The First Post Office in Whitmore was officially established January 5, 1885, with Simon H. Whitmore as the first postmaster. Before 1885, the United States Postal Service called the Whitmore postal area, "Tamarack (no post office)."

Simon (or Samuel) Houstin Whitmore had a blacksmith shop and way station on Tamarack Road, seventeen miles northeast of Millville. Every week when he went to town for supplies, as a favor to the residents of Whitmore, he picked up their mail in Millville, and delivered it on his way home. In the early 1880s, the residents petitioned for a post office, and asked that it be named after Simon Whitmore. That is how Whitmore got its name.

The mailboxes, before automobiles were used for delivery, were locked leather bags hung on a crosspiece on a pole. The bag had to be at the right height for the mail carrier to reach from a wagon or horse. The carrier would take the leather bag down and hang up the new one. Mazie Phelps Saunders said:

When David E. Covey was the mail carrier, mail was delivered daily to the post office. Covey was the carrier for about twenty-five years. In winter he rode horseback, some times with pack horses. In summer he used a horse and wagon. We called it Mr. Covey's stage -- but it was just a wagon. There were two seats, and two horses pulled it.

The mail carriers were contract employees, not employees of the post office. The carriers could carry on a side business, such as picking up supplies in town and delivering them along with the mail.

Jim Bogue grew up in Whitmore. He tells about the old-fashioned star route:

My father worked out of town, and my mother didn't drive. Mother would give the star route driver the grocery list. It seems like he charged fifty cents for doing it. He'd always look for the specials, and he'd look here, and he'd look there, and he'd never make money on that. That's where we got most of our groceries.

Elwood Ward tells a story:

I don't know what year it was, about 1930 or 31. Old Ed Hufford was still the postmaster in the store. I was working for this fellow that had the mail route at that time. Carried the mail out of Redding, up around Whitmore, Fern and back through Millville again. We had a big snow. They had two feet of snow in Millville. The county had a Caterpillar tractor, called a 30 Cat. Across the front it said "30."

[To clear the snow] we started pulling the grader. It had the motor built in. I was driving the Cat, and the other fellow was driving the grader. We only made it up as far as what we called the old Rose Hill [old Whitmore Road], about two-and-a half miles above Millville, and it [the Cat] slid off of the hill.

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