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A September 8, 1900 Australian paper, reported that Dennison and a 60-piece band sailed out of Boston for a “tour of the principal European cities.” The newspaper hadn’t gotten the word that the trip, and the tour of the eastern U. S. to raise funds for it, had been called off in May by school authorities. They gave the reason for the cancellation as the estimated cost of $15,000 “…was not feasible from a financial perspective.”

The June 15 edition of The Indian Helper reported, “The band has given up its trip to Paris and has disbanded. Many of the boys have gone to their homes in the west and some to the schools whence they came. Storekeeper Kensler has taken charge of the instruments and there will be no band music for some time.” Included in those dispersing were Dennison’s younger brother clarinetist James Riley Wheelock (often referred to as James or J. Riley) and noted violinist Zitkala-Sa (Yankton Dakota). In late-June, friends and coworkers gave Louisa and Dennison silver spoons, forks, and knives as going-away presents. Mrs. Cook recited a poem she had written in their honor. They left to visit with her family and rest in Minnesota.

 In October, Dennison, who was then living in DePere, Wisconsin, took a position as a reporter with a Green Bay, Wisconsin newspaper. Later, he told a Lawrence Daily World reporter “..he would rather be a newspaper reporter than anything else he had ever known.” No article under his byline has been located to date but he may have had pieces published without attribution. He must have had some abilities as a writer because he won second prize in a writing contest at Carlisle in 1887. Although not eligible to vote yet, he  campaigned for Republicans throughout Brown County.

The next month, he obtained the “contract for getting out a large quantity of popular from the Oneida Reservation for the Pulpwood company of this city [Appleton Papers?].” How he intended to accomplish this work wasn’t mentioned.

In February 1901, he gave a talk to the Epworth League’s annual state convention in Marinette, Wisconsin. The League was a Methodist organization of young adults from 18 to 35. Newspapers sometimes confused Dennison with his football-playing cousin Martin Wheelock.

 In March, De Pere News announced:

“Dennison Wheelock has been given the contract to organize an Indian band for the Pan-American exposition at Buffalo. He will recruit a band of sixty pieces and will have his headquarters in New York.”

In July, he served as Assistant Conductor and cornet soloist for the Carlisle Indian School Band at the Pan-American Exposition in Buffalo, New York. Carlisle Bandmaster Lt. Joel B. Ettinger conducted the forty-five musicians. Moses Shongo (Seneca from New York) was the solo cornetist. Prior to going to Buffalo the band played two concerts at Reservoir Park in Harrisburg, Pennsylvania, a short train ride from the Indian school. The afternoon concert opened with a march titled “Carlisle Indian Band” by Wheelock. This might have been his “Carlisle Indian School March.” The band played entirely different pieces for the evening program.

In March 1902, Dennison took the job as bandmaster for Flandreau Indian School in South Dakota. He also served as disciplinarian and choir instructor. In November, Professor Wheelock, as he was often referred to, resigned to take the musical director position at Haskell Institute in Lawrence, Kansas, the largest Indian school in the west. His major task was to organize and prepare an Indian band for the 1904 St. Louis World’s Fair. At Haskell, he was also in charge of the orchestra and mandolin club. In early January, his new band gave a concert in the chapel. In late January 1903, the Wheelocks suffered another tragedy, the death of their baby boy Leland shortly before his first birthday. He was buried in the Haskell cemetery. A baby girl, Louise Frances, arrived in April to brighten their lives.

That month a listing of Haskell Institute band members included four familiar names because they later became Carlisle football stars. A fifth, Robert Bruce, aka Nagiyanpe, had played in the Carlisle Indian School band and led the town band. After getting the Haskell band in shape, Wheelock scheduled a tour from June 1 to December 24 of the following year. According to The Daily Gazette, over a million people heard them play in a five-week summer tour of Colorado resorts.

In April 1904, Dennison closed a contract with the World’s Fair to have a two-week engagement instead of the expected one week. His band was to play in connection with another band for three of the concerts. Lawrence Daily World reported:

“There is great rivalry for this contest, which it virtually is, and each band will play its best. Mr. Wheelock does not know what band he will have to play with. There is trouble in band circles over the playing there of Sousa and Innes, just before Mr. Wheelock’s band comes. These men are great rivals and personal enemies and trouble is expected when either one attempts to direct the other band. Under the rules when the two bands play together the bandmasters take alternate turns at leading. This is where the trouble is expected to start.” No such altercations were reported as having happened.

It went on to say that Wheelock had closed a contract for touring the country for five years, for which he would receive $23,000 a year plus railroad fares. Because of the band’s reputation, the lyceum bureau believed it would make good wherever it went.

The Haskell Band was an instant success at the St. Louis World’s Fair in June, reputedly drawing larger crowds than Sousa had drawn. After finishing their two-week engagement, the band toured the country, playing at Philadelphia, Cleveland, Indianapolis, Chicago and other musical centers, returning later in the season for another World’s Fair engagement. It even gave two concerts at Mt. Holly Park, near Carlisle, Pennsylvania during the tour.

The Carlisle band did not appear in St. Louis, likely because Superintendent was being retired around this time as punishment for statements he had made about the Bureau of Indian Affairs during a speech he gave at the Baptist convention. The fair’s resident band was from Chilocco Indian School, home of the model government Indian school exhibit’s director.

In late September, Dennison signed a four-year contract with Slayton Lyceum Bureau to make tours of the United States and Europe. Wheelock’s United States Indian Band, as it was then called, toured much of the country until mid-December when Wheelock disbanded his band for the winter and returned to his home in Lawrence, Kansas. Within days he was organizing a new band at Haskell. His plan was to build another all-Indian band, drill it until he left on tour, and hand it over to another instructor at the school.

In mid-March, he brought his family back to De Pere, where he intended to make it his future headquarters. By late April, band members were gathering at Steinway Hall in Chicago and doing “…some unusually hard work for a few weeks before going out on their concert tour.”

While in Fort Wayne, Indiana on the tour, Dennison shared this nugget with a reporter:

“The writing of music is one of the most uncertain occupations in which one can engage. Like the prospector who digs the soil in the hope of discovering hidden gold, the composer of music writes and writes and endeavors, in some instances, for years in the hope of striking a chord that will meet with popular approval.” He continued opining on the topic for several minutes more.

In late July, Louisa wrote a friend that, although she was still in Wisconsin, she intended on joining Dennison while he was on tour in the east. She related that her little daughter Louise had learned to speak the Oneida language and insisted on speaking it to everyone, including her Chippewa mother.

Dennison became ill with consumption (tuberculosis) in August and sold his interest in the band to his brother James. A Chicago specialist treated him for a few weeks and told him to spend the winter in Arizona. If he went, he didn’t stay long because he was back in Wisconsin by spring. He was apparently not idle during his convalescence because he was working as an attorney in November 1906. He had reputedly been studying under Pennsylvania lawyer John R. Miller.

So, Dennison Wheelock did not leave Carlisle in 1900 to practice law and invest in real estate. So, that all started nearly seven years later.