Oxford, Mississippi, blends literary history, college-town energy, and a bustling food scene into one walkable, welcoming city. From gallery-hopping and shopping on the Square to Creole cuisine and live music, here’s how to spend an unforgettable weekend in Oxford.
Day 1: The Square, Ole Miss, and Faulkner
Morning
Kick things off at Big Bad Breakfast, where unapologetically Southern classics set the tone for your weekend. Expect nostalgic touches like checkerboard floors and leather barstools. Order house favorites like the Cathead Chicken Biscuit, smothered in sausage gravy, or the Creole omelet, packed with Andouille and peppers. Arrive early—this spot’s popular on weekends and they don’t take reservations.
Walk over to the University of Mississippi campus to explore its most iconic corners. Wander through The Grove, a ten-acre oak grove famous for SEC tailgating. Make your way to the Lyceum, the school’s oldest building, to admire its grand white columns and bell tower. Pause at historical markers throughout Lyceum Circle to learn about James Meredith’s enrollment and the campus’s role during the Civil Rights Movement.
Head to the Square, known locally as the town’s “living room.” Walk streets lined with late-19th-century storefronts and independently owned shops. Make stops at Square Books and Off Square Books to find your next great read, and don’t miss the rotating art exhibitions inside spotlighting regional artists. Park nearby and stroll the ultra-walkable Square on foot.
Afternoon
Settle in for lunch at Ajax Diner, a beloved Oxford gem known for its Southern comfort food staples, no-frills atmosphere, and fast-paced service. Order the country-fried steak sandwich or fried catfish, and don’t skip the hashbrown casserole or cornbread. Come hungry—portions here are generous. Beat the lunch rush by going early or slightly after peak lunchtime.
Prefer something a bit more elevated? Book a table at the Creole-inspired Bouré, where Louisiana flavors and Mississippi ingredients come together in a rustic-chic setting. Start with gumbo or crawfish egg rolls, then move on to jambalaya or fire-roasted seafood cakes. If it’s nice out, request balcony seating upstairs for show-stopping views of the Square.
Take a self-guided tour of Rowan Oak, the historic home of William Faulkner. Step inside the Greek Revival house where Faulkner wrote many of his most famous works. Visit his writing room, see original furnishings, and spot the penciled manuscript of A Fable written directly on the wall. Outside, roam four acres of landscaped grounds, antebellum gardens, and wooded paths, plus the stable Faulkner built for his horses.
Back at the Square, browse contemporary works at Southside Gallery, known for its curated mix of paintings, ceramics, sculpture, and fine crafts. Continue your self-guided art tour at the Powerhouse Community Arts Center, where you’ll find rotating exhibitions and artist studios inside a restored industrial space. Wrap up your afternoon at Lamar Park—a lakeside park named for Oxford’s first female mayor. Walk the short, flat trails or relax near the water.
Evening
Book a table at City Grocery to dine at one of Oxford’s most popular restaurants. Expect white tablecloths, exposed brick walls, and refined Southern dishes with an inventive twist. Choose a varietal from one of the strongest wine lists in North Mississippi. Try the acclaimed shrimp and grits, duck confit, or green curry catfish stew. Book in advance—weekend tables fill up fast.
For a cozier and more relaxed vibe, grab dinner at Snackbar instead. Located just off the Square, the neighborhood haunt boasts a seafood-focused menu with some of the area’s best oysters. Savor the fried oysters with blackened aioli, or keep it fresh with oysters on the half shell. Pro tip: Sit at the bar to watch the shucking in action. Dig into the Gulf shrimp or the Cajun catfish and chips; both are standouts for a reason.
Catch a live show at Proud Larry’s, a legendary music venue that helped launch bands like R.E.M. Grab a cocktail or a craft beer at the upstairs bar, then head downstairs for an eclectic lineup of indie rock, Southern bands, and touring acts. Shows run every weekend, so check the schedule in advance. Prefer something low-key? Grab dessert at The Oxford Creamery, a “farm to cone” spot serving homemade ice cream for nearly a century. Treat yourself to a scoop of Banana Puddin’ or Butter Pecan, or ask about their seasonal flavors.
Day 2: Scenic Parks and Easy Exploration
Morning
Ease into the day at Square Books Café, tucked away on the third floor of the five-story Square Books. Sip coffee or a caramel latte, nibble on biscotti, and take in the walls covered with framed photos of authors and celebrities who’ve passed through. Grab a seat on the balcony overlooking the Square for a calm, quiet start to your day.
If you missed any shops yesterday, take time now to browse for Mississippi-made goods around the Square. Stop by Ginger G or Style Assembly for stylish women’s clothing, and visit B‑Unlimited or Rebel Yell for a vast selection of Ole Miss apparel and gifts.
End your morning at Avent Park, a neighborhood spot with a more local feel than campus green spaces. Walk the loop trail, relax on the open lawn, or play a game of tennis or disc golf. Visiting with kids? Don’t miss the castle-inspired wooden play structure.
Afternoon
Have lunch at McEwen’s, where white tablecloths and refined Southern dishes turn midday dining into an occasion. Its central location on the Square and warm, friendly service make this spot an Oxford staple. Order the fried catfish po’ boy, grilled pork tenderloin, or the farmer’s plate showcasing whatever local farmers picked that week.
For something more casual, try Volta Taverna—a Greek-inspired joint in a converted gas station. Share a plate of Hotty Toddy Balls (fried garlic mashed potatoes with bacon and mozzarella) before digging into a beef and lamb gyro or Mediterranean farro bowl. Pair your meal with a margarita or frozen mojito from the bar, and enjoy the bright, unfussy atmosphere.
Want to escape campus energy for a bit? Take a scenic drive north on Mississippi Highway 7 toward Sardis Lake. Along the way, cruise past farmland and grazing cattle before reaching wooded shorelines and expansive water views. Cast a line from one of the lake’s fishing areas, go for a short stroll along the shore, or take in the views from the car before returning to town.
Visit the University of Mississippi Museum to see the works of talented artists from Mississippi and around the world. Explore permanent collections ranging from Roman antiquities to Southern folk art, and don’t miss the ancient Greek pottery gallery. Check out rotating exhibitions highlighting history and culture, like Knowledge in Bloom, Diversity in Flight—a collection of relief prints featuring the national flowers of different countries.
Evening
Settle in for dinner at Saint Leo, a modern Italian eatery serving up wood-fired pizzas and fresh pasta. Embrace warm wood finishes, a sleek marble bar, and soft lighting. Order the roasted mushroom pizza, burrata and soppressata pizza, or bolognese pappardelle. Alternatively, grab dinner at SoLa for chef-driven Southern cuisine built around seasonal ingredients. The menu changes often, but expect dishes like braised short rib, Gulf fish piccata, and grilled oysters.
Cap off the weekend with drinks at The Coop, perched atop Graduate Oxford. Soak up collegiate-inspired decor that blends college-town nostalgia with modern design—think leather accents, brass fixtures, and crest motifs. Find a seat on the rooftop deck for panoramic views of the campus. Choose between specialty drinks like the Shimmering Martini and the Coop Old Fashioned, and raise a glass to a memorable weekend in Oxford, Mississippi.
