On Monday, The Colorado Chautauqua honored Black entrepreneur Oliver Toussaint Jackson — known as O.T. Jackson — by hanging framed photos of the first manager of Chautauqua Dining Hall, near the entranceway of the very building where he supervised a staff of 75 in 1898.
While the tribute was done in celebration of Black History Month, the images will remain permanently on display to pay homage to the businessman — a son of former slaves — who played a significant role in not only the beginning stages of Chautauqua, but in the Front Range’s culinary scene, local government, Black-based independent homesteading and community development within Colorado.
“Jackson was the most prominent African-American Boulder citizen of his day, yet his accomplishments and legacy are not generally known,” said Dan Corson, historian and board member of The Colorado Chautauqua Association.
While in graduate school at University of Colorado Denver, Corson took a course on Colorado history and chose “The Black Community in Boulder, Colorado” as his term paper topic in 1996.
Through extensive research he learned about the all-Black area of Boulder, known as the Little Rectangle — a section of the Goss-Grove neighborhood, that contained homes built by former slaves. Jackson — who moved to Boulder in 1892 and had established himself as a successful restaurateur several years before taking the job at Chautauqua — lived several blocks north of the area at 2228 Pine St.
“There have been some articles in recent years focusing on Jackson and other early prominent African-American residents,” Corson said. “However, in the wonderful 1981 history of Chautauqua entitled ‘The Grand Assembly,’ the interesting fact that the first manager of the Chautauqua Dining Hall was an African-American — in an era in which African-Americans were generally relegated to manual labor — is not mentioned.”
At Chautauqua’s July 4th opening in 1898, over 4,000 people visited and were served a dinner that included strawberries with cream.
Jackson’s efforts extended far beyond making sure guests of Chautauqua enjoyed fresh culinary delicacies in the summer.
In 1910, he established Dearfield — an all-Black agricultural community about 25 miles south of Greeley.
But, it wasn’t founded without a fight.
The state land office repeatedly ignored Jackson’s requests. Eventually, with the help of then-Colorado Gov. John F. Shafroth — for whom he worked as a messenger — Jackson successfully obtained land for his colony.
Jackson worked as a governor’s messenger for two decades.
“The governor’s staff was small in those days so the messenger interacted with other state departments by delivering messages between them and the governor’s office,” Corson said. “A messenger had to be very discreet and trustworthy. The job duty also included some office management.”
In addition to owning his home on Pine Street, Jackson honed his farming skills on a farm he purchased outside of Boulder, in 1894, that he owned for 16 years.
“O.T. Jackson is a fascinating character,” said Shelly Benford, Chautauqua’s chief executive officer. “He wasn’t just a successful entrepreneur, the first manager of the Chautauqua Dining Hall and a major player in Colorado’s state government, which would be enough for one person. He also founded Dearfield, Colo., following the advice of Booker T. Washington to ‘Get a home of your own. Get some property…get some of the substance for yourself.’ He invested his own money to buy land and created a successful self-sufficient, all-Black agricultural colony in Weld County that would likely be there today if not for the Dust Bowl. I would love to have known him.”
Dearfield — that earned its name for being “a land so dear to its settlers” —included a school, two churches, shops, a gas station and its own post office.
Residents raised a range of crops and livestock, including melons, squash, corn, hay, sugar beets, alfalfa, turkeys, chickens and ducks.
The settlement became a getaway destination for Blacks who lived in the Mile High City. At the week’s end, many would board a train that would take them to the community — approximately 70 miles northeast of Denver — where they would enjoy live music in the dance hall, fish the South Platte River, hunt and even attend rodeos.
At the height of the colony in 1919, there were several hundred Black people farming and operating businesses on 20,000 acres.
In 1995, after an 11-year crusade started by U.S. Sen. Hank Brown, Dearfield was finally listed on the National Register of Historic Places.
Jackson owned and operated a popular seafood restaurant at 55th and Arapahoe called Jackson’s Resort at the same time he worked at the Chautauqua Dining Hall. The eatery — where Boulder’s Dinner Theatre (BDT Stage) sits now — remained a lucrative venture and a consistently frequented establishment until its closure with the arrival of Prohibition in 1907.
“Jackson started in the catering business when he was 14,” Carson said. “His parents, former slaves from Virginia, were in that business in Oxford, Ohio, where he was born. Jackson never stopped engaging in new careers or new aspects of his restaurateur career. He seemed to be full of ideas and made them real, which would have been quite a struggle for an African-American in that era.”
From opening up an ice-cream parlor and an oyster bar to running a full catering company and managing The Stillman Hotel and Café, located where The Kitchen restaurant now stands, Jackson greatly enriched the local economy and community.
“Despite these crucial contributions, the lives of many important Black Americans are rarely mentioned in history classes, making it incumbent upon those of us who know about these contributions to recognize them, promote them and express our gratitude for them,” Benford said.
Corson has previously worked with Historic Boulder to outline walking tours of homes and sites of early African-American citizens throughout Boulder. He is currently collaborating with the organization to create an app that would allow interested participants to embark on self-guided tours on foot, on bike or in a vehicle.
For now, visitors can enjoy a meal at the Dining Hall and take in the historic photographs of an inspiring leader whose expansive legacy lives on.
“We especially wanted to pay homage this year because CCA board member Dan Corson had brought his research on the contributions of O.T Jackson to our attention,” said Liza Purvis, Chautauqua’s director of marketing and communications. “Honoring the diversity of Chautauqua’s personnel and visitors is more important to us than ever given recent national events.”
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