Two Brothers on Harleys from Chicago to Daytona Beach -- in 1950

I was cleaning out some of my late father's papers and found a small collection of photos of him and his younger brother Jack on their Harleys. The back of this picture has a date stamp of July 21, 1949. He would have been 21 years old at that time. It looks like it was taken in the yard of his house in Chicago.

Can any of you Harley aficianados tell me what kind of bike this is? I know he also owned an Indian at one time, but I think this is a Harley.



Couple of other, B&W pictures taken at the same place, probably around the same time:





My Dad's older brother Verne was a tail gunner in a bomber over Italy in WWII, and my dad told me that Verne gave him this sheepskin jacket for riding in cold weather:



My late uncle Jack on his bike:



Another shot of my late uncle Jack:



His family had a summer place up on Lauderdale Lakes, Wisconsin and I know he made the trip back and forth between there and Chicago on the Harley many times. Here he is at the lake house, in a very faded picture. The goggles pushed up on his forehead suggest to me that he has just come back from a ride.



Back then you could apparently blaze away with a firearm in your yard; it probably would be frowned upon in this day and age. I can tell from where the boathouse is in the background that he is firing out over the lake:





My dad used to tell me about how he and Jack rode their Harleys from Chicago to Florida and back. They made this round trip several times. I regret not asking him more about these trips. He told me one anecdote about stopping in a small town in the deep south to eat in a diner; a rain storm came and passed and when they went out to their bikes, they found that a black man had come out of the barbershop they had parked in front of, and spread newspapers on their saddles to keep them dry. He was touched by this gesture and recalled it years later. He wondered whether it was a kindness that would be shown to any traveler, or if it was because of their Illinois license plates -- land of Lincoln.

Looks like they made their way on these big bikes on some off-road trails as well. The plate here reads '1950.'



Florida state line. You can tell from his deeply tanned arms that he did a lot of riding in a t-shirt:



Looks like Florida to me:



He told me he rode his bike on Daytona Beach, although I don't know if this was taken there or at one of the other Florida beaches. This pic is of Jack, so I figure my Dad took the picture.



On this print there is the edge of another photo including part of a sign that reads 'EER,' which I think must be 'BEER.' But if there was another photo of them and their bikes in front of some road house, it is gone forever.

On the road:



In this shot and another one above, he is wearing a handkerchief to keep his hair clean -- never a helmet. That's what he told me by way of recounting his crash coming back to Chicago one night from Wisconsin. He hit a pothole and went over the handlebars and dislocated both shoulders; he taught me as a teenager how to put my foot in his armpit and pull on his arm to relocate it. In that crash he also hit his head and suffered a subdural hematoma that put him in a coma for weeks. He recovered with his faculties intact -- or at least enough of them to go on to go through medical school and become an anesthesiologist.

He was an adventurous man -- he later did mountaineering, climbing Mt. McKinley and Aconcagua, and Kilimanjaro twice -- once with me. Later in his career he spent years in Africa both teaching and practicing medicine including in remote areas of the Congo and what was then the Central African Empire.

photos and stories. Thanks for sharing.
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Wow, it's not every day one gets to read a ride report from 60 years ago. Thank you.

I love it when people post old stuff!

Do you have any of the bikes or the old jacket? I love these old pictures. Thank you for sharing!

Fabulous pics. Thanks very much for posting them. Sounds like your Dad led a great life.

great pics and story, love those old bikes

Man, that is just too cool! Gotta love the way they "rode what they had" back then.

great Photo's! Your father's bike appears to be a 1946 WLD model and your uncles a 1947 WL, both 45 ci models. Good Stuff.
Check here http://harley-davidson.oldcarandtruckpictures.com/ for some comparisons.

Awesome pictures and stories!

Awesome story and pictures! Reminds me of some of the photos my mom has of my grandfather when he raced Indians. There's just something, I don't know, happier/free-er/etc about those days (plus the bikes were bitchin').

Love this stuff.

Wish I could have met your dad.

That was lovely. Thanks for sharing them with us. Hope your Dad and Uncle are on the great road trip in the sky.

Thank you, that's very interesting.

Thanks to all of you for your very kind comments.

I have no idea what became of the bikes but I did have the sheepskin jacket, which had become as delicate as tissue paper, so that you could literally poke your finger through it, and eventually it literally fell to pieces.

But I still have his other riding jacket, of brown horsehide with a gold winged Harley Davidson patch on back, that I gave to my own son to wear.

Found this thread...Loved it!

thank you..this just moved way up the ladder on bestus ride reports ever..

Thanks much for finding this and reading it, guys. My regret is that I didn't learn more about this when I could, and now never will.

thank you for posting this. "Greatest generation" !!!!