Jackson, Missouri: What to do and Where to go

Going back to the place one grew up can bring back several emotions. For some, it’s despair, hatred, or an inconvenience on the holidays. For others, it’s elation, relief, and joy. As someone who has spent her life dreaming of traveling, it’s a mix. After a childhood of dreaming about leaving, I abandoned my hometown before I even left. I’ve been everywhere in this town, done everything, and moved on from it well before my teenage years. I dreamt of drinking coffee in Paris and riding horses in Jordan. This made Missouri feel obsolete.

After traveling the United States for the last four years, my whole life has shifted and upended multiple times. Traveling has changed my location, identity, and perspective. I came home a different person and I intend to use that to my advantage.

Thus, my micro-adventures. I decided to travel ‘through’ my town. I want to see what the world of Jackson, Missouri has to offer. What can I get up to in a place I thought I knew everything about?

Old Favorites

Ground-a-bout

I spent hours in this coffee shop, both with my friend Rachel and by myself. Every Thursday, we would have coffee before school and talk about life, childhoods, and where we wanted to go. The Ground-a-bout is covered in memories of my high school years, and it held up.

The coffee here is delicious. From frappes to lattes to (sometimes) cold brew, everything here is to die for. It perfectly encapsulates the small-town vibe, with everyone sitting together and greeting each other. You can often see the owner, Bob Schooley, in the corner, chatting with friends. If you need your coffee fix anywhere in Southeast Missouri, this is your place.

A little tip: if you go during the holidays I highly recommend the fireside latte. It’s a different holiday drink from your typical peppermint mocha, but it’s absolutely delicious. Mixed with mocha, toasted marshmallow, and hazelnut, it makes me feel more Christmas-sy than the holidays lights. (I’m lying, but only slightly).

Jackson Donuts

The special treat of my childhood. I can’t believe I survived without them until my high school years. Jackson Donuts was the only donut shop in Jackson and remains the only pure donut shop there today. Why? Because it’s so good we don’t need another. My friends and I would go here to treat ourselves, our friends, and our classes. Donuts from this place made any gathering a celebration.

Trail of Tears

The place every Jackson child goes at least a few times. We spent hours there hiking, picnicking, and even kayaking the lake. There were school trips, family trips, and just-for-fun trips. I did my first “kayak and run” race out there, and it was an absolute blast. I was not prepared for how different trail running was compared to road running. This is where I first fell in love with trails and nature, and I make a trip here almost every time I return.

Stooges

You wouldn’t think it just by looking at the place, but Stooges is one of the best restaurants in town. They host live music, great food, and a rustic atmosphere. My sister would take us here to celebrate or if she was feeling nice.

Rod is the owner and an active member of the community. If you’re looking for someone to be in the know around there, Stooges is your place. Don’t forget your wings and a burger!

Downtown

Our downtown area is… small, to say the least. That’s not to say there aren’t some great stores! There are a few eclectic shops, boutiques, a music store, and a dress store. It also has a Historical museum with ever-rotating displays for you to see.

For a stop that should only take you an hour or two, it’s well worth the look. Don’t forget to pop into tractors for a bite if you’re feeling hungry!

New Adventures

Cheesecake Ninja

I have been gone for a few years, so when I heard a cheesecake place opened up in downtown Jackson, my sweet tooth was already there. Let me tell you, this place did not disappoint. The first thing you smell when you step inside is a sugary sweetness that gets your tastebuds watering. The food does not disappoint. I had a “cleaning out the pantry” cheesecake that included several things (including butterfinger, oreo, and caramel) the employee listed off with astounding speed.

Their name can be deceiving because they have so many more options! The shop worker greeted me with their lunch special, chicken and dumplings. They have a whole menu of meals, desserts, and grab-and-go meals. There is a couple of cute places to sit in and out of the shop, so feel free to have a seat and take in the delicious aroma. And, of course, order a few of the mouthwatering cheesecakes.

Mario’s Italian

Jackson’s first authentic Italian restaurant, this place hosts a large menu to keep your pasta and pizza cravings at bay. They have daily specials to keep you coming back on a budget, and a small seating area to sit and chat! This is the perfect place to pick up some frozen treats for later or an entire plate right now.

Conclusion

Jackson has grown since I left. We added an Aldi’s (a small chain grocery store), a few restaurants, and a second roundabout, but it will always be my hometown. Getting to leave and live across the United States for years on end has allowed me to fully appreciate everything my town has to offer, even if it is mostly food.

There will always be something different about being home. This is a place I can walk downtown and see familiar faces, where I don’t have to pull up my GPS, and I already know all my favorite spots. Out of everywhere I’ve been, Jackson, Missouri, still holds a special place in my heart.

What are your favorite places and activities in your hometown? Let me know in the comments below, maybe I’ll be able to stop by there someday! Thanks for reading, and if you want more bookish and travel content join my newsletter! I send out small-business highlights, travel stories, book reviews, and more every month. Stay brave!