10 Hole-In-The-Wall Dessert Diners In Mississippi That Taste Like Family

Mississippi knows a thing or two about comfort food, and when it comes to desserts, the state’s hidden gems shine brightest. Tucked away in small towns and bustling cities, these humble diners and old-fashioned soda fountains serve up sweets that remind you of Sunday dinners at grandma’s house.

Every slice of pie, scoop of ice cream, and homemade cobbler comes with a side of Southern hospitality that makes you feel right at home. From historic drugstore counters to family-run cafes, these spots have been feeding generations with recipes passed down through the years.

They might not look fancy from the outside, but step inside and you’ll discover why locals keep coming back.

Whether you’re craving banana pudding, mile-high meringue, or a simple sundae made with love, these places deliver sweetness that goes straight to the heart.

1. Brent’s Drugs – Jackson

Walking into Brent’s Drugs feels like stepping back to the 1950s, where the soda fountain still bubbles and the counter stools spin just like they did decades ago.

This Jackson landmark has been serving up ice cream treats and fountain drinks since 1946, making it one of the oldest continuously operating soda fountains in the state. The black and white tile floor and vintage decor transport you to simpler times.

Their malts and milkshakes are legendary, made the old-fashioned way with real ice cream and plenty of love. You can watch the staff blend your shake right in front of you, just like soda jerks did back in the day. The banana splits come piled high with three scoops and all the toppings you could want.

Locals have been bringing their kids here for generations, creating memories over ice cream sundaes and cherry Cokes. The staff remembers regular customers by name and their favorite orders.

Every visit feels like coming home to a place where time moves a little slower and dessert tastes a whole lot sweeter.

2. Weidmann’s – Meridian

Weidmann’s has been a Meridian institution since 1870, making it one of the oldest restaurants in the entire state. The dark wood interior and vintage photographs tell stories of generations who’ve celebrated birthdays, anniversaries, and ordinary Tuesdays within these walls.

Walking through the door feels like visiting a beloved relative’s dining room.

Their famous black bottom pie is the stuff of legend, with a chocolate custard base, rum-flavored cream filling, and whipped cream topping that makes grown adults swoon. The recipe has been guarded carefully for decades, and one bite explains why people drive hours just to taste it.

They also serve towering layer cakes and fruit cobblers that arrive bubbling hot from the oven.

The servers know the menu by heart and can describe every dessert in mouthwatering detail. Many have worked here for years, becoming part of the Weidmann’s family themselves.

When you finish your meal, they’ll smile and ask if you’re ready for “the good part,” because everyone knows the desserts are what dreams are made of.

3. Walnut Hills Restaurant – Vicksburg

Walnut Hills brings back the tradition of communal dining, where strangers become friends over shared platters and lazy Susans loaded with Southern classics.

This Vicksburg treasure has been welcoming guests since 1974, though the building itself dates back much further. The round tables encourage conversation and the passing of dishes, just like Sunday dinner at home.

Dessert here isn’t just one slice of pie, it’s a parade of sweets that keep rotating past your plate until you surrender. Peach cobbler, bread pudding, banana pudding, and chess pie all make appearances on the lazy Susan. The banana pudding features real vanilla wafers softened by creamy custard and topped with meringue that’s perfectly browned.

You’ll find yourself reaching for “just one more bite” of three different desserts while your tablemates do the same. The staff keeps the desserts coming until everyone at the table admits defeat.

This style of dining creates memories and friendships, proving that the best meals are the ones we share together over something sweet.

4. The Chimneys – Gulfport

Nestled in Gulfport, The Chimneys serves up coastal charm with a heaping side of homestyle desserts that’ll make you want to move to Mississippi.

The restaurant’s warm atmosphere welcomes both tourists discovering the Gulf Coast and locals who’ve been coming here for years. Friendly faces greet you at the door, and the smell of fresh-baked goods fills the air.

Their bread pudding is a showstopper, served warm with a buttery sauce that soaks into every crevice of the tender dessert. The key lime pie offers a taste of coastal flavor with its tangy filling and graham cracker crust.

Chocolate lovers gravitate toward the fudge cake, which is moist, rich, and absolutely irresistible.

What makes The Chimneys special is how they balance restaurant quality with home-kitchen heart. Each dessert tastes like something your favorite aunt would make for a special occasion. The portions are generous without being overwhelming, and the presentation is simple but appealing.

After your meal, you’ll understand why people plan their Gulf Coast trips around a stop at this beloved spot.

5. The Tatonut Shop – Ocean Springs

Ocean Springs is known for its artistic vibe, and The Tatonut Shop fits right into this creative coastal community with personality to spare. This little shop proves that donuts aren’t just breakfast food, they’re legitimate dessert that can end any meal on a high note. The playful atmosphere and unique flavors make every visit an adventure.

Forget plain glazed donuts because here you’ll find creative combinations that change with the seasons and the baker’s inspiration. From maple bacon to lemon lavender, each donut is crafted with care and quality ingredients.

The yeast donuts are impossibly light and fluffy, while the cake donuts offer a denser, more satisfying bite. They also serve donut holes perfect for sharing, though you might not want to.

The staff’s enthusiasm is contagious as they describe the day’s offerings and help you choose from the colorful display. Local coffee pairs perfectly with whatever donut calls your name.

Whether you stop by after dinner or make a special dessert run, The Tatonut Shop delivers sweetness with a side of Gulf Coast charm that keeps people coming back.

6. Pop’s Family Diner – Mantee

In the tiny town of Mantee, Pop’s Family Diner serves up the kind of honest, homemade food that makes small-town Mississippi special.

This unassuming spot doesn’t need fancy decorations or trendy desserts because what comes out of their kitchen speaks for itself. The diner hums with conversation and the clatter of forks on plates as neighbors catch up over coffee.

Their desserts rotate based on what’s fresh and what Pop feels like making, which means every visit brings something different. The fruit cobblers showcase whatever’s in season, from blackberry to peach to apple. Their pies feature tall meringues that wobble when the server sets them down.

The chocolate cake is simple but perfect, with fudgy frosting that doesn’t try too hard.

What you’ll remember most isn’t just the taste but the feeling of being welcomed into someone’s home. The staff knows most customers by name and remembers how you like your pie served.

In a world of chain restaurants, Pop’s reminds us why small-town diners matter and why their desserts taste better than anywhere else.

7. Movie Star Restaurant – Hattiesburg

Movie Star Restaurant brings a touch of Hollywood glamour to Hattiesburg while keeping its heart firmly planted in Southern tradition. The walls display vintage movie posters and celebrity photos, but the real stars here are the desserts that have kept locals coming back since the doors first opened.

College students from nearby University of Southern Mississippi mix with longtime residents at the counter and booths.

Their peanut butter pie is famous throughout the Pine Belt region, with a creamy filling that balances sweet and salty perfectly. The chess pie, a Southern classic, arrives with a crackly top and custardy center that melts on your tongue.

Fresh fruit pies change with the seasons, and the strawberry pie in summer is worth planning your day around.

The servers move efficiently through the dining room, somehow remembering orders without writing them down and keeping coffee cups full without being asked. They’ll tell you honestly which pie is freshest and might even sneak you an extra dollop of whipped cream.

This combination of great desserts and genuine hospitality creates the kind of experience that turns first-time visitors into regulars.

8. Sugar’s Place – Jackson

Sugar’s Place dishes out soul food with so much flavor and love that you’ll want to hug the cook after your meal. Located in Jackson, this restaurant specializes in the kind of cooking that feeds both body and spirit.

The atmosphere buzzes with energy as families gather around tables loaded with comfort food that tastes exactly like home should.

Their sweet potato pie is a masterpiece of Southern baking, with a silky filling spiced with cinnamon and nutmeg that makes you understand why this dessert is a cultural treasure. The peach cobbler arrives in a bowl with a golden crust that crackles when you break through to the sweet fruit beneath.

Red velvet cake, moist and topped with cream cheese frosting, disappears from your plate faster than you planned.

The name Sugar fits perfectly because everything here is made with sweetness and care. Portion sizes are generous, meant for sharing or taking home for later.

The staff treats everyone like family, checking to make sure your meal is perfect and encouraging you to save room for something sweet. You’ll leave with a full belly and a happy heart.

9. Borroum’s Drug Store – Corinth

Borroum’s Drug Store has been serving ice cream and sodas since 1865, making it one of the oldest drugstore soda fountains still operating in America. The original wooden fixtures and vintage signs create an atmosphere that feels like a living museum where you can actually eat the exhibits. History seeps from every corner of this Corinth landmark.

Their ice cream sodas are made the traditional way, with syrup, soda water, and hand-scooped ice cream mixed right at the marble counter. The banana splits are architectural wonders, carefully constructed with three scoops and all the classic toppings.

Milkshakes come thick enough to stand a spoon in, blended to creamy perfection. They also serve old-fashioned sundaes with hot fudge that hardens slightly when it hits the cold ice cream.

Sitting at the counter on a swivel stool, you can imagine all the people who’ve sat in that same spot over the past century and a half. The staff maintains the traditions while making everyone feel welcome.

This isn’t just dessert, it’s a taste of American history served one scoop at a time in a place that refuses to forget its roots.

10. Phillips Grocery – Oxford

Phillips Grocery has been an Oxford institution since 1882, operating out of a building that looks like it hasn’t changed much since the early days.

This combination grocery store and diner is famous for its burgers, but locals know to save room for the desserts that have been part of the menu for generations. The cramped quarters and vintage atmosphere add to the charm rather than detract from it.

Their homemade pies rotate daily, with classics like chocolate, coconut, and lemon appearing regularly on the menu. The slices are generous, cut from pies baked fresh in the tiny kitchen behind the counter. Chocolate lovers should try the Mississippi Mud Pie, rich with chocolate and pecans.

The coconut cream pie features real coconut in both the filling and the topping.

University of Mississippi students and professors rub elbows with longtime Oxford residents in the narrow aisles and at the few tables. Everyone’s equal when it comes to getting a slice of pie at Phillips.

The no-frills presentation and authentic atmosphere remind you that the best desserts don’t need fancy plating or trendy ingredients, just good recipes and people who care about what they serve.