Greenwood is a city in and the county seat of Leflore County, Mississippi, United States,[4] located at the eastern edge of the Mississippi Delta region, approximately 96 miles north of the state capital, Jackson, and 130 miles south of the riverport of Memphis, Tennessee.

The rivalry ended when Captain James Dilliard donated parcels in exchange for a commitment from the townsmen to maintain an all-weather turnpike to the hill section to the east, along with a stagecoach road to the more established settlements to the northwest.

The success of the city, founded during a strong international demand for cotton, was based on its strategic location in the heart of the Delta: on the easternmost point of the alluvial plain, and astride the Tallahatchie and Yazoo rivers.

The city served as a shipping point for cotton to major markets in New Orleans, Vicksburg, Mississippi, Memphis, Tennessee, and St. Louis, Missouri.

[7] The construction of railroads through the area in the 1880s revitalized the city;[5]: 8  two rail lines ran to downtown Greenwood close to the Yazoo River, and shortened transportation to markets.

Cotton cultivation and processing became largely mechanized in the first half of the 20th century, displacing thousands of sharecroppers and tenant farmers.

Sally Humphreys Gwin, a charter member of the Greenwood Garden Club, planted the 1,000 oak trees that line Grand Boulevard.

In 1950, Gwin received a citation from the National Congress of the Daughters of the American Revolution in recognition of her work in the conservation of trees.

[16] In memory of this event, the Mississippi Blues Trail has placed its third historic marker in this town at the site of the former radio station.

Delta Streets Academy, a newly founded private school located in downtown Greenwood, has an enrollment of nearly 50 students.

Greenwood is served by Greenwood–Leflore Airport (GWO) to the east, and is located midway between Jackson, Mississippi, and Memphis, Tennessee.