This is a great Abraham Lincoln campaign cover (Figure 1). The cover is postmarked "October 29" but without a year. I'm fairly confident, however, that it dates from 1860.
It is franked with a 3-cent stamp from the Series of 1857-61 (Scott 26), so it could be from as early as 1857 but that is highly unlikely. It was after Lincoln lost the Illinois Senate race to Stephen Douglas in 1858 that he began to be mentioned as a presidential candidate for 1860.
But note in particular the split-rail fence across the top and down the left-hand side of the cover. Lincoln was given the nickname "Railsplitter" at a convening of Illinois Republicans in May 1860 just before he was nominated for president. Lincoln was nicknamed the Railsplitter because he had built split-rail fences as a young man (Figure 2), and the image of a hardworking, self-reliant man appealed to voters (all male) at the time.
Figure 2 - Lincoln as a Railsplitter. Source: Dickenson College.
That fact is why I think this cover dates from the second half of 1860 and that this cover was postmarked on October 29, 1860. It is certainly from no later than 1860 because it depicts an unbearded Lincoln, and we know he grew his beard after he won the 1860 election.
The cover has Philatelic Foundation certificate number 586893, which opines that it is a genuine usage of Scott 26 on a Lincoln campaign cover mailed from Corunna, Michigan. Corunna is situated between Flint and Lansing, about 90 miles northwest of Detroit. Its destination was Blackberry Station, Illinois in Kane County about 45 miles west of Chicago.
The recipient's name is clearly written - "Ellsworth Woollcott, Esq." According to the 1860 census, there was one person with that exact name in Kane County who worked as a farmhand and was born in New York around 1830. But I don't think that was the person.
There also was an "Ellsworth Woolcut" or "Wolcott" living in Kane County in 1860. My guess is this was the recipient of the letter. He too was a farmhand but was born around in 1833 in Pennsylvania. In 1860, he was living in Kane County with his father Benjamin and his mother Betsy, short for Elizabeth. By 1863, this Ellsworth, along with his parents, was living in Vernon, Michigan, which is just six miles from Corunna. He died in 1914 and is buried in Vernon.
The illustration on this cover is listed in Abraham Lincoln Illustrated Envelopes and Letter Paper 1860-1865 by James W. Milgram, M.D. published in 1984. Milgram catalogs it as AL-82 and notes that it is probably a copy of similar designs first published by Joseph E. Baker of Chicago. Baker's versions of this cover include the imprint "Baker-Chicago" or "Published By Baker, Chicago." The illustration on this cover has been seen on white, orange and yellow envelopes. This is clearly an orange envelope variety.
It was Joseph E. Baker (1837-1914) who drew the portrait of Lincoln seen on the cover shortly after Lincoln's 1860 presidential nomination. Baker became famous for this portrait, and during the Civil War he drew many political cartoons.
In addition to "Honest Abe" and his split-rail fence, the cover features Lincoln and his two flatboat voyages to New Orleans between 1828 and 1831 (Figure 3). These voyages supposedly shaped Lincoln's attitudes on transportation, commerce, and especially slavery.
I purchased this cover at an auction in April 2023.