A Day in Mississippi…and My First Solo Road Trip

Do you want strange looks when you tell people you are going away for the weekend? Plan a trip to Mississippi and Alabama. You will get a lot of them.

As of last week, I had four states left in my quest for 50 states. There were two left that could be done in one trip – Mississippi and Alabama. To be honest, I probably crossed into both of these states during one of my past travels in the Southeast but I could not be sure so I booked a trip and away I went.

I booked a trip into Jackson and out of Birmingham and rented a car so I could drive between the two. This is a big deal for me because I hate driving so a solo road trip to a place I have never been is a big step for me. I wasn’t sure what to expect. The good thing is that it was summer so at least I didn’t have to worry about snow or ice, which are absolute no-gos for me.  I joke that if it wasn’t for my sister, I would be living in Kansas City because the weather was so awful with snow and ice when I moved to Dallas, I would not have finished that drive on my own. It’s really amazing she didn’t slip an ambien in my water when I wasn’t looking along the way. I would have deserved it because was a mess.

I landed in Jackson and stopped by the rental car counter to get my car. I asked the guy working at the counter what I should do in Jackson while I was there and his response was “Go to Birmingham.” Hmm. We were not off to a great start.

After leaving the airport, my first stop in Jackson was Brent’s Drugs. Brent’s Drugs opened in October 1946 as a pharmacy and soda fountain. The pharmacy was sold off in 2009 but the soda fountain and bar stools remain. Brent’s Drugs piqued my interest because a scene from the movie “The Help” was filmed there. I channeled my best Emma Stone aka “Skeeter” and sat at the counter and enjoyed a milkshake and breakfast sandwich while I was there. (the scene filmed there is where Skeeter meets up with Hilly and her friends sitting at the restaurant table).


I am usually very particular about planning when I travel, especially when I travel solo. The odd thing about this trip for me was that I never really had an agenda in mind. I originally planned to spend a night in Jackson and then a night in Birmingham but I cancelled the Jackson hotel room last minute and decided to stay wherever I ended up on Friday. While I was at Brent’s Drugs, I asked the folks working the counter what I should do in Jackson and where I should go from there. Their response was “drink a lot.”  Hmm. Another sub-par answer. What is it with people who live in Jackson not having a good answer to that question? I kept pressing and FINALLY they started giving me real ideas. The one I liked best was suggesting I check out the Natchez Trace so after I finished eating and paid my bill, I set out to find the Natchez Trace.

Before doing that, however, I stopped by the Mississippi State capitol building to take a look around. Oddly enough, I have been to several state capitol buildings around the US but have never seen the Iowa or Illinois state capitols. I thought the capitol building in Jackson was very pretty. It was also very peaceful around that area so it was nice to just wander around and take photos.

Mississippi+State+CapitolMississippi+State+Capitol (1)

Next up was the Natchez Trace. The Natchez Trace is a long and historic roadway that stretches about 400 miles between Nashville, Tennessee, and Natchez, Mississippi. The route served as a pathway for early Indian tribes in the area and was later used by pioneer settlers, traders and Colonial troops. Now maintained by the National Park Service, the Trace cuts through some of the most dense and beautifully preserved woodlands in the state. It was a beautiful, peaceful drive with lots of historical points to stop at. There were tall trees on both sides of the road and pretty arched overpasses periodically along the way. I drove the highway from Jackson to Natchez. It was the perfect drive for open windows and loud music. Since it was 90 degrees and really humid, I settled for one of the two.

Natchez+TraceNatchez+Trace+MississippiNatchez+Trace (1)Welcome+to+Mississippi

After getting to Natchez, I decided to heed my dad’s recommendation and head to a restaurant in southern Mississippi that my mom and he had been to with friends that he really liked. It is called Don’s Seafood Restaurant and it is located in Picayune, Mississippi. I was told to go there and have the fried oyster po boy. Here is the thing – my dad does not eat seafood. That fact that he liked this seafood sandwich so much told me I had to go check it out.

So away I went. I should have paid more attention to the roads I would be taking to get there. The beautiful drive of the Natchez Trace turned into curvy side roads through Mississippi and Louisiana. The trip to Louisiana was an unexpected surprise. I didn’t have any time commitments so it was fine but not anticipated. I guess the surprises are a fun part of traveling, right?

After a couple of hours driving, I finally made it to Don’s. The parking lot was full so I parked across the street at the grocery store. When I got into Don’s, I asked the woman at the counter if my car would be okay there. After looking at me like I had two heads, she said “yes.” I guess you can take the girl out of the city but you cannot take the city out of the girl. My car would have been towed before I sat down to eat if I tried that in Chicago.


So how was it? It was good. Is it something I would eat a lot? No. Lots of fried seafood isn’t really my thing but it was worth the trip. If you are in the Picayune area, you should check it out.

After dinner, it was time to head to the Mississippi coastline. Gulfport to be exact. I love the ocean/sea and knew that seeing the gulf would be the prefect ending to a long day of driving. I stayed at the Courtyard by Marriott, which was directly across the road from the beach. The hotel was okay but it had a great outdoor pool! Almost resort quality to be honest. It was big with lots of chairs to sit in along the side.

I checked into the hotel and then set out to find explore the beach. The sand was really fine and it was actually a nice beach – not Hawaii but still nice. Ha! I found a seat and stayed through sunset and into the darkness, listening to the waves. It was indeed a great ending to an adventurous day!

Gulfport+MississipiGulfport+MississippiGulfport+Mississippi (1)Gulfport+Mississippi (2)


Leave a Reply