Square Up: Let’s take a visit to Oxford, Mississippi

Charming, beautiful, and homey describes Oxford: all words that students and natives alike have used to describe Oxford, Mississippi, affectionately and casually known as ‘OX.’ The town is home to the University of Mississippi—or Ole Miss—and thousands of residents who love the town more than they love their crawfish boils. And, whether you’ve lived in north Mississippi all of your life, or the closest you’ve come to Oxford and Ole Miss is watching The Blind Side on TV (shout out to you, Michael Oher!), Oxford offers everything you will ever need in a weekend get away, and so much more.

Featured in both New York Magazine Travel and Vogue Magazine, Oxford has never been shy when it comes to publicity. Actually, Oxford’s picture-perfect downtown Square was a site of shooting for the forthcoming NBC production ‘Bluff City Law,’ and is also the location for the town’s annual Double Decker Arts Festival. With unique English telephone booths and bright red double decker buses, The Square takes a new twist on Southern charm that deserves to be publicized.

When it comes to the campus, Oxford residents take pride in the beauty that Ole Miss offers… I mean, it’s called the Harvard of the South for a reason! From walking down the school’s historic Walk of Champions in The Grove, the school’s one and only football tailgate location, to hiking the trails leading to William Faulkner’s Rowan Oak, Magnolia trees and tulips line the campus. Needless to say, every part of your trip to Oxford will be pleasing to the eye.

So, without further-a-do, here’s your exclusive Pointster itinerary to exploring Oxford, Mississippi for a weekend:


Lets check into our hotel Friday night! With an array of charming hotels, Oxford is no stranger to providing you with the most comfortable stay, no matter where you stay. Here are our top three hotel choices:

The Chancellor’s House — Oxford’s Chancellor’s House is home to 38 rooms, including six suites with private balconies overlooking downtown Oxford. This hotel gives a traditional, yet modern, vibe that is hard to compete with. Whether you want to enjoy a drink on the patio, or a book in the library, The Chancellors House is sure to impress. The Chancellor’s Grill, designer bath amenities, and luxurious Rivolta Carmignani Egyptian cotton linens will be the icing on the cake for a stay at this hotel!

The Graduate Hotel — Graduate Hotels are boutique hotels in college towns spanning all across the country. The Graduate Hotel at Oxford is home to10 different types of room layouts and two amazing restaurants, The Coop (a rooftop bar) and Cabin 82, a porch-side style cafe that embodies Southern charm. The entire hotel features vibrant colors, with pink wood floors in the lobby, and is inspired by the concept of “youthful optimism.”

The Courtyard by Marriott — Oxford’s Courtyard Marriott is located right off of The Square, less than a mile from the Ole Miss campus, and is walking distance from some of Oxford’s best restaurants. The Courtyard gives travelers seven possible room layouts for reservations, access to the hotel’s rooftop bar, the Green Roof Lounge, a private shuttle, and a full gym. This hotel is centrally located and will give cater to any and every need you’ll have while in Oxford.

After traveling all day and checking in, you’re going to want to have a relaxing night before exploring Oxford the next day. That’s why we’re going to spend our Friday night in Oxford with a luxury dinner at the Oxford Grillehouse. Oxford Grillehouse is a Southern style steak and seafood restaurant  located on The Square, yet away from the hustle and bustle of rowdy college students. From fried green tomatoes, to blackened Mississippi catfish, to a dry aged Ribeye, Oxford Grillehouse will give you a great first impression of Oxford’s food and nightlife options!

After dinner, lets get back to the hotel, we have a lot to look forward to tomorrow!


Wake up and get going! Oxford residents are up and at ‘em on Saturday mornings to get to the most popular breakfast restaurant in the entire city, John Currence’s Big Bad Breakfast, and you will be too. But beware, if you get there too late, you’ll definitely wait. Big Bad Breakfast, or BBB as OX residents call it, is located just north of The Square. BBB says “One visit to BBB will guarantee you never look at a breakfast plate the same again…” and boy, is that right! Here’s a pro tip: our favorite meals at BBB are the Big Bad Quesadilla and the cheesy grits… You’ll thank us later.

After BBB, lets take a rest and then let’s explore historic Oxford. That’s right, we’re hiking over to William Faulkner’s Rowan Oak! The historic site was once Faulkner’s home, but now offers tours to visitors, or anybody else interested in Faulkner’s history! Be sure to pick up an original bookmark from the site after exploring.

Just like Oxford is known for Ole Miss, its known for its library! We’re continuing on our path of literature to look at all Oxford has to offer in terms of books and education. At Square Books, located on (you guessed it!) The Square, you will find any book you could ever think of. From Shakespearean poetry, to today’s newest novels, to even journals designed for our Pointsters to record their bucket list, you wont leave empty handed.

Lunch time! Are we hungry again? Who cares! Even if you’re not hungry, you’ll still want to explore all of Oxford’s food options. Since we’re already on The Square, lets go to one of Oxford’s most popular on-square sites: Ajax Diner. Ajax is known for its Southern comfort food and one of the Manning Family’s favorite spots to eat. Plus, you can never go wrong with chicken and dumplings. With low prices and almost limitless options, you’ll come to love Ajax almost as much as the Mannings do.

Post lunch, you may want to walk around The Square, or sit on the rooftop of one of our favorite hotels, but this time is up to you. Until dinner, take the time to explore and get to know the town.

For an upscale, but affordable, dinner, our favorite spot is Oxford’s most popular sushi restaurant, Jinsei. Featuring a long list of award-winning cocktails, including this spring’s seasonal Game of Thrones themed cocktail menu in honor of the forthcoming Season Eight, Jinsei has become known for its creativity and fresh sushi. While Jinsei is not on The Square, it’s located north of it, right by BBB! Though it’s always packed, Jinsei will always be worth the wait! Our favorite appetizers from this restaurants are the Grilled Shishito Peppers, the River Rock, and the Tebasaki Wings! Disclaimer: any sushi roll you try here, you will love (that’s why we couldn’t choose just one to tell you to get).

If you’re feeling up for it after your *mouth watering* dinner, the Oxford Square offers a lot of college bars that anybody can enjoy! For an original experience, try out one of our favorites: Funky’s, a New-Orleans style daiquiri and pizza bar. Funky’s frequently offers oldies night, which is laden with songs that’ll bring you back to your most prominent memories of the 80s and  90s! Or, if you’re feeling more blues-y take a walk up the street to Rooster’s Blues House, a classic Blues bar that’ll always have live music. Whichever you choose to go with, you’ll be in for a treat.


Sleep in and relax, our plans don’t start until around 12 p.m. today, but WOW, they’re going to be great! Even though brunch has developed an upscale reputation, this doesn’t stop Oxford residents and Ole Miss students alike from taking advantage of the various options they have for a Sunday afternoon. If you’re in the mood for a sit-down dining experience, our go-to place is Mesquite Chophouse. At Mesquite, you’ll find some of Oxford’s best brunch food, alongside the BEST bottomless Bloody Marys and Mimosas. If you’re looking for something a little more casual, many of the bars do bottomless Mimosas and music, like The Cellar!

Sundays are definitely the day for indulgence, so why not shop around!? The Square is home to more boutiques than probably any other college town, and its no secret that these boutiques are the reason behind Oxford’s interest in fashion. You’ll find niche shoe stores (My Favorite Shoes), to casual t-shirt stores (Cat Daddy’s), to your typical trendy boutique (Miss Behavin). Whichever  you choose to go to, we want to warn you: you might not want to show your parents, husband, wife, or anybody else your credit card statement for the month.

As our afternoon is coming to an end, the last thing we recommend doing before dinner on your last night is taking an iconic Double Decker bus tour. It’ll give you a whole new perspective on Oxford, and you’ll get to see all that it has to offer.

*image from visitoxfordms.com

To conclude your stay, we’re going to have a typical Italian Sunday dinner at Saint Leo’s. The slender, New York City-style restaurant will give you a little NYC flare in the heart of the South. And, without a doubt, this is Oxford’s best location for pizza and the closest you’ll get to a New York slice! Hint: order your pizza extra crispy, then you’ll love it even more.

Now that you’re done with your itinerary for a typical weekend in Oxford, here are a college kid’s favorite seasonal events in Oxford, ranked from exciting (5) to a MUST experience (1) once in your life. You’ll have to plan a trip around these events, but they sure are worth it!

5. The Square’s Christmas Lights — Oxford residents call their town a “snow globe town,” specifically because of the lights put up during the Christmas season. They’re magical, to say the least!

4. Double Decker Arts Festival — Double Decker only comes once a year, but when it does, the state of Mississippi takes advantage of it. Actually, we don’t think we’ve ever seen more food trucks, art vendors, and people than we’ve seen at Double Decker… and the live band is just the icing on the cake!

3. Swayze Showers with Ole Miss Baseball — As Ole Miss students say “Swayze Showers bring may flowers!” For those who aren’t familiar with the tradition, whenever a home run is hit at Ole Miss Baseball’s Swayze Field, students throw water is in their red solo cup into the air. You may want an umbrella for this one, but Ole Miss beer showers are something unique to look forward to.

2. Oxford’s Saint Patrick’s Day Pub Crawl — While most Ole Miss students are on spring break, one of Oxford’s best kept secrets comes out: the pub crawl. The crawl, which has gained popularity in recent years, features seven Oxford bars and pubs on or around the square that can all pretend to be Irish for the day, just like us.

1. Tailgating in the grove for the Ole Miss VS. Alabama game — The rebels may not always win the game (though they definitely did in 2014 and 2015), but they always win the party! Party in the grove with fans, foes, and even cheerleaders before the game, then go cheer on the rebs (and pray for them, they need it) in the Vaught-Hemingway Stadium.


Written by Karly Trimble Photo Courtesy of University Communications/The University of Mississippi


  1. Bob
    April 16, 2019 / 1:14 am

    Great read

  2. Kristine Trimble
    April 16, 2019 / 1:30 am

    What a wonderful article ! I can’t wait to go back there and follow this itinerary!!!

  3. Jenn
    April 16, 2019 / 10:10 pm

    Sounds like a fun trip!! Great read.

  4. Kim
    April 16, 2019 / 10:22 pm

    Great read that gives Great detail for a well planned trip. Inspired me to add it to my list of future trips.

  5. Danny
    April 16, 2019 / 10:32 pm

    Been there and it’s a great place to visit! wish i read this article first

  6. Chas
    April 16, 2019 / 11:45 pm

    Having visited oxford once before, reading this article makes me want to visit again as soon as possible! Very well done

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    Incredible article. Can’t wait to visit

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  18. September 6, 2019 / 9:35 pm

    Now let s get to the important part FOOD. Three words: Big Bad Breakfast. Hands down my favorite breakfast of all time. I can t tell you how many (possibly hungover) Saturday mornings were spent here recalling Friday night s shenanigans on the square Or how many times my best friend Holland ( The Brunette Friend ) and I would hop in the car before class and chat over coffee and a delicious breakfast. I usually opt for the traditional Big Bad Breakfast and Cameron is a big fan of The Elvis sandwich. We always load up on their dangerously caffeinated coffee and fresh-squeezed orange juice. BBB is an Oxford staple and will always be one of my first stops when I come back to town!

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