Thursday, August 16, 2012

Those Places Thursday–Webster Family Road Trip: Chicago, Illinois

This is part of a series of posts dedicated to the immigration story of Debs Webster and his family.

Bye Bye New York, Hello Chicago, Illinois!

Debs Webster and his family are on the road again! This time they are leaving New York and heading to Chicago, Illinois.

In my last
POST I mentioned that my uncle had emailed me with some very interesting recollections regarding this trip across the USA.  Here’s what he had to say about this leg of their journey:

“We travelled first to Chicago, where Pop’s uncle and some cousins lived. They tried to teach me some English words to no avail. Since I wasn’t using them, I had no retention of the words.”
The uncle he is referring to is Rollin Waterman Webster. He was a brother of my "Traveling Dentist Great-Grandpa" Frederick Webster. I introduced you to sweet Uncle Rollin in this previous POST.

Grandpa Debs’ 1952 photo album shows photos and a vintage postcard from Illinois immediately following those from near Palmyra, New York. With that in mind, I hope I’m correct in assuming they left Palmyra and headed directly to Chicago. If that was the case, then according to GoogleMaps, the trip would have taken about 10 hours!

My uncle also said that my Grandpa Debs was the only one in the group who knew how to drive, so guess who drove the whole way!

Palmyra, New York to Chicago, Illinois Map

According to a letter from Uncle Rollin to my Grandpa Debs, the last time they saw each other was probably sometime before 1923. So I can imagine how exciting this must have been for them to see each other again after so many years! Actually about 29 years! In 1952 Uncle Rollin would have been about 80 or 81 years old.

The photo below of Rollin was taken in June, 1952 in Chicago. The young man behind him is his grandson Billy.

In 1952 Rollin was living at 8937 South Paulina Street in Chicago. According to, his house was built in 1924. Today’s stats say it is 1,087 square feet in size, and has 1 bathroom. It doesn’t list how many bedrooms it has though.

Rollin Waterman Webster June 1952
Rollin Waterman Webster and
Grandson Billy in Chicago - 1952

Rollin Waterman Webster June 1952 pg. 2 back of photo
Back of Photo

The following photo of Rollin was taken in 1942 at the Chicago Loop.

Rollin Waterman Webster 1942 at Chicago Loop
Rollin Waterman Webster
at the Chicago Loop - 1942

Back of Photo
Here’s a map of the Chicago Loop from Wikimedia Commons. It was created using Ever heard of it? I hadn’t until I wrote this post. It seems pretty cool. And yes, I’ve added the website to my blog’s Research Toolbox. Here’s the LINK to the Chicago Loop map on

Chicago Loop
Map of Chicago Loop from
Wikimedia Commons via

I don’t know how long my Grandpa Debs and his family stayed in Chicago visiting Uncle Rollin and his family, but I’m sure they had a wonderful time.

Unfortunately, it is time to get going again for Debs and his family. The next photos and vintage postcard in Debs’ photo album are from Galena, Illinois.

Why did they stop in Galena, Illinois? Tune in next time to find out.

Thanks for reading!

Copyright © Jana Last 2012


  1. I wonder if they broke that 10-hr drive into 2 days. I sure would have! That Debs was the only driver is no surprise. I remember my grandmother and even my mother getting their driver's license when I was almost in high school.

    1. Hi Wendy! I imagine they would have broken it down into 2 days, especially with three kids and a 66-year old grandmother in tow. Six people crowded into a car with no air conditioning during the summer. Yikes!

      My Grandma Willis did get a driver's license once she came here to the States.

      Thanks for reading and for your comments!

  2. I'm thinking that ten hour trip would be taken in two segments, too. The roads back then weren't as streamlined as they are today (er, well, as they are supposed to be today ;)

    Do you know if that Chicago home is still standing today? I was just back in Chicago visiting relatives and someone mentioned that the family house in the city was just torn down. Though I've never seen it myself, at least there are online sites that make it possible to "see" the neighborhood as it was a few years ago. Sometimes, that is all that is left of our ancestors' homes--just the pictures.

    1. Hi Jacqi,

      I wonder just what the highway system was like back then. That would be interesting info.

      As far as his Chicago home goes, I tried to find it on GoogleMaps streetview, but it wouldn't go to the correct address. Frustrating! It's weird too since listed home's address so it must be there still.

      Thanks so much for stopping by!

  3. I am thoroughly enjoying reading about this part of our family's history. Thank you, Jana!




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