9 Most Charming Town Squares In Mississippi

In Mississippi, the town square often serves as the heart of community life—neighbors cross paths, businesses stay busy, and the architecture shows the town's history. These squares were built around a courthouse or central green, naturally becoming the backdrop for parades, festivals, and everyday errands. Stroll through one today and you might wander past a bookstore where authors still sign their work, step into a bakery that smells like childhood Saturdays, or sit under courthouse steps that have witnessed generations of community milestones. From the Delta to the Gulf Coast, these squares aren’t just places to pass through—they’re destinations to linger in, explore, and experience. Here are nine Mississippi town squares where history, local pride, and everyday life unite in unforgettable ways.

Oxford

Oxford’s Courthouse Square Historic District has long been a gathering place, but it carries a pulse you feel when you arrive. A natural first stop is Square Books, Mississippi’s literary treasure, where you’ll find signed editions, lively author readings, and a cozy upstairs balcony perfect for people-watching. Around the corner, City Grocery serves refined Southern cuisine owned by James Beard-nominated chef John Currence, with an upstairs dining room for special evenings and a laid-back downstairs bar for casual nights out. For a more casual experience, Ajax Diner is also a favorite local hangout.

By day, it’s easy to linger over coffee, browse local shops, and stroll the historic streets. Come fall, though, the square transforms into a festive hub as Ole Miss alumni and students pour in to rally around the football team. The atmosphere turns electric, with live music spilling into the night and conversations carrying long past sunset—a celebration that feels as spirited as it is unforgettable.

Canton

For generations, the town square has served as the town's meeting place—whether to browse the famous flea markets or to enjoy holiday lights that transform the courthouse lawn into something magical. Twice a year, the Canton Flea Market Arts and Crafts Show turns the square into one of the South’s biggest open-air markets, with vendors stretching for blocks, selling everything from hand-thrown pottery to local foods.

On quieter days, the square is just as inviting. The Canton Movie Museum in the courthouse tells the story of films shot here, including A Time to Kill and My Dog Skip. Around the square, you’ll also find cozy dining spots, such as the Daily Scoop, offering ice cream. During December, the Canton Christmas Festival blankets the square in lights, carriage rides, and carousel music, drawing families from across the state to experience the spectacle.

What makes Canton’s Square special is its ability to shift with the seasons. One week, you might browse antiques and crafts under autumn skies; another, you’re sipping cocoa while admiring the glow of holiday lights. The courthouse towers above through it all—steady, timeless, and at the center of it all.

Hernando

Anchored by the handsome DeSoto County Courthouse, the square stretches out with tree-shaded streets and storefronts that welcome you in. On Saturday mornings from spring through fall, the Hernando Farmers Market transforms the square into a bustling open-air gathering, with tables piled high with fresh produce, homemade jams, and baked goods. The air fills with live music and conversation, making it as much a social event as a shopping trip.

The DeSoto County Museum, located just steps from the square, offers an engaging look at local history, featuring Civil War artifacts and blues heritage. For shoppers, The Square Cupboard houses vintage items worth purusing, and when it’s time to eat, spots like AC’s Steakhouse keep visitors and locals well-fed with hearty, down-home meals. Seasonal events also bring the square to life—from holiday parades to open-air concerts that spill into warm summer nights.

What’s most striking is how Hernando’s Square pulls the community together in one place. Whether you’re strolling on a quiet weekday morning, browsing the market on Saturday, or enjoying a festival, Hernando’s Square offers the perfect glimpse into Mississippi’s knack for making its public spaces feel like home.

Holly Springs

Holly Springs has a town square that may be intimate, but it's worth spending time in. Brick buildings and historic storefronts surround the Square, lending a sense of permanence that perfectly complements small-town Americana.

Locally owned businesses give the square its everyday energy. The Retro Rooster, a boutique filled with stylish finds, and Southern Eatery, known for its hearty lunch buffet, keep folks coming downtown. Antique stores round out the mix, their shelves stacked with Southern heirlooms and one-of-a-kind pieces.

For those who appreciate nature, the Strawberry Plains Audubon Center features several miles of peaceful trails and memorable experiences with hummingbirds. Seasonal festivals and parades also keep the courthouse lawn busy, turning Holly Springs’ square into a gathering ground for stories old and new.

Grenada

Grenada’s town square rests at the very center of the community, and in recent years it has enjoyed a fresh revival thanks to the efforts of local residents. Unlike many Mississippi squares, this one follows an open concept—no courthouse stands in the middle. Instead, the lawn is anchored by a graceful gazebo and framed with manicured flower beds, giving it the feel of a welcoming park. Throughout the year, the square transforms into a stage for community life, with events ranging from patriotic parades in the summer to Christmas festivities in December and smaller gatherings that bring neighbors together.

Around the square, you’ll find businesses that give downtown Grenada its heartbeat. First & Green Event Venue, set in a restored historic building just off the square, hosts everything from weddings to concerts, adding new life to the old town center. For unique Cajun and Creole flavors, Orleans Bistro offers a memorable dining spot.

The square also ties into Grenada’s broader identity. Just a few minutes away sits Grenada Lake, one of the largest reservoirs in Mississippi, which brings outdoor lovers into town to explore the shops and eateries before or after a day on the water.

Port Gibson

Port Gibson’s town square carries a quiet grace that feels timeless. At its center, the Claiborne County Courthouse gleams in white, its tall columns and classical design making it one of the most striking courthouses in Mississippi. The surrounding streets hold a mix of historic storefronts, giving the square both character and calm.

Not far from the courthouse, the town’s flavor shines through at Royalty Lounge and Bistro, where Creole-inspired dishes bring a taste of New Orleans flair to this historic river town. Beyond the square, the hauntingly beautiful Windsor Ruins rise from the landscape as Mississippi’s most famous antebellum remnants, their towering columns a reminder of grandeur lost to fire. For another glimpse into the past, Grand Gulf Military Park preserves Civil War earthworks, a historic chapel, and sweeping river views, tying Port Gibson to the broader story of the Mississippi River Valley.

Festivals and parades regularly spill onto the courthouse lawn, filling the square with music, food, and laughter. The town’s deep ties to the Blues give even casual gatherings a rhythm that is true to its Mississippi roots.

Corinth

In Corinth, the town square still hosts seasonal events, and the surrounding streets remind us of Corinth’s Civil War legacy and modern energy. One of the must-visit spots just off the square is Borroum’s Drug Store, the oldest operating drugstore in Mississippi. Step inside for a milkshake, a plate of tamales, or even a slugburger from their working soda fountain. For a heartier meal, Abe’s Grill is just outside of town, offering down-home cooking in a tiny roadside diner that’s become legendary across the region.

History buffs will appreciate how Corinth ties its square into the larger story of the Civil War. Markers and walking tours highlight the town’s importance as a rail crossroads, while the Corinth Civil War Interpretive Center, just a short walk away, deepens the story with immersive exhibits.

New Albany

New Albany’s town square gives this northeast Mississippi town a welcoming center that feels both historic and alive. Strolling here feels easy—slip into shops, find a café, or take a hike all within a few steps.

Start your visit with a stop at Tallahachie Gourmet, which is open for lunch, serving homestyle cooking with recipes that feel like they came straight from a grandmother’s table. The square also hosts community festivals that bring energy to downtown. Each summer, the Tallulah Riverfest fills the square with vendors, live music, and food, while holiday parades and light displays make the courthouse lawn a gathering place for the whole town. With the scenic Tanglefoot Trail just a block away—Mississippi’s longest Rails-to-Trails pathway—it’s easy to combine an afternoon of biking or walking with time spent enjoying the square.

Hattiesburg

Hattiesburg may not have a traditional courthouse square, but Town Square Park has stepped into that role as the city’s downtown gathering place. Built on the site of the old train depot, the park offers wide green lawns, shady walking paths, and a stage that naturally draws people together. Year-round, it hosts various events, including free concerts, outdoor movies, and food festivals, transforming the heart of downtown into a vibrant community hub under the open sky.

Just beyond the park, you’ll see signs of downtown’s revival in the local businesses that line the streets. The Lucky Rabbit, a sprawling vintage store, feels part antique market and part curiosity museum, and it’s become a destination in its own right. For a pick-me-up, Depot Coffee House provides a warm, relaxed spot to grab a latte before exploring more of downtown. A few blocks away, the historic Saenger Theater adds a cultural touch with concerts, stage productions, and film showings that nod to Hattiesburg’s rich artistic past.

There’s plenty to discover here, but visitors shouldn’t skip the downtown district. Between Town Square Park, one-of-a-kind shops, and cultural landmarks, you can easily spend a whole day exploring—and still want to return for more.

From Oxford’s literary buzz to Canton’s flea markets and Port Gibson’s gleaming white courthouse, Mississippi’s town squares each tell a different story. Yet, all serve the same purpose—they bring people together. Some squares carry the weight of centuries, with courthouses that have stood since the 1800s, while others, like Hattiesburg’s Town Square Park, show how communities reinvent old spaces for new traditions.

What ties them all together is how they invite you to slow down. You can sip coffee on a shaded sidewalk, browse a boutique tucked into a century-old storefront, or listen to music drift across a courthouse lawn. Every square feels like its own chapter in Mississippi’s story, a reminder that the state’s spirit often lives in the places where neighbors still meet face-to-face.

If you’re ready to explore Mississippi beyond the highways and big cities, start with these squares. Wander their streets, linger on their lawns, and let the rhythm of small-town life remind you why these places still matter.