Winona, Mississippi got its start when Colonel O.J. Moore arrived from Virginia in 1848 and established a plantation in the area. When the Mississippi Central Railroad came through in 1860, they bought a part of Moore’s land and ran tracks which would eventually become part of the Illinois Central Line from Chicago to New Orleans. Moore sold some more land around the station and a few businesses sprung up to serve the rail travelers. When the town was incorporated in 1861, they chose the name Winona, which is apparently the name an Indian Chief would give his first-born daughter. After the Civil War, Montgomery County was organized, and Winona was chosen as the county seat. While the trains no longer pass through Winona, it still sits at the crossroads of highways 51 and 82 and is just a short distance from Interstate 55.It also rests right between the Delta and the Hills regions of the state. Winona has often been called the “Crossroads of North Mississippi”, but I’ve also seen it called the “Art and Soul of Mississippi”, a nickname which I think I prefer. This Norman Rockwellesque town of about 5000 is definitely full of charm and worth a detour from the highway. I wasn’t there long, but I definitely enjoyed my stay in tiny Winona, Mississippi. I hope you enjoy these photos from my visit.
Hi Guys, it’s that time of the week again. It’s been another great week on the road in Mississippi, and I’m happy to share some of the highlights with you here. My week started in Cascilla in the rural center of the state, led me on a quick loop through the Delta with night stops in Cleveland, Clarksdale and Greenwood and is ending right here in beautiful but rainy Vicksburg. It’s been a week of beautiful towns, incredible food, good music and some really great photo opportunities. Despite the gloomy weather which has been a pretty constant companion this week, my spirits are high and I’m enjoying myself out here. I’m finding some good balance and trying to stress less and enjoy more. In all, it’s been a pretty awesome week out here.
Storms came hard in Central Mississippi as my week began, with hail, tornadoes and damaging wind. I was grateful to my friend John and his family for giving me shelter from the storm last Wednesday night (and for two nights before that). By the time I left Thursday morning, the worst of the storms had passed although the clouds persisted. Shadow Catcher was a whole different vehicle with new shocks, and we no longer bounce down the road like Tigger. That would come in really handy on the less-than-ideal roads of the Delta. I went with stiffer shocks because it’s a big van, so it’s not a smooth ride, but it’s enormously improved on what it was last week.
Decending from John’s place in the hills and heading west on Route 8, I came out into the beautiful, pancake-flat Mississippi Delta. Cotton fields hemmed in the road, and the familiar sights of rusted out cars in front of old sharecroppers’ cabins made me feel like I was once again on familiar ground…
Hello Everyone,
It’s great to see you, and I’d like to extend a very warm welcome to our new subscribers this week, I’m happy that you’re here. It’s been a pretty quiet week here in Mississippi, but a busy one as well. I haven’t done a lot of traveling, but I’ve been to some pretty cool places and met some wonderful people. This week has brought me from Columbus back through to middle of the state with stops in French Camp, Kosciusko and Winona. I spent a couple of nights Cascilla in a pretty rural part of the state with my friend John and his family, and then wound up the week traveling northwest into the Mississippi Delta. Of all the time I’ve spent in Mississippi in the past, most of it has been in the Delta, so it’s pretty comfortable to me. I love it here, and have always been fascinated by the music and the culture. Sadly, I know that poverty levels in the Delta are high, and that this factor contributes to both the music and culture of the region, but I’ve also seen the region develop a reasonable tourism industry in the 15 years or so I’ve been coming here, and hope conditions continue to improve for the area’s residents. Regardless of any of that though, it’s always great to be back in the Delta.
When we last we spoke, I had just pulled into Columbus, in the far east of the state near the Alabama border. My first impressions of the town were good, but my lasting impressions were even better. I really found it to be a delightful and hospitable town full of history with surprises around every corner.
Holly Springs was founded in 1836 on land previously occupied by the Chickasaw people after the Treaty of Pototoc Crreek forced them west. New settlers came to the region quickly and scrambled to buy up land and start planting cotton. As the county seat, Holly Springs grew rapidly as well and even more-so when the Mississippi Central Railroad came through in 1855. During the Civil War, the strategic nature of the railroad came into play and Holly Springs was occupied by Ulysses S. Grant and his Army of the Tennessee. Confederate Cavalry Commander Earl Van Dorn rode into Holly Springs before dawn on December 20th, 1862. The surprise attack temporarily cut off the Union supply route as Van Dorn’s men took all the supplies they could carry and burned the rest. After the war, Holly Springs would resume its role as a cotton center and railroad hub. Rust College was established in Holly Springs in 1866 to help educated newly freed slaves in the area. The college is still in operation today, making it one of the oldest Historically Black Colleges and Universities in the South.
Holly Springs today is a pleasant town of about 7500. I was thrilled to see construction going on while I was there and to find a Mississippi town which is growing and improving instead of deteriorating. There are a number of wonderful Antebellum homes to see in town, and the bustling town square has several restaurants and coffee shops when you get hungry. When I was there, I stopped in to the Visitors Center and spoke with Jamie who was super helpful in pointing out all the wonderful things Holly Springs has to offer. It should definitely be your first stop when you go to visit. I had a great day in Holly Springs and loved taking the photos you’ll see in this post. It’s a town on the rise, and I look forward to seeing how far it’s gotten the next time I’m in town.
Hi Everyone, I hope this week’s This Week finds you all well. It’s almost February and I see spring at the end of the tunnel. It’s been a good week out here on the road, my first full week in Mississippi, with plenty of things to keep me occupied. I’ve visited some cool small towns, learned somefascinating history, eaten at some wonderful restaurants and caught up with friends old and new. It’s been good to be back on the road. Before I get started recapping my week for you, I want to give a big Thank You Shout Out to Todd, one of my subscribers, who sent me a huge list of recommendations for my time in Mississippi. Many thanks, Todd, your recommendations will come in really handy in the weeks ahead.
After leaving y’all last week, I did make my way out to the tiny town of Jacinto. The town was founded in 1836 and named for the Battle of San Jacinto in the Texas Revolution. It became the county seat of Tishomingo County and a stately two-story courthouse was built. In 1869, Tishomingo County was divided into three counties, Tishomingo, Alcorn and Prentiss, and the county seat of the new, smaller Tishomingo County was moved to Iuka. The town declined to the point where the courthouse was sold for scrap. Thankfully some concerned citizens stepped in to save the courthouse and the town. Nothing is open there in the winter, but it was still neat to wander around the courthouse and some of the buildings. It was really quiet and pleasant and there are a few houses and cars around so it’s not quite a ghost town, but it’s close. I did get a bit of a scare when I stood on my tip-toes to get a glance through the window and saw a life-like mannequin inside the courthouse. My heart jumped out of my chest.
From Jacinto, I headed down to Brices Crossroads Battlefield and wanted to visit the small Mississippi’s Final Stands Interpretive Center but unfortunately they had recently sustained some tornado damage…
Hey Y’all,
It is great to be back on the road and it is great to be back writing This Week on the Road. I’ve missed you all, and this weekly post and this journey. While it was definitely good for me mentally to go back to work for a few months and then spend some quality time with my friends and family back at home, I feel really good and very blessed and happy to be back on the road.
I left home in Washington DC last Thursday and aimed for my dad’s place in Charleston, West Virginia. It was a cold and windy ride through the mountains, and snow whirled and blew as Shadow Catcher and I made our way west. The winter blast made me happy we were heading south and it felt good to have months ahead of us and only our plans and our wits to guide us. It was wonderful passing through and past some of the earliest destinations of this journey when we first set out way back in November of 2017. It was cold then too and the days were short, and my dad’s place was definitely a point of refuge as I got all of this off the ground. But driving past exits for Blackwater Falls and Weston and Morgantown and Harpers Ferry all brought a huge smile to my face. We’ve come a long way since then and it was good to take a drive down memory lane.
I spent 2 days with my Dad and Judy, and it was great to catch up with them and enjoy their company. I helped them with a few things around the house and they took me out to a nice meal. It’s always great to see them, and it was my last taste of home for a while.
We set off from Charleston on Saturday, headed west into Kentucky and then south from Lexington into Tennessee. This ride took us past even more wonderful memories from this journey…
