The annual Coaching Day parade held in Monticello in September 1899, at which a variety of fanciful and colorful decorated floats rolled from the former county fairground down eastward on Broadway, was attended by roughly 6,000 people, according to a contemporary observer.
The Republican Watchman reported on its front page of September 8, 1899 of the above pictured float that took part in the parade: "John Osborn won second prize. His display was a wagon filled with dilapidate household effects, chicken coops, etc. The occupants were a colored couple and two pickaninnies. On top of the wagon was a sign bearing the words 'Moving to Dogtown.' Although the latter was more burlesque, in the opinion of the judges a steer hitched to a wagon was more of a novelty than a mule hitched the same way" [source]
The float's maker, dentist John Osborn, died at the early age of 28 in 1908, nine years after the event. According to an Osborn family genealogist and relative, Susan Benton Schock, John would have been 19 or 20 when he made the float shown in the photo at right. It is unknown whether the above photo pictures Osborn himself, with adult riders wearing black-face.
The origin of Monticello's the "Dogtown" name is unknown. Nor is it known why this section of town was chosen as a theme for the Osborn float. Despite using an overtly racist word that a modern source politely calls a "derogatory term for black children", the Osborn float earned second prize in the parade. Nowadays the driver would be lucky if he wasn't pelted with rocks, or worse.
A June 9, 1899 edition of The Republican Watchman reported that Dogtown resident Mrs. Charles Webber had her neighbor, Henry J. Weasmer, arrested for allegedly poisoning her hens and pigs with a "biscuit buttered with Paris green". Town justice William B. McMillen issued a warrant and the defendant was brought before him, according to the news account. In the ensuing trial, the Watchman reported, "...considerable evidence was taken, much of it extremely contradictory in its character, and the court, after giving both parties an admonition to abstain from the unneighborly bickering with which they had disgraced Dogtown for some months, discharged the defendant." [source]
Henry and Lila Weasmer and all of their immediate neighbors - including Charles and Mary Webber (the defendant in the above poison biscuit case) - are listed in the 1900 census are listed as white. [source]. Interestingly, John Osborn, age 19, lived in the same neighborhood [source]. So whether African-American families lived in what Monticello residents knew as "Dogtown" remains uncertain, despite local legend.
Writing in March 2011, local restaurant chef Andy Yeomans offered the theory that Dogtown area of Monticello "...was the area of town that was built up as an ethnic community. Much like NYC having Irish, Italian, Chinese, Afro-American groups of homes,... it has been suggested [this] was the case with Dog Town. Afro-Americans grouped in that neighborhood owned dogs that would run loose in the area. Kids back then dubbed it 'Dog Town' and they knew they should avoid it out of fear of attack by dogs. I have no idea if there is any validity to this, but it's something that was shared today by a customer I asked."
Longtime residents remember Dogtown as it was before the middle of the 20th century as an area where low-income families lived. Former village building department employee Jim Carnell informed this writer that a brothel existed in the area in the Dogtown area during the 1960s. Prior to that, according to Monticello resident June Barthol, a dog pound once stood in the area.
Sullivan County historian John Conway provided a scanned image of a 1936 ticket to for the Monticello Greyhound Association, which reportedly held events in the Dogtown area, near the old county fair-ground. In an accompanying e-mail he noted, "...Of course, everyone used to call that area Dogtown. I know there were dog races held there at one time... but Judge [Lawrence H.] Cooke once told me that the name pre-dated the races. The dog pound story [see above] makes sense, but I cannot vouch for it."
Equally possible, "Dogtown" may have an old generic descriptive term for areas where squatters lived, with run down shacks that was applied to a specific location in Monticello because it fit the colloquial meaning.
(Photos courtesy of William Horton and John Conway)
Monticello has always been a diverse community. African Americans lived here since the settlement was founded in 1804 when history records that Samual F. Jones, one of two brothers who founded the village, owned at least one slave who was of African descent. Judge William Thompson also owned at least one slave, a woman by the name of Jenny, who lived in Monticello past 1850. For a partial list of heads of household listed as "Black" or "Mulatto" in federal censuses between 1860 and 1920, see this link. Black faces are rarely seen in Monticello class pictures until the about the 1960s, but there is no denying this part of Monticello's long heritage.
[1] Sullivan County Historian John Conway added, "...a son of the couple you mention, was a well-known peddler in Monticello for many years in the mid-20th Century. He dressed like a homeless person, but the scuttlebutt always was that he was extremely wealthyand a miser. He lived in a large house with a housekeeper in Dogtown, and they operated a small store there for some years. i would say he died in the mid-1960s."
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