building in operation, the business continued to grow, But World War II presented new obstacles, namely difficulty in finding staff and a full range of food. At its busiest the restaurant had a staff of 40 but was down to 9 when it closed for the duration of the war. The South Bend newspaper declared it had been “one of the best-known highway restaurants and tourist camps in the middle west.”
When the restaurant closed Robert Wiley became a La Porte county deputy sheriff. Adah died in 1946. He remarried and reopened the restaurant in April 1946.
The highway set the tone for the restaurant in a number of ways. Obviously it brought travelers of all kinds, including some criminals on the run, and a jewel thieves who pulled off a daring heist in the parking lot. But stranger still — to me at least — was putting venison on the menu after a deer was killed on the highway.
Bob’s closed sometime in the 1960s.
© Jan Whitaker, 2026





It's great to hear from readers and I take time to answer queries. I can't always find what you are looking for, but I do appreciate getting thank yous no matter what the outcome.


