Charlie Sherman was in great demand and welcome at just about any event he favored, for attracting a crowd was the key to success, and few folks could attract a crowd like Charlie could. He followed an itinerary that lasted for decades, traveling from fair to fair, selling his wares (sometimes vegetables, berries, peanuts, or soda) and working as a huckster, promoting other vendors and exhibits. Roaming the grounds, he delivered spiels, sang, pontificated on everything from politics to local history, talked about his past, and spouted witty sayings, often in poetic fashion. It was a win-win situation, adding to an event’s atmosphere while putting the spotlight on Charlie — and the more attention he received, the more he liked it.

He was already known far and wide as a beloved eccentric, but — either to maintain his status, or because innate quirkiness guided his impulses — Charlie upped his game in the early 1900s by expanding his wardrobe in unusual ways. Whatever the reason, it played out over time as a roaring success.

In September 1900, Watertown hosted what the city’s Daily Times called “the biggest Labor Day celebration in local history…. One of the day’s attractions is Huckleberry Charley. He is in from the veldt with a carefully trimmed goatee slightly tinged with gray, a silk hat and frock coat [knee length and split in the back] and a pair of trousers that can almost talk in several languages [outlandishly multicolored].” Another outfit he wore in the past included a bright scarlet vest, checkered pants, and a top hat.

The Times also noted his return in September 1901: “Everyone is glad this year to see Huckleberry Charlie, who is as meager of person and as sound of lung as ever. Charlie is dispensing peanuts, and doing it with that lavish sangfroid which distinguishes all his actions, whether large or small. His stamping ground is the grandstand at the race track, and between sales he strikes attitudes and tells the crowd about things in his inimitable way. He discourses of sauerkraut, huckleberries, and mail routes, and takes the bunch into his confidence in the way that no one but Charlie himself has mastered…. Charles is a wisp of a man…. On Tuesday he wore a red vest, but it scared the horses, so he obligingly took it off yesterday and appeared as a shirtwaist man in suspenders.

Charlie was enjoying life, but from 1903 through 1907, family troubles periodically caused turmoil. At issue was the mental health of his younger brother, Robert, who had recently arrived from Chicago. A jeweler by trade, he began bartering his stock for a pair of horses and about a dozen wagons, buggies, and cutters. The mounting stress of arranging many deals was blamed for his gradual separation from reality, which became evident through odd or irrational behaviors, extreme nervousness, and an obsessive belief that others were trying to steal from him.

Two doctors examined him, and after agreeing with their assessment that Robert needed treatment, Charles signed the papers committing his brother to the St. Lawrence State Hospital in Ogdensburg. The official causes of his insanity, they said, were horse trading and heredity. The latter would one day have an effect on Charlie’s own life.

In 1904, their mother died, and for the next three years court action was initiated by several family members who contested her will. Despite those issues, Charlie continued the tradition of attending fairs, holding court of his own before hordes of admirers while wearing colorful, unusual clothing and reveling in all the attention.

But in 1908, a year after the family problems were resolved, further change came to Charlie’s life in a big way. Pine Plains, a source of both his income and famous nickname, Huckleberry, was invaded by the military. Men had trained there in limited numbers during previous years, but by law, the National Guard was made part of the country’s defenses. Military leaders ordered a training regimen consisting of joint maneuvers with the regular army. For that reason, many states battled at the congressional level to host training sites. Among the winners of the fierce competition was Jefferson County’s Pine Plains.

Lengthy preparations were made to host large contingents of men from several states, and for the first session of training and maneuvers, ten thousand troops began arriving on June 14. (All would depart by July 15.) They included National Guard units from Connecticut, Maryland, Massachusetts, New Hampshire, New Jersey, New York, Pennsylvania, and Vermont, plus ten units of regular troops ranging from infantry, cavalry, and field artillery to engineers and hospital corps.

For the host county, they represented a financial coup, but for Charlie it was something else entirely. The troops gathered well ahead of berry season, but their activities damaged countless plants. The only plus was that it earned him unexpected attention when legions of berry pickers arrived later in the summer and sought his advice, for only Charlie knew where the best sites were that remained intact.

Despite the unwelcome military intrusion, he made the best of it by exploiting new sources of income. To keep the men in touch with national and world events while deployed in such a remote area, he regularly toured the camp and sold newspapers from tent to tent. Among his customers was Major General Frederick Grant, the oldest son of the former president. Other wants and needs were provided to the men as well, including alcohol, which was forbidden within the camp — meaning it fetched a good price. Unruly behavior caused by frequent drunkenness was cited by officers in post-maneuver reports as one of the problems to be addressed before future sessions were held.

Charlie also helped cause a stir involving the 24th US Infantry from Maryland after the men, while setting up their tents, disturbed the ground and found what appeared to be remnants from old tombstones. He confirmed it was a cemetery from early pioneer days, causing a ruckus among them for fear of bringing bad luck to the outfit or visitations from unfriendly spirits.

After the military left in mid-August, Charlie tended to picking and selling huckleberries before making the annual circuit of fairs, taking with him a supply of gaudy clothes, goods to sell, and stories to tell.

In early December, he branched out by appearing in an amateur talent show held at Watertown’s City Opera House in conjunction with a performance by the Grahame Stock Company. He was the only comedian on a roster that included acrobats, singers, dancers, magicians, and other talents.

In 1909, Watertown’s Fourth of July celebration drew thousands of regional folks, the perfect situation for a man like Charlie, of which there were few. As usual, his antics and clothing ensembles enhanced the experience for many attendees. Said the Daily Times, “Huckleberry Charley was favoring the city with his presence, and Charley certainly enjoyed himself.”

In September at the Jefferson County Fair, he hosted a small reception for the 24th Regiment Band, added to the general merriment with his carryings-on, and operated a soft-drink stand. At night he took the stage at a local theater, said the Times, where, “He does a song-and-dance sketch much to the delight of the audiences, and receives encore after encore.

“  ‘Came down to Watertown, sold all my huckleberries, went home with plenty of granulated sugar and made my cologne bottle smell 50 percent sweeter,’ says Charlie on the stage. Then he follows up with, ‘These huckleberries were picked on the Pine Plains, are free from sticks, stones, stems, and bruises. Some are black and some are blue. Come up kind people and purchase a few. This is my last time through. Get your huckleberries.’ ”

He was also known for telling anecdotes that ended in one version or another of his favorite and most confusing saying: “I didn’t get as many berries as I expected to, but then again I didn’t expect to,” or, “Things are not as bad as they expected they would be, and they didn’t expect they would be neither.” It was vintage Charlie. And in his late sixties, he hardly seemed to be slowing down.

Next week, part 3: taking the comedy stage; messing with the army; wild partying.

Photos: Charles Sherman; St. Lawrence State Hospital at Ogdensburg (postcard, ca. 1900); on left, General Frederick Grant and Governor Charles Evans Hughes at Pine Camp (LOC, ca. 1908); headline (Watertown Daily Times, 1908)