The Scenic Road Trip That Leads to 5 of Mississippi’s Most Charming Small Towns

The small towns in Mississippi are some of the best in the entire country, if you ask us. Sure, we might be just a little bit biased, but we don't think anywhere can compare to the history, charm, attractions, and good old-fashioned Southern hospitality that you'll find in the Magnolia State. I love that these destinations have their own unique characters and march to their own slow-paced beats. And the pedestrian-friendly streets are icing on the cake.

If you feel the same way, you'll love the road trip we're featuring today: it'll take you to five of the cutest small towns in Mississippi. Each of these little towns would be worthy of its own day trip, so we recommend stretching this adventure out to at least three days in total if you're able to. The trip requires a little over five hours of driving time and will take you through a good portion of the state. The good news? You'll have the added benefit of getting to check out some pretty fantastic scenery and carve out time for each one. You can view the entire itinerary at Google Maps, and it's fully customizable, so feel free to add or remove stops to make the trip your own.

1. Discover the Beauty and Historical Charm of Natchez

We'll start our road trip in the beautiful walkable town of Natchez. It's right on the Mississippi River, and many of the town's attractions are within walking distance of one another, so this is a great opportunity to get out of the car and stretch your legs. It's the oldest city in the state and was once one of the wealthiest cities in America. Although Natchez is a small city with around 14,000 residents, when you're here, you'll feel small-town vibes. History buffs will find lots of inspiration here. Expect museums, historic Native American mounds, and plenty of beautiful antebellum architecture to admire. Even if you're not religious, I highly recommend paying a visit to St. Mary's Basilica. It's the oldest Catholic building in Mississippi and is an absolute work of art. And don't skip watching the warm sunsets over the mighty Mississippi - they're to die for. I have no doubt that you'll fall in love with this gorgeous town.

2. Explore Port Gibson, the Small Town "Too Pretty to Burn"

Next, we'll continue north for approximately 40 miles to Port Gibson, another historic small town. It's quite a bit smaller than Natchez, with a population of around 1,200, but there's a lot to enjoy here. There are 40 sites on the National Register of Historic Places, and the Windsor Ruins are an incredibly popular destination. These Corinthian columns are all that remain of a once-stately mansion that burned down in 1890. These iconic relics tell the story of the wealth that thrived in this historic destination. This is the kind of destination that invites you to slow down, and as you wander through the charming neighborhoods, you'll soon discover the heritage that keeps this Mississippi small town alive.

3. Uncover Ancient Trees and Nostalgic Vibes in Flora

For our next stop, we'll head to the tiny town of Flora, a suburb of Jackson with a population of around 1,600. This little town may be small, but it's a wonderful destination with plenty to check out on a visit. Flora grew up alongside the railroad, and today, it's best known as the home of the Mississippi Petrified Forest. This National Natural Landmark is incredible: it's home to 36-million-year-old trees that have turned to stone over the years, and it's an amazing spot for a hike in nature. As you stroll through this classic Mississippi small town, you'll find brick-lined streets, mom-and-pop shops, local diners, and friendly folks who make you feel like you're home.

4. Dive Deep Into Water Valley's Railroad History

You'll have to drive for about 2 hours to reach the town of Water Valley, but trust me, it's worth the effort. Like Flora, this town popped up alongside the railroad. It's now home to around 3,400 residents and is a wonderful day trip destination. You can learn about the area's railroad history at the Water Valley Casey Jones Railroad Museum. There are a lot of fun community events held here throughout the year, and the annual Watermelon Carnival attracts thousands to the town each summer. I can't get enough of the adorable town square with colorful buildings. Be sure to carve out time to stroll around the town and check out the shops. Also, you'll want to step back in time and treat yourself to ice cream or a milkshake at Turnage Drug Store, an old-fashioned soda fountain that will bring back nostalgic memories.

5. An Outdoor Playground Awaits in New Albany

Like all good things, this small-town road trip in Mississippi must come to an end, and we'll stop our journey at a great place. New Albany is a town of around 7,700 in Union County, and it's an absolute delight to visit. It's been named one of the best small towns in the South, and it's full of fun things to do, no matter where your interests lie. The bustling downtown area is full of shops and restaurants, and the city is also home to the trailhead of the Tanglefoot Trail, a 43.5-mile rail-to-trail conversion that's a perfect place to enjoy the outdoors. I love that the town is surrounded by the rolling hills of north Mississippi, making it an ideal destination for all kinds of outdoor fun.

This trip looks like so much fun; are you ready to hit the road? Make sure you check out our list of road trip snacks to keep from getting hungry along the route! And when you're feeling inspired, use Only In Your State’s itinerary planner to discover more hidden gem towns in Mississippi.