In 1848, John Canfield made his inaugural foray into the Manistee region, laying the foundation for his lumber mill along the banks of the Manistee River. This pivotal endeavor heralded the dawn of Canfield's ascent to prominence within the burgeoning lumber industry. Over time, his astute stewardship propelled him to the zenith of prosperity, cementing his status as one of the region's preeminent lumber magnates.

After arriving in Manistee, John Canfield eventually grew to become one of the area’s wealthiest lumbermen.

In 1875, he started the construction of a new home designed by well-known Chicago architect William LeBaron Jenney. This vast brick mansion comprised the entire city block bounded by Fourth, Third, Cedar, and Elm Streets.

In March 1899, tragedy struck when Charles' older brother, Frank, passed away at the age of 34. Less than nine months later, his father, John, also passed away, leaving Charles the majority of the sawmill, salt and transportation operations, and the family's assets, which he shared with his mother and sisters. Charles' inheritance was estimated to be roughly $10-12 million.

In 1890, Charles tied the knot with Belle Gardner, daughter of esteemed local jeweler C.D. Gardner, in a lavish ceremony. The Manistee Advocate, on January 3, 1891, detailed the extravagant affair:

"The wedding of Charles J. Canfield and Miss Belle Gardner was a splendid event held at the bride’s parents’ residence. The parlors were adorned with holly and mistletoe, and a cascade of roses hung from the ceiling. Mrs. Murray serenaded the bridal procession with Mendelssohn’s Wedding March. After exchanging congratulations, guests enjoyed a sumptuous dinner accompanied by the Gardner family band's melodies. Mistletoe added a playful touch as young ladies coaxed gentlemen into traditional kisses. The presents, ranging from silverware to fine china, bespoke the couple’s esteemed circle of friends. The Advocate extends heartfelt wishes for their enduring happiness."

Through the decade, Charles remained entrenched in the lumbering trade, expanding into Chicago and diversifying his investments in lumber, land, and salt. Alongside Belle, they nurtured a growing family, welcoming a son and daughter into their midst.

On April, 19, 1900 the Manistee Daily News reported that work was about to start on Charles Canfield's cottage: "The house will not be a cottage so far as size is concerned, as it will be of very liberal dimensions...and will have a frontage of 72 feet. There will be broad galleries especially on the Lake side, and dormer windows will break the roof lines." The dwelling was built by Manistee contractor R.J.B. Necombe at a cost of $100,000.

With the freedom to indulge in his wealth, Charles resolved to commission a brand-new yacht for himself in 1900. Seeking the expertise of New York designer Henry Wintringham, Canfield entrusted him to craft plans for an opulent steam yacht. By early 1901, construction of the pleasure craft commenced under the skilled hands of Wilmington, Delaware boat builders, Pusey and Jones.

Approximately five months later, the extravagant yacht emerged from the shipyard, proudly bearing the name Cangarda—a fusion of its owner's surname 'Canfield' and his wife's maiden name 'Gardner'. Spanning roughly 126 feet in length, Cangarda boasted a main deck adorned with a dining room and drawing room, complemented by two single staterooms, a double stateroom, and an exclusive owner's stateroom below deck. Notably, the vessel also showcased not one, but two Tiffany skylights gracing its lower level.

Eager to embark on a maiden voyage, Canfield, accompanied by his wife and esteemed companions Robert and Kate Babcock, along with George Swigart—a lumber dealer and Canfield's business partner—and his wife, set sail on a journey to collect the yacht and return home to Manistee via the scenic route of the St. Lawrence River.

During the Cangarda's maiden voyage, troubles emerged due to excessive partying and lavish living. Belle Canfield and Robert Babcock left the trip and returned to Manistee, while Mrs. Babcock and Charles Canfield remained aboard. When they sailed the yacht into Manistee, the Canfields' and Babcocks' marriages were in disarray. Belle Canfield filed for divorce, resulting in what was reported to be the most expensive divorce in Michigan at the time.

In the aftermath, Belle received financial compensation, support for their children—Doris and Charles John (Jack)—and ownership of the Canfield Mansion in Manistee and the Canfield Cottage in Onekema, known as "The Moorings."

In the summer of 1907, tragedy struck when six-year-old Charles (Jack) Canfield passed away in Manistee, leaving Belle and Charles grieving the loss of their son.

Meanwhile, the Babcocks were also facing marital troubles. In 1904, Robert and Kate Babcock separated, but their divorce proceedings began in May 1907, finalizing in November of that year.

As speculated, on October 15, 1907, Kate Winn Babcock and Charles Canfield were married in Chicago.