First a word: some find “character” a pejorative. In this case, it is a loving title for the grand and unique folk who shaped a grand and unique village.
Charles Southmayd, 1824 — 1911, Oxbow Farm, Stockbridge, was a New York lawyer and a prominent citizen of Stockbridge. He purchased land previously owned by Henry Wadsworth Longfellow. His law partners Charles Butler (Linwood) and Joseph Hodges Choate (Naumkeag) also maintained homes in Stockbridge.
Southmayd was said to look like a character out of Charles Dickens: round in the middle with a generous mouth, bulbous nose, and fringes of hair on either side of a bald head. Also, he was said to be boring. Every year for sixty years he sent the same message to his tailor: “Two suits like the last.” He was frightened out of Stockbridge by the Gentleman Burglar, and in love with a woman who did not love him. It is said he built Butler Bridge (one of the most beautiful in Stockbridge) to shorten the daily walk to her house.
Diagnosed as bilious, he was restricted to drinking only water and milk. He ordered all his wine and liquor emptied out on the gravel path in front of the house. If he couldn’t drink it no one could?
Judging him mean, Natalie Sedgwick wrote, “Thousands of dollars’ worth soaked into the old world; enough to inebriate it and send it reeling out of its orbit.”
His junior partner, Choate was told, it was a lawyer’s duty “to accumulate and save his entire professional income.” Choate argued that was not always possible as “one must live.” Southmayd denied the logic of Choate’s argument. And yet…
Of Southmayd, Ellery Sedgwick, owner/editor of the Atlantic Monthly, wrote: “I want to pay Southmayd’s memory a personal tribute which I have carried in my heart for 60 years.
One day my father said to me, ‘Ell, if I am to save the old house, I must borrow $7,000 and I have decided to ask Mr. Southmayd for it.’ [It was 1866 and $7000 is equivalent to $136,000 today)
I see my father approach Southmayd’s door with the desperate look of the dead or doomed visible across his face. We were homeless; I had little doubt of it. Then suddenly the doorway flung open and out came my father, his ruddy face glowing with happiness.
There was no need for words, but as we trotted home, my father kept exclaiming: ‘What a kind man! What a good man!’
Sedgwick added, “The full extent of Mr. Southmayd’s generosity my father never knew.”
In his will, Southmayd left the meadows Sedgwick put up as security to the Sedgwicks.
Southmayd was undoubtably brilliant. Southmayd prepared the briefs Choate used to plead the case against income tax in 1894. The Supreme Court ruled income tax unconstitutional. It was 1913, with the Eighteenth Amendment, that the Constitution was amended and income tax allowed.
Southmayd held that the right of property was foundational and therefore, any Act of Congress instituting the income tax would require an amendment to the Constitution.
Asked how he won so handily, Choate said, “Most men are endowed with only five senses. Mr. Southmayd has a sixth— the sense of property.”

