Travel Guide: The Best 5-Day Mississippi Roadtrip.

We started our Mississippi journey with one night in Jackson Mississippi, which we naturally drove into with ‘Uptown Funk’ on repeat purely for the line ‘Jackson Mississippi’, haha.

Brent’s Drugs Soda Fountain

Our first stop in Jackson was Brent’s Drugs Soda Fountain, which is a diner that opened in 1946. It’s one of the most famous diners in America and was even used in the movie, The Help!

It really is an incredible place and they do the best milkshakes!! You 100% need to visit here.

Hal & Mal’s Blues Club

We didn’t have much time in Jackson, and so we checked into the hotel and got changed, then walked over to Hal & Mal’s Blues Club.

We were in Jackson on a Monday, and Monday is the only day of the week the famous Hal & Mal’s host their Blue Monday nights.

Unfortunately Jackson celebrated St Patrick’s Day a week later than the rest of the World, and so we got to Hal & Mal’s to find it all closed up! We were devastated!! But please, if you visit Jackson, make sure you go there and tell me what it’s like?!

Eat at the random bar opposite!

A man called Donny was smoking outside a small bar across the gravel road, and called out to us, “It’s closed! They opened on the weekend for St Patrick’s instead!”

So we walked over to him to inquire further, and eventually we were persuaded to enter the bar he was sat outside.

We had nothing to lose – our destination was closed and we were hungry and thirsty!

It turned out to be THE BEST decision ever!

It was the most American bar I’ve ever been in. I ordered a club sandwich with fried okra, but I’d never had okra before so I asked the waitress what it was.

She said she didn’t like it so she yelled out to the rest of the bar, “Hey guys! How would you describe okra? They’re not from ’round here!” An older couple sat near us helped describe it “It’s goooood! Just don’t eat too much or it’ll go right through ya!”

Anyway, the club sandwich was on brioche bread and it was the best club sandwich I’ve ever had. The fried okra was pretty yummy too! We struggled to finish our food as the locals in the bar kept coming up to us and talking to us and asking us where we were from and about our journey.

But we loved every second.

Donny is a gem stone and rock expert, and drives around the country finding stones and making them into jewellery. He kindly gifted us one each!

The morning after our wild night out in Jackson, we stopped by the old Art Deco Greyhound Bus Station which was the location were many of the Freedom Riders were arrested.

We then headed to iHop and loaded up in dulce de leche pancakes iHop pancakes, eggs, bacon, and hash browns, and then drove down to Natchez via Vicksburg.

Arriving into Vicksburg

Vicksburg is a beautiful old town with a traditional American main street with wooden buildings and adorable coffee shops.

There’s often a steamboat sat on the river, and it’s home to the Biedenharn Coca-Cola Museum – aka, the place where Coca-Cola was first bottled!

National Military Park

Vicksburg is also home to the National Military Park, due to it being one of the most important sites in the Civil War.

We started off by driving around the National Military Park – it’s honestly just beautiful and we loved how lush and green it was.

After that we went into the town centre, and it was just as I remembered it!

Biedenharn Coca-Cola Museum

Last time I was here everything was closed for some reason and so we couldn’t visit the Coca-Cola Museum, but this time I finally got to visit!

In case you don’t already know, I’m a HUGE Coca-Cola fan and have collected limited edition bottles from around the world since I was 14 and first visited the World of Coca-Cola in Atlanta.

Naturally I bought a new bottle at the Biedenharn Museum (they have commemorative Biedenharn ones), and although the museum is small it’s super interesting and there are a couple of original soda fountains you can see!

Natchez Steamboat

After Biedenharn we drove down to the riverside to get a closer look at the steamboat, and then down to Natchez along the Natchez Trace Parkway – you need to drive off the highway and follow the signs for the Natchez Trace Parkway.

Trucks aren’t allowed onto the road, and it’s practically empty. It’s one of the most beautiful scenic drives and shows you the true Mississippi!

Check-in at: Monmouth Historic Inn

When we arrived in Natchez we checked-in at the stunning Monmouth Historic Inn, and made ourselves comfortable in our cute little Pond Cottage.

It was pure bliss sitting on a rocking chair in the late afternoon on the porch with a book, before heading into town for dinner at the popular local riverside restaurant, Magnolia Grill.

The next morning we headed to New Orleans for three nights, via the Oak Alley Plantation in Louisiana.

The plantation is now an organization, and one of the few plantations that actually make an effort to educate visitors on the history of slavery and the actual people who built and maintained the beautiful plantation.

We found the enslaved people’s quarter exhibition very informative, and were impressed by the plantation’s commitment to educating visitors and giving the enslaved a legacy.

For example, did you know that pecans are in commercial production because of a enslaved man named Antoine who lived at Oak Alley and was a talented botanist?

He discovered how to make a thin-shelled pecan, as they used to have very hard and thick shells that were impossible to crack!

They also have a tribute to the people who lived, worked, and died at the plantation in the form of a wall with all of the names of the enslaved on it.

As well as the huts, you can also take a tour of the beautiful big house that the enslaved people built.

The craftsmanship is magnificent, and it made me feel really sad to think that those enslaved built it by-hand for their ‘owners’ to live in.

Anyhow, the tour is well worth doing and really interesting, and I was in awe of the line of Oak Trees in-front of the building. Now I want a garden filled with old Oak trees haha!

And then it was time to head to New Orleans!! Read my guide to New Orleans!