Are you looking for the best things to do in Oxford, Mississippi? Read on for a quick synopsis of Oxford, MS’s history, restaurants, and the best Oxford activities. 

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Y’all: Oxford, Mississippi is an absolute gem. We spent an action-packed 3 nights and 4 days wandering the gorgeous downtown square on our epic road trip, and I wish we’d had even more time.

Oxford, Mississippi, is a town of 27,366 people located in the northeastern corner of the state, about 75 miles from Memphis, Tennessee. The University of Mississippi, fondly known as Ole Miss, rests to the west of the historic downtown square.

There’s a lot of history in Oxford, which we’ll scratch the surface of below, but, like many college towns, there’s a strong youthful energy here, and a delightful dose of sophistication. Like many old municipalities in the South, the heart of the historic district is structured around a pretty town square. The grandiose Lafayette County Courthouse, with its ornate clock tower, is visible from North and South Lamar Boulevard, creating quite the impression as you approach the restaurants and businesses.

The History:

Oxford, Mississippi lies on land once owned by the Chickasaw Nation. Originally a trading post, 50 acres of land (now Oxford) was incorporated in 1837 and named for the "English center of learning, reflecting the townspeople's early desire for a university," according to Encyclopaedia Britannica. The townsfolk soon got their wish, and the University of Mississippi was chartered in 1844 and opened in 1848. 

During the American Civil War, Ole Miss served as a hospital, and many Oxford residents perished during the war. In 1862, Oxford was occupied by Union forces under Ulysses S. Grant and William Sherman, and it was burned to the ground in 1864. A few buildings survived, one of which is Neilson's clothing store, and it holds the distinction of being the South's oldest documented store. (It also features a letter from Nobel prize-winning American author William Faulkner, who staunchly refused to pay his tab at the department store.)

William Faulkner, one of the South's most famous authors, lived in Oxford at his estate, Rowan Oak, until 1962. Much of the character of Oxford made it's way into his famous fictional town, Jefferson, and county, Yoknapatawpha. 

In the fall of 1962, Oxford drew national attention during the Ole Miss Riot, when African American James Meredith was barred from enrollment. This dark period in the town's history resulted in violence, and 3,000 nationalized Mississippi National Guard and federal troops camped in the city. 

The town has grown and flourished in the more than 60 years since the Civil Rights movement, and today, Oxford is an adorable hub of food, culture, and style. Lucky Magazine even went so far as to boldly claim Oxford as the "Cultural Mecca of the South," so let's dive in. 

Disclaimer: My husband and I are self-proclaimed hip travelers, but we are in our 30s. If you're looking to tap into the Ole Miss college bar scene, please note that we're into fine wine and craft cocktails and being in bed with a noise app on by 11 o'clock. 

The Vibe:

There’s a lot of energy and style in Oxford, particularly for a town that size. The proximity of Ole Miss brings a younger demographic and a breath of fresh air to the historic square, and the thriving collection of trendy boutiques, hot yoga studios, restaurants, and bars reflect that. You’ll find upscale on-trend boutiques, the coolest set of independently owned bookstores, and creative eateries - be sure to poke your head in some of the alleyways off the main square. There may be a sandwich shop or speakeasy hiding in there!

We also met some of the warmest and most welcoming people on our road trip in Oxford, and we had some great conversations, especially with the staff at Rowan Oak, City Grocery, Bar Muse, and the Oil Shed.

The Charm:

The town square and surrounding streets are flanked by adorable, hip businesses housed in historic buildings. A British-style telephone booth sits in one corner, not far from a detailed statue of William Faulkner. Beyond the square, picturesque Southern homes sprawl out in all directions, often beneath old-growth trees.

14 Places to Hit in Oxford, MS

Square Books

Square Books is basically the best bookstore ever. The independently owned bookstore (actually, it’s four separate stores) strengthens Oxford’s literary tradition by offering carefully curated literary selections in four distinct spaces around the beautiful town square. Square Books offers a lovely selection of books with a cafe and balcony on the second floor (I bought Prince Harry’s tell-all autobiography here). Off Square Books rests on the opposite end of the adjoining block, and there you’ll find a binge-worthy collection of cooking, design, and lifestyle books. Square Books Jr. sells children’s books, and Rare Square Books feature collectible, vintage, first-edition books across a broad price range.

City Grocery

Plan a date night at City Grocery, Chef John Currence’s contemporary American dining spot. The fancy-without-being-fussy establishment is nestled inside a Reconstruction-era former livery stable on the Oxford square. The food is delicious seasonal and local fare, and I’ll be thinking about that Veggie Pot Pie for months to come. 

Rowan Oak

William Faulkner’s Oxford home is absolutely worth the wander, particularly if you’ve ever read any of his works. I read Light in August at a formative time in my life, and that particular work is part of why I went on to get a second major in English. Obviously, this made a trip to the sprawling, Cedar-lined grounds a must for me personally, but the home is also a well-preserved slice of a bygone era. It still features Faulkner’s hand-scrawled notes on his office walls.

The modified Greek Revival home and its 29 acres are open to the public year-round, but you’ll need to bring $5 in cash to tour the home.

Bar Muse

William Faulkner fully endorsed “a little whiskey” as one of the essential tools of his trade, so put a visit to Bar Muse on your Oxford itinerary. Bar Muse is a hip, cozy craft cocktail bar inside the historic Lyric theater, built in the late 1800s. Today, James Beard nominee Joseph Stinchcomb mixes up delightfully balanced and surprising cocktails (and mocktails!) behind the bar. 

The Oil Shed

Fellow plant ladies, this one’s for you! Run, don’t walk to The Oil Shed. The Oil Shed offers a lovely selection of indoor and outdoor plants, planters, beautifully curated gifts, and candles. I stumbled upon this Oxford gem after an enthusiastic antiquing session at The Depot across the street, and it was a highlight of my trip.

Landry’s

This delightful menswear shop offers a great selection of clothing and lifestyle items with fun vintage props interspersed throughout. The staff was very personable as well.

The Sipp on South Lamar

My love of small towns is frequently at odds with my equally fervent love of wine bars, so The Sipp on South Lamar was an oenophile’s oasis on our cross-country road trip. (Literally, I can’t remember the last time I was so excited to see a wine list with more options than “red, white, and Moscato”.) The extensive wine list features more than 50 wines, and the whiskey list features more than 100 options. Slide onto a bar stool for a glass or settle into a booth for dinner at this sleek, contemporary neighborhood hang.

The Depot Antique Mall

If you love hunting for vintage treasures, plan to spend an hour or so at The Depot. With more than 100 booths, you’re sure to find something you love. 

Fresh Ink

This Polly Pocket-sized paperie is located just off the Oxford square. Though this may literally be the smallest store you’ve ever set foot in, it’s full of delightful cards, colorful stationery, and amusing gifts. 

Saint Leo

Whether it’s a special occasion or you just like great food in a swanky hideaway, Saint Leo’s is worth putting your nice shirt on. (When you’re traveling in a van, there is only one nice shirt.) This chic, upscale eatery serves up tasty seasonal, locally-inspired eats; make sure to order the House-Marinated Olives to start. We also loved the Chopped Salad and the decadent Mezzi Rigatoni.

Neilson's Department Store

If you skimmed over the History section above (no judgment, at least this isn’t a recipe blog), you probably missed that Neilson’s Department Store holds the distinction of being the South's oldest documented store. The veteran retail shop survived the burning of Oxford during the Civil War, and today is a top-notch purveyor of luxury clothing.

The Byrd House Cafe

Start your day out on the right foot at the Byrd House Cafe. The stylish eatery serves flavorful organic fare, such as smoothies, salads, freshly pressed juices, toasts, and smoothie bowls. Pro tip: Add an egg over easy to the Buddha Bowl.

Hinton & Hinton Men’s

I have to say, the quality of shopping in Oxford is really superb for a town this size, and Hinton & Hinton is worth a wander, even if just to check out the massive vintage bar that functions as the check-out desk.

Southside Gallery

Conveniently located on the Oxford square, this contemporary art gallery showcases a lovely selection of work that ranges from ceramics to abstract photography.

Plus, 5 Places That Look Cool That We Didn’t Get to 

Wonderbird Spirits Distillery

Ok, this highly-esteemed distillery was at the top of my list when we set foot in Oxford, but it is temporarily closed for renovations. Wonderbird Spirits gin, which received Garden & Gun’s Made in the South Award, uses fermented Mississippi Delta Rice and traditional sake-making methods for a uniquely complex and layered gin. Tours and tastings are offered by appointment only.

Lyric Theater

The epitome of cool, the renovated 1800s theater is steeped in history but boasts an interesting, contemporary line-up of shows and events. Check their calendar to see what’s happening while you’re in town.

The Sleepy Cactus

Housed in a refurbished service station, the Sleepy Cactus is one of the newcomers to Oxford’s dining scene. Venture off Oxford’s main square for their tasty-looking menu of breakfast tacos and spacious outdoor patio.

Ole Miss

Admittedly, I’m not much interested in going out of my way to see schools I didn’t personally attend, but I’ve heard Ole Miss is very pretty. If we’d had another day, I would have checked out the museum. If you have favorite spots on campus, drop them in the comments below.

Ajax Diner

Ajax Diner boasts an adorable retro interior and a solid menu of classic Southern fare. It came highly recommended, but we just ran out of time.

Have you been to Oxford, Mississippi? What are your favorite places to dine, shop, and drink? Leave ‘em in the comments below!