A curved highway on St Louis Bay enters land with piers on both sides.

8 Coolest Small Towns in Mississippi for a Summer Vacation

Bordered by Louisiana and Arkansas in the west and Alabama in the east, Mississippi is famous for having been a critical battleground in the 1960s fight for Civil Rights. The 20th state to join the Union is bordered to the north by Tennessee and to the south by Louisiana —as well as a spectacular 62 miles of picturesque shoreline overlooking the Gulf of Mexico's sparkling waters. Largely defined by the Gulf Coastal Plain, an area characterized by a gently-sloping terrain that includes 160 miles of maritime forests and pretty beaches, Mississippi is a stellar summer vacation destination worth exploring. For those who want to experience this slice of Southern Hospitality, this article reveals the best towns in Mississippi that can act as access points for a summer adventure.


Downtown Vicksburg near the Yazoo Diversion Canal
Downtown Vicksburg near the Yazoo Diversion Canal.

Vicksburg is enticingly curled up on top of a bluff that overlooks the Father of Waters, as the Mississippi River is known. Boasting a population of about 19,000, Vicksburg exudes a distinctive small-town charm a summer vacationer will find irresistible. For history nerds, Vicksburg was the setting of a blood-spattered siege during the Civil War that would last for 47 unforgettable days. Vicksburg was critical. Confederate President Jefferson Davis reportedly referred to it as "the "nailhead that holds the South's two halves together." The eventual surrender of Confederate forces at Vicksburg ensured Union forces now controlled the strategically important Mississippi River. Today, first-time visitors will learn much of the Town's intriguing history at the Vicksburg National Military Park, the site of the Siege of Vicksburg.

Bay St. Louis 

Archway for Bay of St. Louis Mississippi, a coastal beach town.
Archway for Bay of St. Louis Mississippi, a coastal beach town. Editorial credit: clayton harrison / Shutterstock.com

There are many reasons a summer vacationer will be interested in Bay St. Louis, the quaint little Town of about 9,000 that styles itself as "a place apart." The Town boasts several honors. In 2013, for instance, Budget Traveler ranked St. Louis among America's coolest small towns. And in that ranking, Bay St. Louis was not number 10 but an impressive position three. If 2013 is far in the past, USA Today ranked Bay St. Louis the second-best coastal small Town in the United States for 2022. Today, strolling through a street evocatively named Beach Boulevard, exploring Bay St. Louis's historic Old Town that is dotted with several 19th-century homes, and winding down at the gorgeous beach closeby, are top reasons Bay St. Louis is a summer vacationer's favorite.

Port Gibson

 The historic Claiborne County Courthouse in Port Gibson, Mississippi
The historic Claiborne County Courthouse in Port Gibson, Mississippi. Editorial credit: Chad Robertson Media / Shutterstock.com

This city of about 1,000 is the county seat of Mississippi's Claiborne County located in Southwestern Mississippi. It is nestled about 28 miles from Vicksburg. Port Gibson rests along the Natchez Trace Parkway, a 444-mile recreational road and scenic drive that cuts through the expanse of three states. For lovers of history, Port Gibson was established in 1803 and is the third oldest settlement in Mississippi. To get an idea of Port Gibson's beauty, when Union forces arrived on the scene at the height of the Civil War, General Ulysses Grant would declare the city "too beautiful to burn." Today, this cool, small Town radiates Southern warmth and charm amid an amazing collection of 19th-century architecture. It is unfathomable to visit Port Gibson without checking out the Windsor Ruins, one of the most photographed historic sites in the state.


Looking across a Riverboat Casino at the bridge crossing the Mississippi River from Natchez Mississippi to Louisiana.
Looking across a Riverboat Casino at the bridge crossing the Mississippi River from Natchez Mississippi to Louisiana.

With a population of about 13,000 and located approximately 70 miles southwest of Vicksburg, Natchez is famous for being the only city that the celebrated French aristocrat Lafayette ever visited in Mississippi. While there could be several reasons Lafayette only opted for Natchez, one speculation that might not be completely off-the-mark is the Town's beauty, including its gorgeous bluffs and its many other attractions. Known as the Biscuit Capital of the World, Natchez is hugely famous for its stunning historic homes, of which more than a thousand are listed on the National Register of Historic Places. Besides the city's fabled mansions, one factor — among others — that might have even prompted USA Today readers to place Natchez among the 10 Best Historic Small Towns in the US, Natchez also boasts several mouth-licking dining options. One of these is the Carriage House Restaurant which serves delectable Southern fare amid elegant 19th-century surroundings. 


Bologna Performing Arts Center in Cleveland, Mississippi
Bologna Performing Arts Center in Cleveland, Mississippi. Image credit: Kilobytezero, via Wikimedia Commons

Situated in the heart of the Mississippi Delta, a region that forms the most important bird migration corridor in North America and curled up beside Highway 61, mid-distant between both Memphis and Vicksburg, Cleveland has many attractions that would interest a summer vacationer. Boasting a population of about 10,000, Cleveland is the gateway to the Mississippi Blues Trail. The region that gave birth to the Blues includes fascinating markers like city streets, cotton fields, train depots, churches, and even cemeteries. Visitors to Cleveland will be happy to learn that most of these markers are within a 45-minute drive from Cleveland. Then again, the Martin and Sue King Railroad Heritage Museum, at 115 S Bayou Avenue, has railroad-related artifacts and memorabilia a vacationer can check out.


 Madison County Courthouse in Canton Mississippi USA
Madison County Courthouse in Canton, Mississippi. Editorial credit: Bennekom / Shutterstock.com

Frequently mentioned among the best small towns in Mississippi, Canton effortlessly lives up to its billing. The Town of about 10,000 is located 15 miles north of Jackson and is, therefore, conveniently close to big-city benefits. While many attractions in Canton will see a summer vacation speed away, one of Canton's most famous highlights is its historic architecture. The buildings in the courthouse square, including the Madison County Courthouse, constitute one of the finest architectural groupings in the state. Besides the square's historic architecture, anyone strolling through the square will be impressed by the charming array of quaint shops and classy restaurants that line the streets. For its beauty, Canton served as the backdrop of the movie A Time To Kill, a successful production based on John Grisham's page-turner by the same name.

New Albany

New Albany Mississippi Welcome sign located on Mississippi Highway 30
Welcome sign to New Albany, Mississippi, located on Mississippi Highway 30. Image credit: Chillin662, via Wikimedia Commons

Famous for being the gateway to the Tanglefoot Trail, New Albany is hands-down one of Mississippi's finest small towns. The Tanglefoot Trail is worth lacing up for not just because of its gorgeous scenery but also because it is the longest rail-to-trail in Mississippi. It meanders for about 43 miles through the foothills of the Appalachian Mountains — in the process cutting through dense forests, lush meadows, and marshy wetlands. First-time visitors will be excited to discover that this famous trail begins right at the heart of New Albany. But it is not just Tanglefoot Trail. New Albany is not an unknown secret. In 2017, USA Today ranked New Albany the Best Southern Small Town in the country. The magazine highlighted its vibrant downtown area that teems with eclectic art galleries, classy antique shops and boutiques, as well as stylish restaurants. 


The Stephen D. Lee House in Columbus, Mississippi, was built in 1847 by Thomas Garton Blewett.
The Stephen D. Lee House in Columbus, Mississippi, was built in 1847 by Thomas Garton Blewett. Image credit: Onasill-Bill Badzo/Flickr.

Boasting a population of about 22,000, Columbus is the birthplace of Pulitzer Prize-winning playwright Tennessee Williams. Today, the childhood home of one of the state's most celebrated literary figures serves as the Town's welcome center. Columbus is also famous for being the birthplace of Stephen Lee, the Confederate general who, by ordering the first shot at Fort Sumpter, effectively started the Civil War. Visitors can spend a meditative hour at Friendship Cemetery, where those slain during the Civil War, including four generals, lie buried. In 1866, and in this very cemetery, the Town's ladies laid flowers on the graves of the dead soldiers from both sides. This would inspire similar gestures across the nation, culminating in what is now recognized as Memorial Day.

The Takeaway

Mississippi may not be as mountainous as Colorado or Nevada, but it boasts several attractions ideal for a summer vacation. One of Mississippi's defining features is its 62 miles of picturesque shoreline overlooking the Gulf of Mexico's sparkling waters. Besides, the state lies deep in the American South, a region famous for what has come to be known as Southern Hospitality. Today, Mississippi boasts a fine collection of cool, small towns that will make a summer vacation unforgettable. Whether one will pick Bay St. Louis, Columbus, or Natchez, no one can go wrong with Mississippi's small towns.

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