Top 15 Charming Small Towns to Explore in Mississippi

The state with a name so lengthy that many children learn a brief song to accurately spell it, Mississippi is also the home to one of the longest rivers in the United States – the aptly titled Mississippi. Abundant in Native American, Spanish, and French history, Mississippi experienced a relatively late development in the context of the U.S., ultimately preserving a distinctive blend of these markedly different cultures. The river’s bluffs and the verdant interior harbor hidden treasures – small towns steeped in history, characterized by Southern hospitality and an invitingly relaxed lifestyle.

Indulge in home-cooked meals, art, quality music, and natural beauty while exploring our curated list of the 15 best small towns to visit in Mississippi.

1. Cleveland, Mississippi

Cleveland is situated in Bolivar County, named after the South American political figure, Simon Bolivar. The town itself is accessible off Route 61 and was named to honor former U.S. President, Grover Cleveland. Established by individuals relocating from the Mississippi River to the Delta, Cleveland now boasts a robust local economy and a thriving music culture.

Two Mississippi Blues Trail markers reside in town: Christmas Street, formerly a center for African-American life and commerce, and the blues musician W. C. Handy. For blues enthusiasts, the GRAMMY Museum Mississippi is a must-visit. The Martin & Sue King Railroad Museum is also located in Cleveland. Savor some Southern comfort cuisine at the Country Platter or indulge at Fat Baby’s Catfish House.

2. Oxford, Mississippi

Oxford is a collegiate town located in Lafayette County, home to the well-known University of Mississippi, colloquially referred to as “Ole Miss.” Established on land that originally belonged to the Chickasaw until the treaty of Pontotoc Creek, the founders purposively named the town Oxford with the intent of creating a center of knowledge in the Southern U.S. This aspiration materialized when the state legislature designated Oxford as the location for the new state university in 1841. In more recent history, the first presidential debate of 2008 occurred at Ole Miss.

After exploring the campus, take a leisurely walk at Lamar Park or visit the historic Confederate Cemetery. Enjoy a hike through Bailey’s Woods or gather delights at the Midtown Farmers Market. Experience music at Lyric Theatre before savoring a delightful meal at the Ravine. For accommodation, treat yourself to relaxation at the charming The Nests BnB!

3. Bay St. Louis, Mississippi

Situated in Hancock County, Bay St. Louis is positioned on the upper Gulf Coast, conveniently near New Orleans. With its historical architecture and scenic open spaces, infused with Southern charm, the town successfully rebounded from Hurricane Katrina, restoring its artistic and eclectic character that distinguishes it.

Stroll through the shops on Main Street to find that perfect piece of art for your home at Central Hall, or walk to the beach at the end of Main Street. Enjoy breakfast at the Buttercup or sip coffee at Mockingbird Cafe – it’s a great place to connect with locals! Experience relaxation at Carroll House Bed and Breakfast during your stay!

4. New Albany, Mississippi

New Albany, located in Union County, developed around a grist and sawmill on the Tallahatchie River, subsequently becoming a vibrant river port. Its growth was interrupted during the Civil War when Union troops destroyed much of the town. However, New Albany revitalized upon the introduction of the railroads in the 1880s and is notable as the birthplace of celebrated American writer William Faulkner, who was born in 1897.

Discover New Albany’s flourishing neighborhoods and preserved historic areas. Rent a bike and enjoy some exercise along the Tanglefoot Trail, then treat yourself to a delicacy from Sugaree’s Bakery. High Point Coffee Roasters is also a short distance away for a caffeine boost, or if hunger strikes, George’s Restaurant is the perfect spot for fried chicken! Experience Southern hospitality at the Concord Inn and recharge away from urban pressures.

5. Corinth, Mississippi

Corinth, located in Alcorn County, was initially named Cross City when it was established in 1853. The name was later changed to Corinth, inspired by a suggestion from a newspaper editor, reflecting the town’s role as a railroad crossroads similar to the ancient Greek city. During the Civil War, Confederate General Beauregard retreated to this area after the Battle of Shiloh, with the Union army eventually besieging Corinth in a tactic known as “the Siege of Corinth.”

Corinth is an ideal destination for history enthusiasts; visitors can tour the Veranda House, which served as a headquarters for Confederate generals during the Civil War, as well as the Siege and Battle of Corinth sites and Fort Williams. Relish an old-fashioned soda at Borroum’s Drugstore and Soda Fountain, followed by a hearty meal of barbecue at the Rib Shack. Experience history firsthand and enjoy comfort at the General’s Quarters Inn.

6. Ocean Springs, Mississippi

Situated in Jackson County, Ocean Springs was the first permanent French outpost, Fort Maurepas, established in French Louisiana to counteract Spanish encroachment. Subsequently named Ocean Springs, this area capitalized on the natural springs and has since evolved into a resort community.

Ocean Springs continues to embrace its artistic resort atmosphere. The downtown area, revitalized after Hurricane Katrina, is adorned with oak trees, galleries, and boutique shops. Seafood is a local staple, revered by residents and contributing significantly to the economy. Stroll along the Fontainebleau Nature Trail or Front Beach before heading into town for local seafood at Mikey’s on the Bayou. Your stay at The Inn at Ocean Springs promises comfort, making it difficult to leave!

7. Vicksburg, Mississippi

As the county seat of Warren County, Vicksburg is positioned on a bluff overlooking the Mississippi River, directly across from Louisiana. The French explorers were the first European settlers to inhabit this region, founding Fort Saint Pierre in 1719. Vicksburg played a crucial role during the Civil War, notably during the Siege of Vicksburg, which was a pivotal moment that granted the Union Army complete control of the Mississippi River.

Explore this historical town and take advantage of the Vicksburg National Military Park, which preserves the narrative of this significant site. Additionally, the Old Courthouse, a historic gem, merits your attention. Browse the exhibits at H.C. Porter Gallery and wander through the scenic Linden Plantation Gardens. After a day of exploration, enjoy dinner with a view at 10 South Rooftop Bar and Grill before retreating for the night at the quaint Anchuca Historic Mansion and Inn.

8. Natchez, Mississippi

Natchez, located in Adams County, serves as the county seat and sits across the Mississippi River from Vidalia, Louisiana. Originally, the area was occupied by the Natchez Native Americans before French colonists arrived, subsequently ceding the land to the Spanish following the French and Indian War. Due to its strategic position on the bluff overlooking the Mississippi and its rich history, Natchez was designated as the first capital of Mississippi, until the more contemporary city of Jackson usurped this title later on.

Tour Natchez and traverse a section of the Natchez Trace, an exquisite pathway through the forest historically utilized by the Natchez people. Visit the Auburn Museum and Historic Home or indulge in a delightful Southern Carriage Tour! Satisfy your sweet craving at Cotton Alley Cafe or experience lunch at the Camp Restaurant. Unwind at the Monmouth Historic Inn at Natchez and temporarily escape the demands of daily life.

9. Port Gibson, Mississippi

Port Gibson is situated in Claiborne County and was formerly part of “La Louisianne” during the era of French dominance. Following the Louisiana Purchase, the territory transitioned to the United States, and the area became populated by plantation owners who introduced African slaves after displacing the local Native Americans. The blues genre surged in popularity in the 20th century with the establishment of the Rabbit’s Foot Company, which is recognized on the Mississippi Blues Trail.

Experience local cuisine at Rosie’s Cafe before checking into Isabella B&B. During your visit, explore the Grand Gulf Military Park, where camping is an option for nature enthusiasts. Stroll through the downtown area, adorned with historic mansions and murals that honor Port Gibson’s resilient history. You will understand why it is famously referred to as “the town that was too beautiful to burn” during the devastation of the South towards the end of the Civil War.

10. Ridgeland, Mississippi

Located adjacent to the Ross Barnett Reservoir, Ridgeland sits in Madison County. The town was originally conceived by two developers from Chicago, Edward Treakle and Gordon Nichols, who acquired the land and initiated a marketing campaign to entice Northerners to relocate to a southern utopia.

Thanks to this campaign, Ridgeland was the birthplace of Faith Hill, who lived here until the eighth grade. Rent a bike and explore the Ridgeland Bike Trail or traverse the Natchez Trace. Treat yourself to a delightful seafood dining experience at Seafood R’evolution, or savor a steak at Shapley’s Restaurant. Unwind with some pampering at the Hyatt and enjoy a moment of relaxation.

11. Holly Springs, Mississippi

Holly Springs is located in Marshall County, Mississippi, right on the border with Tennessee. Historically dotted with cotton plantations established on land seized from the Chickasaw Native Americans, the town served as a supply depot for Union General Grant during the Civil War, particularly during the siege of Vicksburg.

Explore the Strawberry Plains Audubon Center or enjoy the scenic Wall Doxey State Park, and don’t forget your camera! Immerse yourself in nature at the Holly Springs National Forest or visit the Ida B Wells Museum, which honors the famous activist born here. Delight in comfort food at Southern Eatery and experience relaxation at Court Square Inn Bed & Breakfast.

12. Canton, Mississippi

Canton resides in Madison County, near the state capital of Jackson. A significant portion of the town is listed on the National Registry of Historic Places, and one of its notable landmarks is the historic Canton Courthouse. Additionally, Canton hosts a large Confederate cemetery; it acted as a shipping and logistics hub during the Civil War, providing care for many wounded soldiers.

Canton holds historical significance on the Mississippi Blues Trail – renowned blues artist Elmore James honed his craft here. Several famous juke joints flourished on Hickory Street, which continues to showcase these landmarks. Wander through Hickory Street to discover these points of interest, and be sure to visit the majestic courthouse in the square full of shops. Extend your stay at Heart’s Content Bed and Breakfast and relish your time in this unique town.

13. Carthage, Mississippi

Nestled in Leake County, Carthage was named after the hometown of the Harris Family (early settlers) in Tennessee. In the mid-20th century, Carthage gained some recognition by hosting a “Tri-Racial Goodwill Festival” for whites, African Americans, and Native Americans but faced racial tensions during the Civil Rights Movement.

Carthage has moved beyond those challenges, and visitors should explore downtown and discover a unique spot – Rustic Flair. Enjoy breakfast at The Bakery and Cafe or savor delicious seafood at Penn’s Seafood. Carthage offers a welcoming atmosphere, making it a great place for a brief visit or a longer stay.

14. Tupelo, Mississippi

Located in the northern region of the state, between Memphis, Tennessee and Birmingham, Alabama, Tupelo is situated in Lee County and is recognized as the birthplace of Elvis Presley! Named for the tupelo trees (commonly referred to as black gum) surrounding it, Tupelo was originally called Gum Pond by early settlers. French and Spanish explorers arrived here, trading with locals; however, following U.S. expansion, all Native Americans were subsequently relocated as more settlers moved westward.

While visiting the town, take the time to explore the Battle of Tupelo site, a significant Civil War event. Additionally, visit Elvis Presley’s Birthplace and Museum, as well as the Elvis Presley Center! Experience vibrant dining at Kermit’s Outlaw Kitchen or enjoy some fried chicken at Connie’s Fried Chicken, before resting at Moon Lake Farm Bed and Breakfast after your culinary adventure.

15. Wiggins, Mississippi

Wiggins is situated in Stone County and was named after Wiggins Hatten, one of the initial homesteaders in the region. The town thrived for a period, supporting lumber mills and various businesses until a mysterious fire destroyed over half of it in 1910. Since then, Wiggins has rebuilt and is ready to welcome visitors.

Make a visit to Wiggins and discover G&M Goat Farm, a local establishment creating its own products, including goat soap! If you’re visiting in the summer, cool off at Flint Creek Water Park before taking a leisurely stroll down Historic Pine Street. Delight in fresh pastries at Daily Fresh Donuts or dine at Whistle Stop Cafe. For a serene experience, extend your stay at the Peacock Bed and Breakfast and enjoy the tranquility.