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Throwback Thursday: Oldest Known Downtown Photo – 1871
By Eric D. Tudor
Ever wonder what the oldest known photo of Downtown Lebanon looks like?
You might recognize it – the 1871 image of Commercial Street, looking west from the Jefferson intersection. But even if you’ve seen it before, do you know the story behind it?
Let’s set the stage. It was just after the Civil War. Lebanon was still divided. Unionists and Confederates both called it home. Bushwhackers roamed the woods and wagon trails. Just a few years earlier, the nearest railroad was over 100 miles away. Our little “oasis” had a Wild West feel, full of travelers, gun-toting citizens, and tough pioneer life.
Point of Interest 1: The photo’s journey
This photo originally belonged to the Diffenderfer and Greenleaf families, both early pioneer names in Lebanon. It was donated to the Lebanon Public Library (Kinderhook Branch on Harwood) by Mrs. W.I. Diffenderfer and Miss Georgia Greenleaf. That building today houses the Allen & Rector Law Firm, next door to what was once the Old Diffenderfer Home, built in 1870. Today, that location is Lebanon Manor (the high-rise apartments). For decades, up until the 1960s, this historic photo hung in a downtown bank. While the exact one is debated, it was likely the Bank of Lebanon, where W.I. Diffenderfer once worked as a bank clerk.
Point of Interest 2: A street frozen in time
The image captures a dirt road lined with wooden buildings, ox teams, and wagons. A sign in the background reads “Rubey and Ivey”. C.W. Rubey, an early pioneer, was the father of future Congressman Thomas L. Rubey. Mr. Ivey was related to Mrs. Elinore Watt and Mrs. Eugene Hooker. In the center of the street sits the town’s public well, used by farmers and townsfolk alike.
Point of Interest 3: Faces from the past
Yes, we even know some of the people in the photo. The woman in the wagon is Sarah Lillard. The man leaning on it is her husband, Daniel Lillard. They were part of another founding family in Laclede County. A third man, standing to the left, is believed to be a milk deliveryman.
Point of Interest 4: The well remembered
That old town well, the only confirmed landmark in the photo, stood at the heart of “New Lebanon.” It remained intact for over a century until the early 1980s, when it collapsed in front of what is now First State Community Bank. What started as a small sinkhole quickly widened, shutting down an entire lane as the city worked to repair the damage.

