The small, picturesque towns that fill Mississippi are by far one of the state’s best assets. From quaint downtown areas to significant historical sites, these tiny towns are often full of surprises, along with a whole lot of charm. Since visiting every small town in Mississippi would take quite some time, we picked 10 of the most charming and planned a road trip around them. At just under 14 hours, the trip is perfect for a weekend getaway. So buckle up and get ready for more charm than you could’ve every imagined!

1. Bay St. Louis

As one of "America’s Coolest Small Towns," Bay St. Louis is a great way to start off your road trip. Home to just over 10,000 residents, the small coastal community is known for a trendy downtown area, filled with great shops and eateries.

2. Ocean Springs

Nestled on the state’s coastline, Ocean Springs definitely delivers when it comes to scenic beauty, but that’s not all it has to offer. As the oldest city in the state, Ocean Springs is proud of its heritage. The perfect mix of old and new, the beachside town is loaded with history along with great restaurants, shops, galleries, and more.

3. Bay Springs

Tucked away in Jasper County, just over 2,000 residents are lucky enough to call Bay Springs home. Visit during the holiday season and you’ll be in for a real treat, as the picturesque small town looks even more perfect thanks to city-wide Christmas displays.

4. New Albany

When it comes to things to do, this small town is definitely not lacking. Its location on the Tallahatchie River means fishing opportunities are practically endless; not to mention there’s a beautiful downtown area that's known for its great shopping, especially when it comes to antiques. New Albany is also the starting point of one of the state’s longest Rails to Trails paths,

the Tanglefoot Trail.

5. Holly Springs

Dating back to the Civil War, this small town is known for its gorgeous antebellum homes, most of which are available for touring. While in Holly Springs, you’ll definitely want to visit the famous Phillips Grocery – "home of the country’s best burger." There’s plenty more to see in the charming town, including the Strawberry Plains Audubon Center, Chewalla Lake Recreation Area, and a national forest.

6. Oxford

Unlike any other city, Oxford offers big city culture while retaining a small town vibe. Throughout the years, the city, which is often referred to as the "cultural Mecca of the south," has been recognized numerous times, landing spots on lists, such as the "Best Small Towns in America" and "Best College Towns."

7. Cleveland

This "hip little town in the Mississippi Delta," is definitely a must visit. Aside from the only Grammy Museum outside of Los Angeles, you’ll find plenty of fun in Cleveland, especially in the form of festivals and events. From farmers markets to annual events, like Art in the Alley, the vibrant town has definitely earned its spot on Smithsonian Magazine’s list of "Small Towns To Visit."

8. Port Gibson

Located between Vicksburg and Natchez, Port Gibson has a population of less than 2,000. As legend has it, the small town’s beauty is what led General Grant to spare it during the Civil War, claiming it was "too beautiful to burn." Even though Port Gibson is most known for being home to the Windsor Ruins, it has much more to offer, including gorgeous architecture of yesteryear, old-fashioned storefronts, battlefields, and historically significant Civil War sites.

9. Natchez

This picturesque river city is filled with beautiful historic homes, a charming downtown area, variety of restaurants and quaint shops, and river walks, perfect for taking in views of the Mighty Mississippi.

10. Woodville

Tucked away in the southwest corner of the state, Woodville is by far one of Mississippi’s best kept secrets. The small town has a lot of history and even more charm; not to mention it’s home to one of the best outdoor recreation areas in Mississippi, the Clark Creek Nature Area.

Looking for another great road trip idea? Check out "The Christmas Lights Road Trip Through Mississippi That’s Nothing Short Of Magical."