Mississippi is well known for its Blues Music, Southern hospitality, great food and rich history. But did you know that you can experience all of this and more, on an epic 5-day road trip, that will take you to some of the state’s biggest highlights. Mississippi may not be the first place in the USA that you’d pick for a road trip, but take it from us, it’s often the places you least expect that end up surprising you in the best way.
We took a 5-day trip from Memphis to New Orleans, driving through the heart of Mississippi. In this guide, we are going to share our exact route, as well as all the incredible experiences to have along the way on this unforgettable, yet easy Deep South Road trip.
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Furthermore, this post is written in collaboration with Visit Mississippi who hosted us during our stay & organised many of the awesome activities we are going to share below. Therefore, a huge thank you goes out to them.
When to visit Mississippi?
The best time of year to visit Mississippi is between October-March. This is when the summer heat has subsided, and the hurricane season has passed. We visited Mississippi in late September, early October and had the most perfect weather for our entire 5-day trip. Think blue skies and 30 degrees Celsius, it was just bliss.
If that still sounds a little too warm for you, then perhaps late Winter or early Spring would suit you better. As you can expect to have cooler days this time of year. We suggest that you avoid the summer months due to extreme heat and the potential threat of hurricanes, that could disrupt your travel plans and bring stormy weather.
Where to rent a car in Mississippi?
As we mentioned previously our trip started in Memphis and ended in New Orleans, these were our pickup and drop off points. It also meant that we had the chance to drive the entire length of Mississippi, which is the route this guide will follow. We rented a car from Hertz, for the most part they were okay to deal with. As long as you have Credit Card for payment and deposit you shouldn’t experience any issues, and their drop off process was very quick and easy.
You can find most well-known global car rental agencies in the US; it really comes down to your budget and the type of car you are after. It is worth noting that for this itinerary you will not require a 4×4 for any of the listed spots. The roads in Mississippi are well maintained, as you would expect.
See the map below for the whole road trip route
Day 1-2: Touchdown in the land of the Delta Blues
If you choose to follow our same route you will start your drive South from Memphis and head towards the Mississippi Delta region. Which sits in the North-West corner of the state. This region is affectionately known as “The Most Southern Place on Earth”, because of its unique culture and history in America’s south.
Cleveland
In the heart of the Delta, you will find the charming town of Cleveland. Which is undoubtedly the best place to base yourself whilst visiting the Delta. From here you will be a stone’s throw away from some iconic historical sites and nature trails too. All of which will highlight the best of what the Delta has to offer.
Whilst you are in Cleveland you should definitely check out…
Grammy Museum Mississippi
Did you know that Mississippi is home to the most Grammy Award winning artists per capita in the whole world. The Grammy Museum in Cleveland will take you on a journey through the ages, showcasing the history of Mississippi Blues and Country music, with an interactive exhibition that gets you involved.
Inside the museum you can also compose your own songs, feel what it’s like to stand on a stage & learn about influential artists who have shaped the music industry into what it is today. The museum is certainly a highlight of any visit to the Delta region, we had so much fun in there.
Admission fee is 16USD for adults and FREE for children. More information about the museum can be found here.
Dockery Farms
This historic plantation sits just outside of Cleveland and is known as the birthplace of Blues Music. The plantation was bought in 1885 by William Dockery, he had hopes of making the land into a successful plantation, which it eventually did become. Dockery Farms is widely considered to be the birthplace of the Blues. As African American workers who would come here to cultivate the cotton fields, would play music. This in turn, hugely inspired what we know today as Blues Music.
Today, if you visit Dockery Farms, the plantation structures still stand that were built by those workers. There is also a Mississippi Blues Trail plaque, to commemorate this truly historical and groundbreaking place. Despite its historical significance, there is also a rather retro looking gas station out the front. This is a great spot to get some retro looking photos and experience a place where time has truly stood still.
Admission to Dockery Farms is FREE, and it is well worth a drive by on your way in or out of town.
Great River Road State Park
For the nature lovers, Great River Road State Park will take you right onto the shores of the mighty Mississippi River. The park is situated about a 25-minute drive West of Cleveland, just past the town of Rosedale. There are plenty of hiking trails to enjoy and bird watching is also a popular activity here.
If you visit the park in September like we did, then you will have the opportunity to witness an incredible natural phenomenon. During this time of the year the Mississippi River water levels are at their lowest and you will be able to walk out onto the riverbed for miles. Once out there it truly feels like you could be in a desert. Just make sure to take plenty of water with you.
Admission to Great River Road State Park is free as of 09/24.
Where to stay in Cleveland, Mississippi
There are plenty of options for accomodation in Cleveland from Motels to more high-end Hotels, that offer guests a more comfortable experience. We chose to stay at Cotton House, which is situated right in the centre of Cleveland. It is in a perfect location for walking around town. Their elegant rooms are equipped with all the modern comforts you would need for a great night’s sleep.
Where to eat in the Delta, Mississippi
Whilst you are in the Delta, it would be a crime to not sample some of the regions delicious cuisine. We have two recommendations for you that will plate you up a real taste of the south.
Airport Grocery – Serves authentic Delta cuisine, their menu features classics such as: Tamales, Catfish, Gravy Fries (definitely get them), Burgers and Sandwiches. All of which come with that delightful southern hospitality, in a rustic setting that will leave you thinking “wow I’m really in America now”.
Blue Levee, Rosedale – If you’re keen for a proper Deep South experience, then this soul food cafe in Rosedale is the place to be. This is a real local joint, serving soul food classics in a buffet style such as: Cornbread, Collard Greens, Fried Catfish, Southern Baked Chicken and Grits. You can tell that the food here has been made with love.
Day 2-3: Jackson, Mississippi the City with Soul
A visit to Mississippi wouldn’t be complete without checking out the capital, Jackson. The city is small and easy to visit in just one day, but it can still pack a punch into your adventure! From the outside, Jackson appears as an unassuming city. But it’s only when you start pulling back the layers and delving deeper, do you truly understand what this charming place has to offer.
On your visit to Jackson, make sure you don’t miss…
Eudora Welty House & Garden
Book lovers may have heard of Eudora Welty, she is an American novelist who wrote short stories about living in America’s Deep South. She is often referred to America’s version of Jane Austen. Eudora was born and raised in Jackson and her house still stands on a quaint suburban street within the city.
On a visit to Eudora’s House, you will get the opportunity to step inside the world of an award-winning writer. The house has been left exactly how she would have had it when she lived there. As our guide eloquently put it, it’s as though she has just stepped out for a while and will be back soon.
There is an onsite museum showcasing her work, as well as guided tours of the house that run: Tuesday-Friday at 9 and 11am, then on Saturdays at 1 and 3pm. We particularly loved admiring the garden, that has been so beautifully kept over the years. The staff at the exhibition have a wealth of knowledge about Eudora Welty and are always keen to answer any questions.
Admission to the Eudora Welty House & Garden is 10USD for adults and FREE for children. To plan your visit, you can find more information on their website.
LeFleur’s Bluff State Park
Situated just behind the Natural Science Museum, you will find the stunning Le Fleur’s Bluff State Park. The park offers walking trails, fishing spots and most importantly, you can see Cypress Trees which sit in the swamps. This was our main reason for visiting the park and it’s quite a unique experience for us as Brits.
The Cypress Trees are an iconic part of the Deep South landscape, they lay in bodies of water, usually swamps and they encompass everything we think about, when we envision the Deep South of America. Think the boat scene in the Notebook, when Noah and Allie get caught in the rain.
Belhaven Neighbourhood
The neighbourhood of Belhaven is a really lovely area of the city to have a walk around and admire the beautiful houses that adorn the streets. It’s incredible to see the southern architecture and how each house is so unique to the next. Whilst you are in the area, stop by Fertile Ground Beer for a drink. This is a great brewery, with outdoor seating and delicious beer, the perfect place to enjoy a refreshing drink in the sunshine.
Where to stay in Jackson, Mississippi
Jackson offers a plethora of accommodations to choose from for all budgets. However, if you really want to treat yourself and play into the whole Southern theme. Then you must look no further than the Fairview Inn. This gorgeous historical property offers an elegant and unforgettable stay, absolutely draped in southern charm.
The boutique hotel is without a doubt the most stunning in town, with only 18 rooms on site it is a truly intimate and special experience to stay here the night. Relax on the porch during a balmy evening, drink in hand, whilst you listen to the chirping of distant grasshoppers. This is what dreams are made of! Our stay at the Fairview Inn was truly a highlight of our time in Mississippi, an experience we will never forget.
Not to mention the hotel has a whole kitchen dedicated to complimentary drinks and snacks for all guests. Yep, you read that correctly!
Where to eat in Jackson, Mississippi
Jackson is blessed with many great restaurants and culinary experiences to get your taste buds tingling, but there are two venues that really stood out to us on our visit to the city.
Elvie’s – An adorable all-day French inspired cafe, serving seasonal foods that showcase Southern farmers. All of their ingredients are sourced locally and within state. You can pop by any time of day to grab something delicious to eat of their wonderfully crafted menu. Although, we’d highly recommend that you make this your breakfast stop.
Pulito Osteria – A beautiful Italian restaurant in the heart of Belhaven neighbourhood, they serve handmade pasta dishes and perfect wood fired pizzas. Highlighting classic Italian flavours that we all know and love. This is a lovely spot to enjoy a romantic evening meal, over a good glass of wine.
Day 3-4: The ‘Little Easy’ Natchez, Mississippi
The best way to describe Natchez is as a quintessential country town, the type that features in a Hallmark movie and makes you think “do places like that really exist”? Well, we can confirm that they do, and Natchez is just as cute, if not cuter than you could imagine, in real life.
Natchez is a world away from the Delta and Jackson. Sitting on the banks of the Mississippi River, you can feel the shift in pace and especially vibe, as you enter the fringes of town. It feels like a close nit community, a good place to live and somewhere you simply cannot skip on a road trip through Mississippi.
Whilst an overnight stay in Natchez definitely isn’t enough time to soak in the beauty that you’ll find here, these are some of the places around town you should check out…
Natchez Trace Parkway
As you travel South from Jackson, you absolutely must take the Natchez Trace Parkway. The Natchez Trace is one of the oldest transportation and trade routes in North America, dating back 10,000 years. Today, it is a scenic byway that cuts through lush forests with plenty of hiking opportunities and historical spots along the way.
The Natchez Trace is what originally inspired us to take this trip to Mississippi and it did not disappoint. The feeling of cruising down this scenic byway, with the tunes up loud and surrounded by nature was just perfect. As you drive along the Trace take your time to stop at the different points of interest. Learning about the significance of this route, as well as admiring the natural beauty that surrounds you.
Natchez Bluff Walk
The best way to take in the beauty of Natchez is to take a walk along the Bluff, this is a trail that follows the length of town, alongside the Mississippi River. From this trail you will get outstanding views across the river and the surrounding landscape. You’ll even be able to see across to Louisiana.
There are benches along the Bluff, we recommend that you take a moment on your walk to just sit and soak in the feeling of this place, it truly is one of the most beautiful towns we have ever visited. If you continue your walk down towards the water’s edge, this area is called ‘Under the Hill’ and is a great spot to catch a sunset over the Mississippi River and Natchez-Vidalia Bridge. If you are lucky, you may even see some steamboats launching or passing by on their way down the river.
Downtown Natchez
Take your time to discover downtown Natchez, wander the quaint streets and pop into the boutique shops that line them. If you are a keen photographer like us, then we recommend that you head to Main Street. We think that this is one of the most picturesque spots in Natchez and makes for some great photos, in the shadow of St Mary’s Basilica.
Longwood House
Natchez is known for its ornate mansions that line the streets, these historic properties offer a glimpse into the southern way of life. Longwood is the crown jewel of historical properties in Natchez and is a must visit for anyone who comes to visit the town.
The house is super unique as it takes on an octagonal shape, with a domed roof feature that almost resembles the kind of architecture you’d expect to find in middle eastern countries. You can tour the house seven days a week between 9am and 4pm. However, the most beautiful part of Longwood, is without a doubt the extensive gardens that are filled with gum trees, with Spanish Moss draping from their branches.
Stepping into the gardens at Longwood is like stepping into a Nicholas Sparks movie. This is another great spot to get some photos and enjoy the peacefulness of nature around you.
Where to stay in Natchez, Mississippi
We stayed in a cosy little rental unit called Bills Place, which we would definitely recommend. The unit is located opposite the Bluff Walking Trail. Meaning when you stay here, you have views over the Mississippi River right on your doorstep.
Bills Place captures the essence of a cosy, local stay in the Deep South. The building itself screams southern charm, with a lovely porch out the front to people watch from. Inside there are two units, each with a bedroom (extremely comfortable bed), kitchen, living room and bathroom. Offering all the facilities that you’d need for a comfortable and memorable stay in Natchez.
What’s more, if you stay over a weekend, you will wake up to the Saturday morning Farmers Market right outside your front door. What better way to start your weekend than mooching around the stalls in the sunshine.
Where to eat and drink in Natchez, Mississippi
Natchez has a rich culture that has been influenced by diverse communities, this has been reflected in the town’s vibrant food scene. Whether you’re looking for classic Southern comfort food, fresh seafood, or international cuisine, Natchez has what you are looking for.
Little Easy Cafe – Whilst down the road New Orleans is well known as the ‘Big Easy’, here in Natchez the town takes on the name as the ‘Little Easy’ due to its likeness with New Orleans, just on a smaller scale. Little Easy Cafe serves hometown food with ease and boozy brunches in a welcoming atmosphere. This is the place to pop into for breakfast or brunch as enjoy a slow morning.
Camp Restaurant – This place has the best views over the Mississippi River, it’s located ‘Under the Hill’ and right on the water’s edge, perfect for catching a sunset with a drink or two. Camp Restaurant is a sports bar offering the largest selection of draft beers in town, but also handmade Southern comfort food, that tastes delicious.
Natchez Brewing Company – If you are in need of an afternoon or evening drinking spot, then Natchez Brewing Company is the place to be in town. This country brewery offers a taste of locally brewed beers, and the onsite kitchen serves up brick oven pizzas, sandwiches and more.
Day 4-5: Mississippi’s Best Kept Secret, The Gulf Coast
Before planning our trip to Mississippi, we admittedly had no idea that the state has a coastline. But it’s true, Mississippi has 62 miles of beautiful coastline, to rival its neighbouring states. The Gulf Coast may well be Mississippi’s best kept secret, from charming coastal communities and white sand beaches to the barrier islands and ocean experiences.
Coastal Mississippi absolutely deserves a place on your Mississippi road trip itinerary. Whilst you are down here, make sure to check out…
Bay St Louis
This little coastal town has been named one of the “Coolest Small Towns in America” and we couldn’t agree more! With friendly locals, historical buildings, beautiful beaches and trendy restaurants. Bay St Louis embraces the heritage and vibe of the Coastal Mississippi region.
We spent a couple of hours here just wandering around the streets and admiring the stunning scenery across the bay. There are plenty of restaurants that line the shore, where you can stop by for lunch or maybe just a drink on one of the many balconies that overlook the ocean.
Gulfport
The drive alone from Bay St Louis to Gulfport is an attraction in itself. As you follow Highway 90 East towards Gulfport, you will have the ocean to your right the entire way. The drive is simply incredible, passing by whitewashed beaches, stunning houses and a never-ending horizon. Take your time as you drive towards Gulfport to stop at a beach along the way and just enjoy how quiet they are too.
Gulfport is where we decided to base ourselves on the Gulf Coast as it is one of the largest settlements, with the most to do. We definitely recommend that you take a walk along East Beach Boulevard, from here you will be right next to Gulfport Beach, which is the perfect place to catch the sunset as you bury your toes into the sand.
Ship Island Excursions
During your stay in Gulfport, you have to take a trip out on the water with Ship Island Excursions. They offer Dolphin watching cruises out on the bay and this is the perfect way to end your Mississippi trip, it was certainly a huge highlight for us. As you head out onto the water, grab yourself a sweet tea from the bar and then settle into the next couple of hours of watching Dolphins play around the boat.
The Dolphins that live in the bay are Atlantic Bottle Nosed Dolphins and they are super playful! We watched them do flips, surf in the waves and swim underneath the boat. The experience was nothing short of magical and the best way to get up close with these amazing creatures.
Cruises run from March through to November and tickets are 28USD for adults and 19USD for children. It is strongly advised that you book tickets online in advance, which you can do here.
Ship Island Excursions also offer a ferry service out to Ship Island, which is a barrier island off the coast of Gukfport. The island is home to a historic fort and has some beautiful beaches to enjoy on a day trip.
Where to stay in Coastal Mississippi
There is something for everyone in each of the beautiful coastal towns. However, as we mentioned before we decided to base ourselves in Gulfport. If you choose to do the same then we recommend that you check into the Almanett Hotel & Bistro. The hotel is situated just a stones throw away from Gulfport Beach, in fact our balcony view looked onto it. The rooms are clean and fresh, sticking with the coastal theme of their environment.
Where to eat in Coastal Mississippi
Coastal Mississippi’s temperate climate and fertile ground makes for exceptional local produce, that just tastes good! Whether you are looking for a casual place to grab a bite to eat or a fine dining experience, you will be able to find it down on the Gulf Coast. This is the place to take advantage of all year-round seafood, and taste some of the Gulf’s freshest catches.
Chimneys Restaurant, Gulfport – Nestled between lush greenery and Gulfport’s waterfront, Chimneys Restaurant has been serving classic coastal cuisine and fresh seafood dishes since 2000. This charming restaurant is perfect for any time of day, pull up a chair on the porch as you listen to the waves lap at the shore. We aren’t seafood eaters ourselves, but they have an extensive menu serving Gulf to table. We can also recommend the Filet Steak, which was the best steak we have ever eaten, it’s well worth a visit.
Patio 44, Gulfport – This modern restaurant in the heart of Gulfport is the perfect place to grab a classic brunch on your way out of the city. Patio 44 serves up all American classics such as waffles, biscuits, grits and fried chicken in a relaxed yet sleek setting.
Final thoughts on a Mississippi road trip
We took a chance on Mississippi not really knowing what to expect. However, we came away from this part of the world, only with a yearning to come back and dig a little deeper. Mississippi offers its visitors everything you could desire from a great road trip: nature trails, historical sites, beaches, good food and that Southern hospitality, you will feel wherever you decide to visit.
5 days simply isn’t enough to really get to know Mississippi, but we hope this guide has offered you some inspiration on where to start your Deep South adventures. If you want to learn about more adventures like this and for more travel tips, you can always join us on Instagram.
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