The African American Cheshire Country Club: Connecticut’s Overlooked Pioneer of Black Leisure
- Richard Smith
- Feb 21
- 4 min read
Updated: Mar 11
In the summer of 1917, at the height of the Jim Crow era and amid the turbulence of World War I, a remarkable institution took root along the trolley line between New Haven and Waterbury. The Cheshire Country Club—founded, owned, and operated by African Americans—opened its doors on 22 acres along what is today Route 70, near Mountain Road.
Long overshadowed in national narratives by the Shady Rest Country Club, the Cheshire Country Club predates it by four years. Established in July 1917 and boasting 200 members by October of that same year, the club stands as one of the earliest documented African American country clubs in the United States—and quite possibly the first of its kind.
The Setting: An 18th-Century Landmark Reimagined
The clubhouse itself was a striking blend of colonial heritage and modern recreational ambition. The
structure, built circa 1785, was a mid-18th-century clapboard residence featuring:
Original 24-light windows with early sash and frames.
A substantial central chimney characteristic of colonial construction.
Traditional wood clapboard siding.
A broad veranda extending across the front façade and along one side.
Set back approximately 150 feet from the road on a slight terrace, the house overlooked a well-kept lawn that created a dignified approach from the New Haven–Waterbury trolley line. The location made it easily accessible to visitors traveling from major urban centers.
Inside, the main entrance opened directly into a spacious parlor or ballroom—the social heart of the club. This room hosted dances, card parties, musical evenings, and formal receptions. The building was thoughtfully arranged to accommodate its new purpose, including:
A dedicated billiard room.
Auxiliary rooms for private gatherings and administrative use.
Ample space for formal dinners and large assemblies.
The historic home was transformed into a refined social center without sacrificing its architectural character.
Johnson L. Haile: The Visionary Founder
The driving force behind the club was Johnson Leroy Haile (1865–1923), a respected figure in Waterbury’s Black community. Haile had worked as head waiter at the Scoville House Hotel and served as steward to philanthropist Harriet B. Thorpe. His career in elite hospitality exposed him to the structure and culture of private clubs—institutions that systematically excluded African Americans.
In January 1917, Haile purchased the 22-acre property from Minnie S. Stanwood. Within months, he had established a country club that provided Black professionals, entrepreneurs, and families with something exceedingly rare: a dignified recreational sanctuary free from racial exclusion.
Haile’s life had earlier drawn sensational headlines after a disfiguring acid attack by a former companion—an incident widely reported at the time. Despite personal adversity, he emerged as a determined entrepreneur whose legacy would reshape Connecticut’s social landscape.
A National Membership in Its First Season
The club’s rapid growth was extraordinary. By October 1917, only months after opening, the Cheshire Country Club counted 200 members from across the nation, including Washington, D.C., Knoxville, Tennessee, Massachusetts, and New York.
Coverage in leading African American newspapers—including The New York Age and The Chicago Defender—described the club in vivid detail. Reports emphasized that it was owned and managed entirely by and for African Americans, distinguishing it from white-owned venues that occasionally allowed limited Black access. The club quickly became a magnet for the Black professional class of the Northeast.
Recreation, Refinement, and Community
The Cheshire Country Club was designed to rival white country clubs in both elegance and activity.
Its amenities included:
Golf: A five-hole golf course was integrated into the 22-acre grounds. While modest in size compared to larger courses, it represented an extraordinary achievement for an African American institution in 1917. In 1929, members even competed for the Cockburn Trophy against golfers from Shady Rest.
Tennis: Professionally maintained tennis courts provided another venue for athletic competition and social engagement.
Social Events: The club’s calendar featured Labor Day clambakes drawing over 300 attendees, formal dances with live music, and card parties.
In August 1931, the club hosted a formal dinner for Judge James S. Watson of New York, one of the state’s earliest Black judges and an attorney associated with Marcus Garvey. Such events reinforced the club’s status as a center of intellectual and professional exchange.
Leadership and Governance
Though located in Cheshire, the club was deeply connected to Waterbury’s Black leadership. Its Board of Governors included Dr. P. F. Anderson, Dr. B. B. Costa, Col. Fabian McKinney, and James E. Kefford, a leading figure in the Waterbury Negro Business League. These men represented the growing economic strength of Black professionals in Connecticut. The club was not merely recreational; it was a statement of self-determination and economic cooperation.
Correcting the Historical Record
For decades, Shady Rest in New Jersey has been widely cited as the first African American country club, founded in 1921. Yet Cheshire’s documented operation beginning in July 1917 places it firmly earlier in the historical timeline. The club’s prominence in Black newspapers of the era confirms that it was not a small, obscure experiment, but a celebrated institution within African American society.
Later Years and Transition
After the deaths of key leaders—including Haile in 1923 and Kefford in 1940—the club gradually declined. By the 1930s, it remained active but was occasionally rented for corporate outings, such as a 1933 event hosted by the U.S. Rubber Company.
Sometime in the 1940s or 1950s, the institution ceased operating as an African American country club. For a period, it was run as Mitchell’s Country Club (or the J.Q. Mitchell Club). In 1946, they featured entertainers such as M.C. Buddy Taylor and a floor show including blues singer Edith Washington, Dorothy Profit ("Miss Hype Hips Herself"), and "Ole Red Fox," the Connecticut comedy cut-up who kept the audience in stitches. Harold "Gabby" Allen of Ansonia also often appeared there.
The historic building eventually transitioned into commercial use and became widely known to Cheshire residents as the Colonial Package Store at 871 West Main Street, near the “Notch” on Route 70. It later briefly housed other businesses before its eventual demolition. Today, the intersection of Mountain Road and West Main Street shows little physical evidence of the groundbreaking enterprise that once stood there.
Enduring Significance
The Cheshire Country Club was far more than a golf course and dance hall. It was a declaration of economic independence and a cultural sanctuary in an era of segregation. Though the building is gone, its legacy remains embedded in Connecticut’s landscape and in the broader history of African American entrepreneurship. Long before the better-known clubs of the 1920s, a 22-acre terrace in Cheshire quietly made history.
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