An interior view of the Ground Zero Blues Club in Clarksdale, Mississippi. Editorial credit: Jacque Manaugh / Shutterstock.com.

8 Of The Most Eccentric Towns In Mississippi

From American music history to epic architectural marvels, these small towns in Mississippi have a story to tell. In a state with such diverse topography and rich heritage, it is no surprise that several cities are ideal for a day trip. There is a lot to do and see, including the birthplace of the King of Rock and Roll, the birthplace of the Delta Blues, and the icon of American culture.

Mississippi is known for more than just its musical heritage, though. Many places still retain Antebellum architecture, such as Port Gibson, a town that General Ulysses S. Grant called "too pretty to burn." Exploring heritage and musical trail markers and discovering public murals along the way are just a couple of reasons to visit these quirky towns, which leave a fun and historical impression on their visitors.

Clarksdale

An exterior view of the Delta Blues Museum in Clarksdale, Mississippi.
An exterior view of the Delta Blues Museum in Clarksdale, Mississippi. Editorial credit: Jacque Manaugh / Shutterstock.com.

Clarksdale is famously known as the birthplace of the blues, and legends such as Muddy Waters and Sam Cooke are associated with it. The blues reverberate throughout the entire community, which features live music seven days a week. Before you head to a show at one of the juke joints, visit the Delta Blues Museum to learn about this historic American music and Clarksdale's contributions.

Self-guided tours are recommended and will lead you through the Arts and Culture District. The vibrant area with colorful buildings is home to museums like the Tennessee Williams Rectory Museum and several galleries such as Hambone Art and Music. Local artist Stan Street operates the latter, which is becoming a landmark in this eccentric and fun town.

Port Gibson

Windsor ruins in Port Gibson, Mississippi
Windsor ruins in Port Gibson, Mississippi.

General Ulysses S. Grant famously regarded Port Gibson as "too pretty to burn" during the Vicksburg Campaign of the Civil War. One cannot drive through town without stopping at the Windsor Ruins, one of the most iconic sites in Mississippi. The 23 Corinthian columns once supported the massive Windsor Plantation, which was destroyed by fire in 1890.

The A.K. Shaifer House is a historic home that served as a Union hospital during the Civil War. Today, it is open to the public, featuring walking trails and signs that detail its significance. The quaint downtown area is part of the Main Street Program due to its walkability, shops, and restaurants, such as the Royalty Lounge and Bistro. It is also home to elegant inns such as the Isabella Bed and Breakfast.

Flora

Entrance to the Mississippi Petrified Forest in Flora, Mississippi.
Entrance to the Mississippi Petrified Forest in Flora, Mississippi. Image credit Chad Robertson Media via Shutterstock

Flora is a small, family-centric community with interesting sites and fun festivals held throughout the year. Its landmark feature is the Mississippi Petrified Forest, which formed from a log jam that occurred millions of years ago. It makes for a pleasant walk where the scent of honeysuckle vines and wildflowers fills the air. A trail leads past a national landmark denoting a 36-million-year-old trunk. It also has access to the Earth Science Museum, which includes fossils and dinosaur teeth on display.

Visiting Flora during one of the annual festivals, such as the Harvest Festival, is an excellent time to meet the friendly locals and learn more about this area. You can also spend time with the community at one of the fantastic eateries, such as the Blue Rooster or Annie M's Cafe. Flora is a great day trip location with eccentric sites, some of the best in the state.

Leland

Painted wall in honor of old Mississippi Bluesmen in Leland.
Painted wall in honor of old Mississippi Bluesmen in Leland. Image credit Pierre Jean Durieu via Shutterstock

The small town of Leland is situated on the banks of Deer Creek inside the historic Mississippi Delta. It is also the birthplace of Muppets creator Jim Henson and is affectionately known as "the birthplace of Kermit the Frog." Jim Henson's Delta Boyhood Exhibit is a landmark that the Blue Ribbon Travel Show named "Best Mississippi Museum" because it attracts over 10,000 visitors annually. The Delta region also has strong ties to the Blues, and the Leland Blues Project was created by the Leland Historical Foundation to "honor the Mid-Mississippi Delta Blues artists and educate the public on their contributions to music and influence on the world."

The Highway 61 Blues Museum is downtown, surrounded by several downtown murals that pay homage to the birthplace of the Blues. The community takes pride in its musical legacy. It hosts the annual Highway 61 Blues Festival in conjunction with the museum, providing one of the best times to experience the significance of this small town to American culture.

Crystal Springs

An oversized tomato sculpture in Crystal Springs, Mississippi.
An oversized tomato sculpture in Crystal Springs, Mississippi. Image credit Jimmy Emerson via Flickr.

Crystal Springs, once known as the "Tomato Capital of the World," is a friendly community with a rich agricultural heritage. It is now a Main Street Community for its traditional downtown area and community events, including the Downtown Holiday Market, Taste of the Blues, and, of course, the Tomato Festival.

The historic downtown features cultural attractions, including the Robert Johnson Blues Museum, honoring the "Grandfather of the Blues," and the J. T. Biggs, Jr. Memorial Library. It's also a fun town to explore on foot. The vibrant area is accented with teal-colored awnings and giant tomato statues, adding a quirkiness to this sleepy Mississippi town.

Water Valley

Water Valley Watermelon Carnival, Water Valley, Mississippi.
Water Valley Watermelon Carnival, Water Valley, Mississippi. Image credit Jimmy Smith via Flickr.com

The charming Water Valley community is used to being asked, "You live where?" underscoring the town's eccentricity. It also features a classic downtown area, complete with brick storefronts and an elegant town clock. It is also home to the annual Watermelon Carnival in August, which draws more than 20,000 visitors to a town of less than 5,000 residents.

The carnival is a weekend-long event that serves as a hometown gathering for many, featuring a Street Dance, vendors, and a fireworks display at City Park. Downtown has murals depicting early railroad scenes, honoring Water Valley's roots as a lucrative stop for the Illinois Central Railroad in the 1800s. Typically Southern, Water Valley offers several classic eateries, including Courthouse Cafe and Sweet Mama's, that exemplify the town's character and friendliness.

Tupelo

The Elvis Presley Statue in Tupelo, Mississippi.
The Elvis Presley Statue in Tupelo, Mississippi. Image credit Chad Robertson Media via Shutterstock

Tupelo is most famous for being the birthplace of the "King of Rock' N' Roll," Elvis Presley. The town is filled with Elvis memorabilia, including a statue downtown, the Elvis Presley Birthplace Museum, and the Tupelo Hardware Company. The hardware store is still operating and is notable for selling 11-year-old Elvis his first guitar.

Tupelo also offers the opportunity to walk through time on its Heritage Trails and explore its cultural contributions to society. The marked trails include the Natchez Trace Parkway, Civil Rights, and a trail following the path to Shilo, Mississippi's final stand during the Civil War. The markers denote numerous historical moments that took place here, and seeing them firsthand is an awe-inspiring experience.

Natchez

A charming tourist shopping area in Natchez, Mississippi.
A charming tourist shopping area in Natchez, Mississippi. Image credit Dennis MacDonald via Shutterstock.com

The oldest city in Mississippi, Natchez, is renowned for its historic structures, including the Antebellum architecture downtown the city is known for. The best way to familiarize yourself with this charming town is by doing a self-guided Natchez Walking Tour. The tour winds through historic downtown, starting at Bluff Park and ending with a view of the river. Historic sites and museums are abundant throughout the town, each showcasing a distinct period in Natchez's rich history.

The Beulah Baptist Church is notable for its role in the Civil Rights Movement during the Parchman Ordeal in 1965. Choctaw Hall represents the elegant Greek Revival architectural style of the 1830s. Tucked between these historical structures are modern-day spas and salons, such as Anruss and Company, which bridge the past with current luxuries. The range of history, beauty, and modern conveniences lends Natchez an undeniable eccentricity.

Final Thoughts

Mississippi is a fun, historic, and culturally diverse place filled with scenic drives and eccentric towns. The Magnolia State boasts a rich musical heritage, including the birthplaces of Muddy Waters and Elvis Presley. Visitors are invited to explore their homes and museums across Tupelo and Clarksdale. These vibrant communities take pride in their culture, as evidenced by the unique finds and preserved buildings in the downtown districts.

Blues music reverberates throughout these towns, marking the birthplace of the blues, and the small communities offer many authentic blues experiences, from juke joints to annual festivals. Self-guided tours are frequently the best way to explore these small towns. However, there are also guided tours that educate visitors on the significance of a particular region or community. Whether it's arts and culture, musical heritage, or charming locales with eclectic dining options, these eight towns fit the bill.

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