Appalachian Community Histories – Winona, Montgomery County: Railroads, Cotton Mills, Fires, and Fannie Lou Hamer
In the rolling hills of north-central Mississippi, the city of Winona grew from a railroad settlement into one of the region’s important commercial and political centers. Long before automobiles and interstate highways reshaped travel across the state, trains brought merchants, farmers, laborers, and visitors through a town whose streets, hotels, and businesses developed around the railroad tracks. Its position between the Mississippi Delta and the eastern portion of the state helped establish Winona as a trading center, while its selection as the county seat of Montgomery County in 1871 gave the growing community an importance that extended beyond transportation.
The history of Winona, however, reaches far beyond the railroads that made it prosperous. The community experienced destruction during the Civil War, rebuilt following devastating fires, developed a cotton and textile economy, and became part of the struggle over political rights and racial equality in Mississippi. Its downtown buildings preserve evidence of nineteenth-century commercial ambition, while photographs taken in 1911 reveal the difficult working conditions experienced by families employed in the local cotton mills.
During the twentieth century, Winona also became associated with events that influenced the American Civil Rights Movement. In June 1963, Fannie Lou Hamer and several other activists were arrested and brutally beaten in the Montgomery County jail after a confrontation at the town’s bus station. Hamer’s account of the violence reached a national audience the following year and helped expose the dangers faced by African Americans seeking equal citizenship.
Together, these events reveal a town shaped by opportunity, industry, hardship, and conflict, whose history reflects many of the larger transformations experienced throughout Mississippi and the American South.
Before Winona: The Land and Its Early Communities
The region surrounding present-day Winona was part of the ancestral homeland of the Choctaw people long before the establishment of Montgomery County or the arrival of the railroad. The Treaty of Dancing Rabbit Creek, signed in 1830, transferred vast areas of Choctaw territory to the United States and accelerated the removal of Choctaw communities westward, although some Choctaw families remained in Mississippi. The land opened to expanding American settlement subsequently became part of an agricultural economy supported by farms, plantations, and the labor of enslaved African Americans.
Before Montgomery County was established, the land on which Winona would develop belonged to Carroll County, while territory farther east was administered as part of Choctaw County. Carroll County’s antebellum economy relied heavily on agriculture and slavery, with the 1860 federal census recording more enslaved residents than free inhabitants. The history of the area before Winona’s founding therefore includes not only the movement of settlers and merchants but also the experiences of enslaved people whose labor contributed to the development of the surrounding countryside.
Several smaller settlements existed in the region before Winona emerged as a commercial center. Among these were Middleton and Lodi, communities whose histories became closely connected with the railroad’s arrival. The 1994 National Register nomination for the Winona Commercial Historic District, drawing upon the locally published Winona Centennial, 1861–1961, identifies Middleton as a settlement about two miles east of Winona and Lodi as a community approximately thirteen miles farther east.
As Winona began attracting businesses and residents, people from these older communities relocated to the developing railroad town. The historical account describes Lodi as having transferred much of its population and commercial activity to Winona during the town’s earliest years, illustrating how a new transportation route could change the economic fortunes of an established settlement.
The Mississippi Central Railroad and the Founding of Winona
Winona’s development began around 1860 with the arrival of the Mississippi Central Railroad, a north-south transportation route that connected communities across the state and offered access to markets well beyond the surrounding countryside. Railroad construction encouraged the establishment of commercial centers at convenient stopping places, and Winona soon attracted merchants, travelers, and residents seeking the advantages of a growing railroad community.
The origins of the town’s name remain somewhat uncertain. Local histories have traditionally associated the name with the family of Colonel O. J. Moore, whose land became part of the original settlement. The 1994 National Register documentation acknowledges this tradition but cautions that the exact circumstances surrounding the naming of Winona have not been conclusively established.
The developing town was situated along the Mississippi Central tracks, with Front Street becoming the principal commercial thoroughfare. Summit Street extended westward from the railroad, establishing the general arrangement that would define Winona’s downtown for generations. Commercial buildings faced toward the trains, reflecting the railroad’s importance to the community’s economic life.
By 1861, Winona had begun developing the institutions and businesses necessary to support a permanent population. Its location encouraged travel and trade, while the surrounding farms supplied agricultural products that could be shipped by rail. Yet the settlement had little opportunity to enjoy uninterrupted growth before the outbreak of the American Civil War.
The Civil War and the Destruction of the Railroad
The American Civil War interrupted Winona’s development almost as soon as the community had been established. Mississippi’s secession in 1861 placed the young railroad town within the Confederacy, and the transportation route that had encouraged its growth became strategically important to both Confederate and Union military forces.
According to the historical account preserved in the Winona Commercial Historic District nomination, the community contributed two companies of soldiers to the Confederate cause. The departure of local men, disruption of business, and destruction associated with military operations created severe difficulties for a town that had barely begun developing its commercial identity.
The Mississippi Central Railroad was especially vulnerable because of its importance in moving soldiers, equipment, and supplies. Union forces repeatedly targeted railroad facilities throughout Mississippi in an effort to weaken Confederate transportation and communication. The National Register account reports that Winona’s railroad depot was burned during a Federal cavalry raid in 1864 associated with Benjamin Grierson’s operations.
The war also devastated nearby communities. Middleton, already losing population and commercial activity to Winona, reportedly suffered destruction during a Federal raid. By the war’s conclusion in 1865, Winona had lost much of its early commercial development, and the town faced the challenge of rebuilding damaged businesses and transportation facilities.
The collapse of slavery also fundamentally changed the social and economic structure of the surrounding countryside. Emancipation brought legal freedom to African Americans who had previously been enslaved, although the struggle for economic independence, political participation, and equal treatment would continue for generations.
Reconstruction offered Winona an opportunity to recover, but rebuilding required more than replacing destroyed structures. The railroad had to be restored, businesses needed customers and capital, and residents had to adjust to the changed political and economic circumstances of the postwar South.
The Establishment of Montgomery County in 1871
One of the most important developments in Winona’s early history occurred in 1871, when the Mississippi legislature created Montgomery County from portions of Carroll and Choctaw counties. The Winona Commercial Historic District nomination identifies May 13, 1871, as the date associated with Winona becoming the county seat, although the original legislative act remains the best authority for confirming the precise legal chronology.
The decision reflected the growing importance of railroad communities during Reconstruction. Throughout Mississippi, the development of new towns encouraged changes to older county boundaries, allowing local government to operate closer to expanding population centers. Winona’s railroad access and growing commercial activity made it an advantageous location for the new county government.
As the county seat, Winona became the center of local administration, court proceedings, property records, and political activity. Farmers and residents from the surrounding countryside traveled into town not only to buy supplies or ship agricultural goods but also to conduct business involving taxes, land transactions, and legal matters.
The establishment of Montgomery County strengthened Winona’s influence over nearby communities, including Duck Hill and Kilmichael. Its commercial reach also extended into neighboring Carroll County, where residents from Carrollton and Vaiden participated in the regional economy.
The new county was racially diverse from its earliest years. The Mississippi Encyclopedia reports that the 1880 federal census recorded 6,671 white residents and 6,677 African American residents in Montgomery County, an almost equal division that reflected the importance of African American families to the region’s agricultural workforce and developing communities.
Winona’s growth during Reconstruction was therefore connected to two developments occurring simultaneously. The railroad and county government expanded the town’s economic opportunities, while emancipation and the subsequent struggle over political and economic power transformed the lives of the people living within its boundaries.
The Great Fire of 1888 and the Rebuilding of Downtown
During the decades following the Civil War, Winona developed into an increasingly active commercial center. Merchants established stores along the streets surrounding the railroad, while agricultural production in Montgomery County created a steady demand for warehouses, transportation services, equipment, and financial institutions.
A description of Winona in 1866, reproduced in the National Register historical documentation, identified a variety of businesses and professional services, including hotels, boarding houses, a livery stable, a drugstore, millinery establishments, a photography gallery, physicians, and attorneys. Such enterprises demonstrate how quickly the community began recovering from the destruction of the war.
This period of growth suffered a serious setback in 1888, when a disastrous fire destroyed much of Winona’s downtown business district. The loss was particularly significant because commercial buildings represented both private investments and the infrastructure necessary to support the town’s wider trading region.
Residents nevertheless began rebuilding, and the resulting construction helped establish the architectural character that survives in parts of downtown Winona. Brick commercial buildings became especially prominent, replacing many of the earlier structures that had been vulnerable to fire.
The July 13, 1888, edition of The Winona Times, quoted in the National Register documentation, described ambitious plans for new industries and commercial establishments, including a cotton compress, brick factory, ice factory, hotel, stores, and residences. The report reflected a determination among local business leaders to transform disaster into an opportunity for continued expansion.
By the early 1890s, Winona supported banks, a developing public library, and additional industrial enterprises. The Winona Brick and Tile Company, established around 1890, employed approximately thirty to forty workers according to the period accounts reproduced in the historic district nomination.
The rebuilding of downtown was not the last time fire threatened the community. Another destructive blaze damaged Winona’s business district in 1904, requiring further rebuilding and demonstrating the continuing vulnerability of crowded commercial areas during the period.
Although these fires changed the appearance of downtown, they also contributed to the collection of late nineteenth-century and early twentieth-century commercial buildings that later became important to Winona’s historic preservation efforts.
The Crossroads of North Mississippi
Winona’s role as a transportation center expanded significantly in 1889, when the Columbus and Greenville Railroad intersected the Illinois Central Railroad, formerly the Mississippi Central, at the town. The junction provided east-west connections to complement the existing north-south route, strengthening Winona’s position as a regional center for passengers, agricultural shipments, and commercial trade.
This development helped establish the nickname “Crossroads of North Mississippi,” a description that reflected the town’s position within an expanding transportation network.
The importance of the railroad remains visible in historic maps and photographs. Sanborn fire insurance maps preserved by the Library of Congress document Winona in 1886, 1889, and 1905, providing detailed evidence of the changing arrangement of businesses, streets, and industrial buildings.
The 1886 edition consisted of a single sheet, while the 1905 edition expanded to six sheets, reflecting the greater area and complexity of the town’s developed environment. These maps recorded structures for insurance purposes, but they now provide historians with valuable evidence of how Winona changed during its most important period of commercial expansion.
Historic postcards preserved by Mississippi State University Libraries offer another view of the community. A photograph of Front Street postmarked in February 1910 shows the railroad depot, commercial buildings, utility poles, and horse-drawn wagons along an unpaved street. Another postcard from March 1911 captures railroad cars and surrounding commercial activity, preserving a town in the midst of changes brought by industrialization and modern transportation.
These images reveal how closely railroad operations and everyday business were connected. The depot stood near the center of commercial life, while stores, hotels, and warehouses developed around the movement of freight and passengers.
As Winona prospered, transportation became more than a means of reaching distant markets. It shaped where people worked, which streets attracted businesses, and how residents understood their community’s place within Mississippi.
Cotton, Agriculture, and the Farmers’ Alliance
Although railroads encouraged the growth of Winona, agriculture remained central to the economy of Montgomery County. Cotton production, grain cultivation, and livestock raising supported local families and generated the trade that flowed through the town’s commercial district.
The Mississippi Encyclopedia describes Montgomery County as an important center of Mississippi’s agricultural economy during the late nineteenth century. In 1880, approximately 73 percent of county farms were operated by their owners rather than tenants or sharecroppers, a comparatively high proportion for the postwar state.
Landownership, however, was not equally distributed across racial lines. By 1900, approximately two-thirds of white farming families in Montgomery County owned their land, compared with only about one-fifth of Black farmers. These differences reflected the economic inequalities that continued to shape opportunities after emancipation.
Winona also participated in the agricultural reform movements of the period. In 1888, the Mississippi Farmers’ Alliance established a cooperative store in town to help members purchase supplies and market their crops. The organization sought to address financial difficulties experienced by farmers, including burdensome credit arrangements and the economic influence of merchants and lenders.
The agricultural movement also found a voice in Winona’s newspaper industry. In 1888, Dr. Wilson Alexander Hurt established The New Farmer, a weekly newspaper associated with the Farmers’ Alliance. Preserved issues document discussions of agriculture, political reform, farm management, and the problems facing rural communities.
The Library of Congress identifies the newspaper as an important source for understanding Mississippi’s late nineteenth-century agrarian movement. Its pages included correspondence from farmers, reports of Alliance meetings, agricultural advice, and advertisements for farm equipment and household goods.
In 1890, The New Farmer merged with other publications to form The Mississippian, but its brief period of publication left behind evidence of a time when Winona served as a center for agricultural organization as well as commercial trade.
Winona Cotton Mills and the Lives of Industrial Workers
By the beginning of the twentieth century, Winona’s economy extended well beyond agricultural trade. Cotton processing, textile manufacturing, sawmills, brickworks, and other enterprises provided employment and helped establish the town as an industrial center within its region.
An article published in Southern Field in August 1904, summarized in the National Register nomination, described Winona as an attractive location for manufacturing and noted the presence of cotton mills, cotton compresses, oil mills, sawmills, stave mills, brickworks, and an ice plant.
The town’s industrial development created new opportunities for wage employment, but it also introduced difficult working conditions for laborers and their families. These conditions were documented in 1911 when photographer Lewis Wickes Hine visited Winona as part of his work for the National Child Labor Committee.
Hine traveled throughout the United States photographing children employed in factories, mines, mills, and other workplaces. His photographs were intended to expose the realities of child labor and support efforts to improve labor protections.
During his visit to Winona in May 1911, Hine photographed textile workers, mill housing, and families whose livelihoods depended upon employment at the Winona Cotton Mills. These photographs, now preserved by the Library of Congress, provide some of the most revealing primary evidence of everyday life in the town during the industrial era.
One photograph shows members of the Dickerson family, whose children worked in the cotton mill while their father was employed in a machine shop. Hine recorded the mother’s statement that the children together earned twelve to fourteen dollars each week. His accompanying notes raised questions about the necessity of employing the younger children and the economic circumstances of the household.
Another photograph documents the McFarland family, in which a widowed mother and her sons worked in the cotton mill while a daughter remained at home to manage household responsibilities. Hine’s caption stated that the youngest boy had already been employed at the mill for five years.
His photographs also show workers leaving the mill and the houses of the surrounding mill village. Together, these images reveal how industrial employment shaped entire households, including children whose labor contributed to their families’ incomes.
The photographs are especially important because they preserve experiences that were often overlooked in local promotional histories. While commercial publications praised industrial growth and expanding payrolls, Hine’s work documented the workers whose labor made such development possible.
Winona’s cotton mills therefore represent both the prosperity associated with industrial expansion and the social difficulties experienced by working families in the early twentieth-century South.
Hotels, Churches, and the Architecture of a Growing Town
As Winona became an established railroad and commercial center, its built environment expanded to accommodate travelers, businesses, and a growing residential population. Hotels became particularly important because railroad passengers and traveling salesmen frequently needed lodging while conducting business in town.
Among the community’s notable historic buildings was the Wisteria Hotel, constructed in 1910. Designed by R. H. Hunt and Company, the hotel featured an imposing wooden structure with galleries that originally extended around portions of the building. Its architecture reflected the importance of accommodations during the height of passenger railroad travel.
The Hotel Simmons, constructed in 1927, further demonstrated the demand for lodging and commercial hospitality. Traveling salesmen often used hotels as temporary business headquarters, displaying merchandise and arranging meetings with local merchants.
A surviving register from the Winona Hotel provides direct evidence of this activity. Preserved by the Mississippi Department of Archives and History, the register records guests between June and December 1919, including information about their residences, rooms, and arrival times. The document provides a glimpse into the movement of people through Winona during the years when railroad travel remained essential to business.
Religious and residential architecture also reflected the community’s development. Churches, substantial private residences, and public buildings appeared along Summit Street and surrounding neighborhoods, creating a townscape that combined commercial activity with civic and religious institutions.
Historic properties such as Immanuel Episcopal Church, the James C. Purnell House, and the residence associated with Congressman Thomas Upton Sisson preserve evidence of the architectural tastes and social institutions of Winona’s late nineteenth-century and early twentieth-century residents.
The town’s historic buildings are important not simply because of their appearance but because they illustrate the different functions of a growing regional center. Commercial buildings served customers and merchants, hotels accommodated travelers, churches supported congregations, and residences reflected the changing fortunes of local families.
Winona During the Great Depression and New Deal
By the 1930s, automobiles and improved roads were beginning to change transportation throughout Mississippi, although railroad passenger service remained an important part of Winona’s economy.
The National Register documentation cites a 1930 account reporting that ten Illinois Central passenger trains and four Columbus and Greenville Railroad trains passed through Winona daily. The same account described a town with an active cotton mill, an ice plant, cotton gin, lumber businesses, newspaper, and other commercial enterprises.
Like communities throughout the country, Winona experienced the economic uncertainty associated with the Great Depression. Contemporary promotional accounts continued to emphasize the town’s industrial and commercial advantages, but such descriptions should be understood as evidence of local optimism rather than proof that the community escaped the hardship of the period.
Federal public works projects also contributed to the town’s development. In 1932, construction of the United States Post Office on Summit Street provided Winona with a new federal building. The National Register documentation identifies the structure as the first federal building constructed in Montgomery County and connects its construction to federal efforts to support employment during the early Depression.
Another important development was the Winona Community House, constructed through the Works Progress Administration. On July 2, 1935, the Winona City Council voted to apply for federal assistance for the project, and the building was completed in July 1936.
The community house was designed in a Tudor Revival style, with stone walls, prominent gables, and decorative features resembling traditional European architecture. Its construction reflected the New Deal effort to provide public facilities while creating employment during the Depression.
These buildings remain important reminders of a period when federal investment helped reshape civic life in small American communities.
Segregation and Organized Resistance to Civil Rights
Winona’s twentieth-century history cannot be separated from the racial segregation that shaped life throughout Mississippi. Although the town had developed commercial institutions, schools, churches, and public facilities, African American residents faced laws and practices that restricted their political rights and access to public accommodations.
Following the United States Supreme Court’s 1954 decision in Brown v. Board of Education, which declared racial segregation in public education unconstitutional, white segregationist organizations expanded throughout Mississippi in opposition to desegregation.
Winona became involved in this movement through the Association of Citizens’ Councils of Mississippi. According to historian Stephanie R. Rolph, writing for the Mississippi Department of Archives and History, the statewide association was organized in October 1954 and operated out of Winona.
The association coordinated local Citizens’ Council chapters and promoted political campaigns intended to preserve segregation. Its activities included supporting a proposed constitutional amendment that would permit Mississippi to close public schools rather than comply with federal desegregation requirements.
Citizens’ Councils frequently relied upon economic and political pressure to discourage African Americans from participating in civil rights organizations. Black residents who challenged segregation risked losing employment, credit, housing, or other resources controlled by influential white citizens.
The association’s presence in Winona demonstrates how a relatively small community could serve as a center for a statewide political movement. It also provides important context for understanding the hostility that civil rights activists encountered when they passed through Montgomery County during the following decade.
Fannie Lou Hamer and the Winona Jail Beatings of 1963
One of the most nationally significant events associated with Winona occurred on June 9, 1963, when civil rights activist Fannie Lou Hamer and several companions were arrested following a stop at the town’s bus station.
Hamer had been born in Montgomery County on October 6, 1917, before her family moved to Sunflower County during her childhood. Raised in a sharecropping family, she became involved in the Civil Rights Movement in 1962 after attending a meeting concerning African American voter registration.
Her involvement quickly brought threats and retaliation. After attempting to register to vote, Hamer lost her employment and housing on the plantation where she had worked, but she continued organizing alongside members of the Student Nonviolent Coordinating Committee.
In June 1963, Hamer and a group of fellow civil rights workers were returning to Mississippi from a voter education workshop in South Carolina. Their Continental Trailways bus stopped in Winona, where several members of the group entered the bus station restaurant.
Among those traveling with Hamer were Annell Ponder, June Johnson, Euvester Simpson, Rosemary Freeman, and James West. Some entered the restaurant while others attempted to use the restroom, placing them in conflict with the racial segregation enforced at the facility.
According to Ponder’s sworn affidavit, members of the group sat at the lunch counter normally reserved for white customers. A police officer and highway patrolman entered and ordered them to leave, despite federal restrictions on racial discrimination in interstate transportation facilities.
The activists complied with the order but began documenting what had happened. When Ponder attempted to record the license plate number of a patrol vehicle, officers arrested members of the group. Hamer, who had remained aboard the bus for much of the encounter, was also taken into custody after attempting to determine what had happened to her companions.
The arrests led to a terrifying experience inside the Montgomery County jail.
In sworn statements preserved by the Civil Rights Movement Veterans project, Hamer and Ponder described severe beatings carried out by law enforcement officers and other prisoners acting under their direction. Fifteen-year-old June Johnson was also assaulted, while Ponder suffered injuries during repeated beatings and interrogations.
Hamer described being forced into a cell where two Black prisoners were ordered to beat her with a weighted leather weapon. When one man became exhausted, another was instructed to continue. Hamer attempted to protect an area of her body previously weakened by childhood polio, but she suffered serious injuries that affected her health for the remainder of her life.
Her account provides firsthand evidence of the violence rather than a later interpretation of the incident. Hamer’s testimony describes not only the physical assault but also the threats, humiliation, and fear experienced by the prisoners.
Civil rights organizer Lawrence Guyot later traveled to Winona in an attempt to help secure the group’s release. He was arrested and beaten as well.
After several days in custody, the activists were released. They soon learned that Medgar Evers, Mississippi’s NAACP field secretary, had been assassinated outside his Jackson home on June 12, 1963.
The Winona incident demonstrated how ordinary acts, including attempting to eat at a bus station restaurant or documenting police conduct, could expose African Americans to arrest and violence during the segregation era.
The Federal Trial and Hamer’s National Testimony
The violence in Winona did not remain a purely local matter. Federal authorities investigated the incident, and in December 1963, the Winona police chief and Montgomery County sheriff faced federal charges connected with the treatment of the civil rights workers.
The proceedings took place in Oxford, Mississippi, where an all-white jury acquitted the officers. The outcome illustrated the difficulty of obtaining legal accountability for racial violence in Mississippi during the early Civil Rights Movement.
Yet the events in Winona continued to influence the wider struggle for political equality.
On August 22, 1964, Fannie Lou Hamer appeared before the Credentials Committee of the Democratic National Convention in Atlantic City, New Jersey. Representing the Mississippi Freedom Democratic Party, she challenged the exclusion of African Americans from the state’s regular Democratic political organization.
During her testimony, Hamer recounted her efforts to register to vote, the retaliation she had faced, and the violence inflicted upon her in Winona.
Her testimony connected the denial of voting rights with the dangers faced by people who attempted to exercise their citizenship. Rather than discussing discrimination as an abstract political problem, Hamer described the consequences that ordinary African Americans experienced when they challenged segregation.
The hearing reached a national television audience and helped establish Hamer as one of the most recognizable voices of the Civil Rights Movement.
Winona’s name consequently became associated with an event that exposed the brutality of segregation to people across the United States. The town that had once gained recognition as a transportation crossroads now occupied a place in the national history of voting rights and the struggle for racial equality.
Local Journalism and the Continuing Struggle for Change
The years following the Winona jail beatings brought continued controversy over civil rights, public accountability, and the desegregation of local institutions.
An important source for this period is the surviving collection of records from WONA, Winona’s local radio station, preserved by the Mississippi Department of Archives and History.
WONA began broadcasting in October 1958 under the management of Robert A. Chisolm. Its news programming covered city government, public meetings, criminal investigations, and other matters affecting Winona and the surrounding counties.
Chisolm and Hembree Brandon, editor of The Winona Times, became involved in efforts to report on the activities of local government and public school officials. Their reporting sometimes provoked opposition from people who believed that the coverage placed local officials or institutions in an unfavorable light.
Following WONA’s reporting on controversial matters, including the Winona bus station incident, a group of local officials and residents filed a complaint with the Federal Communications Commission. The complaint challenged the station’s conduct, but federal investigators ultimately rejected the allegations against WONA in February 1965.
The station’s surviving records also document discussions of school desegregation, federal antipoverty programs, local government decisions, and disputes involving public officials during the 1960s.
As Montgomery County confronted federal desegregation requirements, WONA and The Winona Times sought information about school board meetings, including meetings conducted without advance public notice. Their reporting provides evidence of the continuing debate over the responsibilities of local government and the public’s right to know how decisions were being made.
These records demonstrate that the Civil Rights Movement in Winona did not end with the release of Hamer and her companions. Questions about education, political authority, economic opportunity, and equal protection continued shaping public life throughout the following years.
Historic Preservation and the Legacy of Winona
The physical history of Winona remains visible in its historic commercial buildings, residences, churches, and civic landmarks. Although transportation patterns and commercial activity changed considerably during the twentieth century, the arrangement of downtown streets still reflects the railroad-oriented settlement that emerged in the nineteenth century.
In 1994, the Winona Commercial Historic District was documented for the National Register of Historic Places. The district recognized the importance of transportation and commerce to the community’s development, particularly between 1888 and 1941.
The historical study emphasized how Winona’s downtown grew around the railroad depot and developed into a center for merchants, hotels, banks, and other businesses. It also recognized the architectural importance of buildings constructed following the town’s destructive fires.
A broader Winona Historic District was listed on the National Register on June 1, 2015. According to the Mississippi Department of Archives and History, the district encompasses portions of downtown and neighboring residential areas, including commercial, governmental, educational, religious, and residential properties.
Its recognized period of historical significance extends from 1862 to 1965, reflecting more than a century of changes in the town’s built environment.
Original photographs, newspaper collections, maps, and government records provide additional ways to understand this history. The Sanborn fire insurance maps reveal changes in commercial development, Mississippi State University’s postcards document everyday streets and buildings, and Lewis Hine’s photographs preserve the lives of industrial workers who might otherwise have received little attention in published town histories.
Records from the Montgomery County courthouse, the Works Progress Administration historical research collections, and WONA’s surviving broadcasts further demonstrate the value of preserving local evidence.
For Winona, historical preservation involves more than recognizing old architecture. It also requires understanding the people who lived and worked in the town, including merchants and railroad employees, farmers and factory workers, African American families struggling for political equality, and individuals who challenged the injustices of their time.
Why Winona’s History Matters
Winona’s history illustrates how transportation could transform a small settlement into an important regional center. The arrival of the Mississippi Central Railroad created the foundation for the town, while the establishment of Montgomery County gave it political importance. The railroad junction of 1889 encouraged commerce and industry, and the town’s surviving buildings reflect the growth that followed.
Yet the history of Winona cannot be understood solely through its railroad, commercial success, or architectural landmarks. Its prosperity depended upon the labor of people whose experiences were not always celebrated in early accounts. Cotton farmers, factory workers, and children employed in textile mills helped sustain the economy, while African American residents continued struggling against political and economic inequalities long after emancipation.
The violence inflicted upon Fannie Lou Hamer and other civil rights workers in June 1963 represents one of the darkest chapters in the community’s history, but it also connects Winona to a national movement that challenged segregation and transformed American democracy.
Today, the town’s historical record contains both the achievements of a developing railroad community and the evidence of those who endured hardship or challenged injustice within it. Preserved buildings, original maps, newspaper accounts, photographs, and firsthand testimony make it possible to examine those experiences together.
Winona’s story is therefore not simply one of railroad development or commercial growth. It is the history of a Mississippi community that experienced the Civil War, Reconstruction, industrialization, agricultural reform, segregation, and the Civil Rights Movement, leaving behind a record that continues to illuminate the wider history of the American South.
Sources & Further Reading
Appalachian Regional Commission. “Appalachian Counties Served by ARC.” https://www.arc.gov/appalachian-counties-served-by-arc/
Dittmer, John. Local People: The Struggle for Civil Rights in Mississippi. Urbana: University of Illinois Press, 1994. https://www.press.uillinois.edu/books/?id=p065071
Hamer, Fannie Lou. “Fannie Lou Hamer Interview: Winona, Mississippi.” Interview transcribed March 17, 1964. Student Nonviolent Coordinating Committee Digital Gateway. https://snccdigital.org/wp-content/uploads/digitalcollections/63_flh_winona.pdf
Hamer, Fannie Lou. “Remarks of Mrs. Fannie Lou Hamer from the Proceedings of the Democratic National Convention Credentials Committee.” August 22, 1964. Lyndon Baines Johnson Library, National Archives. https://docsteach.org/document/hamer-dnc/
Hamer, Fannie Lou. “Sworn Affidavit of Fannie Lou Hamer Regarding Police Brutality in Winona, Mississippi.” June 1963. Reproduced in Mississippi Black Paper, 1965. Civil Rights Movement Veterans. https://www.crmvet.org/nars/aff/mbp_flh.htm
Hine, Lewis Wickes. “The Dickerson Family, Dependent Parents.” Photograph, May 1911. National Child Labor Committee Collection, Library of Congress. https://www.loc.gov/item/2018676458/
Hine, Lewis Wickes. “Going Home, Winona (Miss.) Cotton Mills.” Photograph, May 1911. National Child Labor Committee Collection, Library of Congress. https://www.loc.gov/item/2018676456/
Hine, Lewis Wickes. “The McFarland Family, Winona Mississippi Cotton Mills.” Photograph, May 1911. National Child Labor Committee Collection, Library of Congress. https://www.loc.gov/item/2018676460/
Johnson, June. “Sworn Affidavit of June Johnson Regarding Police Brutality in Winona, Mississippi.” June 1963. Reproduced in Mississippi Black Paper, 1965. Civil Rights Movement Veterans. https://www.crmvet.org/nars/aff/mbp_jj.htm
Larson, Kate Clifford. Walk with Me: A Biography of Fannie Lou Hamer. New York: Oxford University Press, 2021. https://academic.oup.com/book/38828
Larson, Kate Clifford. “Writing a Woman’s Trauma.” Women’s History Network, 2021. https://womenshistorynetwork.org/writing-a-womans-trauma-by-kate-clifford-larson/
Library of Congress. “New Farmer (Winona, Miss.).” Chronicling America: Historic American Newspapers. https://www.loc.gov/item/sn88067115/
Mills, Kay. “Fannie Lou Hamer: Civil Rights Activist.” Mississippi History Now, April 2007. Mississippi Department of Archives and History. https://mshistory.mdah.ms.gov/issue/fannie-lou-hamer-civil-rights-activist
Mississippi Department of Archives and History. “James C. Purnell House.” Historic Resources Inventory. https://www.apps.mdah.ms.gov/Public/prop.aspx?id=23999&view=facts
Mississippi Department of Archives and History. “Montgomery County Records, 1873–1913.” Series 2050, County Records. Archival Finding Aids. https://finding.mdah.ms.gov/government-records/mont
Mississippi Department of Archives and History. “Winona Commercial Historic District.” National Register of Historic Places Nomination, 1994. https://www.apps.mdah.ms.gov/nom/dist/141.pdf
Mississippi Department of Archives and History. “Winona Community House.” National Register of Historic Places Nomination. https://www.apps.mdah.ms.gov/nom/prop/24011.pdf
Mississippi Department of Archives and History. “Winona Historic District.” National Register of Historic Places, listed June 1, 2015. https://www.apps.mdah.ms.gov/Public/district.aspx?id=256&view=facts
Mississippi Department of Archives and History. “The Winona Hotel (Winona, Miss.) Register.” Manuscript Collection Z/1916, 1919. https://finding.mdah.ms.gov/manuscripts/z1916000
Mississippi Department of Archives and History. “Wisteria Hotel.” Historic Resources Inventory. https://www.apps.mdah.ms.gov/Public/prop.aspx?id=23898&view=facts
Mississippi Department of Archives and History. “WONA Radio Station (Winona, Miss.) Records.” Manuscript Collection Z/1990, records dating from the 1960s. https://finding.mdah.ms.gov/manuscripts/z-1990000
Mississippi Encyclopedia. “Montgomery County.” Center for the Study of Southern Culture, University of Mississippi. https://mississippiencyclopedia.org/entries/montgomery-county/
Mississippi State University Libraries. “Front Street, Winona, Mississippi.” Historical postcard, 1910. Lucius Marion Lampton Historical Images Collection. https://scholarsjunction.msstate.edu/mss-lampton-images-ms-delta/244/
Mississippi State University Libraries. “Hotel Simmons, Winona, Mississippi.” Historical postcard, 1940. Lucius Marion Lampton Historical Images Collection. https://scholarsjunction.msstate.edu/mss-lampton-images-ms-delta/254/
Mississippi State University Libraries. “Mississippi Newspapers on Microfilm.” Special Collections, including The Winona Times, 1884–1978. https://www.library.msstate.edu/specialcollections/collections/miss/newspapers
Mississippi State University Libraries. “Scene at a Cotton Gin, Winona, Mississippi.” Historical postcard, 1910. Lucius Marion Lampton Historical Images Collection. https://scholarsjunction.msstate.edu/mss-lampton-images-ms-delta/11/
Mississippi State University Libraries. “Street Scene, Winona, Mississippi.” Historical postcard, March 11, 1911. Lucius Marion Lampton Historical Images Collection. https://scholarsjunction.msstate.edu/mss-lampton-images-ms-delta/12/
Mississippi State University Libraries. “Wisteria Hotel, Winona, Mississippi.” Historical postcard. Lucius Marion Lampton Historical Images Collection. https://scholarsjunction.msstate.edu/mss-lampton-images-ms-delta/386/
National Park Service. “Winona Commercial Historic District.” National Register of Historic Places, NRIS 94000659, July 1, 1994. https://npgallery.nps.gov/AssetDetail/NRIS/94000659
Ponder, Annell. “Sworn Affidavit of Annell Ponder Regarding Police Brutality in Winona, Mississippi.” June 1963. Reproduced in Mississippi Black Paper, 1965. Civil Rights Movement Veterans. https://www.crmvet.org/nars/aff/mbp_ap.htm
Rolph, Stephanie R. “The Citizens’ Council.” Mississippi History Now, October 2019. Mississippi Department of Archives and History. https://mshistory.mdah.ms.gov/issue/the-citizens-council
Sanborn Map Company. Sanborn Fire Insurance Map from Winona, Montgomery County, Mississippi. January 1886. Library of Congress, Geography and Map Division. https://www.loc.gov/item/sanborn04542_001/
Sanborn Map Company. Sanborn Fire Insurance Map from Winona, Montgomery County, Mississippi. August 1889. Library of Congress, Geography and Map Division. https://www.loc.gov/item/sanborn04542_002/
Sanborn Map Company. Sanborn Fire Insurance Map from Winona, Montgomery County, Mississippi. February 1905. Library of Congress, Geography and Map Division. https://www.loc.gov/item/sanborn04542_005/
Smithsonian Institution. “Fannie Lou Hamer’s Dauntless Fight for Black Americans’ Right to Vote.” Smithsonian Magazine, 2020. https://www.smithsonianmag.com/history/fannie-lou-hamers-dauntless-fight-for-black-americans-right-vote-180975610/
Student Nonviolent Coordinating Committee Digital Gateway. “Beatings in Winona Jail.” Duke University and the SNCC Legacy Project. https://snccdigital.org/events/beatings-winona-jail/
Author Note: Winona’s history reveals how railroads, industry, and the people who built a community shaped the development of north-central Mississippi. From its historic downtown to the experiences of Fannie Lou Hamer and other civil rights activists, this article preserves the stories of a town whose influence extended far beyond Montgomery County.