Tupelo, Mississippi

Tupelo, Mississippi

Cheers your way through the cocktail trail + more

Words by Riley Roberts 
Photos by Andrew Welch and the Tupelo CVB


When you hear Tupelo, your first thought might be Elvis—but there’s so much more to this Mississippi town than being home to the King of Rock ‘n’ Roll. In fact, you could fill your itinerary just by filling up your stomach! The food and beverage scene in Tupelo matches that of the South’s largest cities. The highlight of it all is Tupelo’s Cocktail Trail, a downtown loop of seven restaurant and bar destinations with drinks you’ll be dreaming of long after you return home. Get ready to grab a bite and have a cocktail (or seven) in Tupelo!

Morning Brews

Tupelo River

With two locations in town, Tupelo River is a startup that has taken the town by storm. Not only do they roast their own beans, but what may be more special is their partnerships with places like Hilltop Lavender Farm in Saltillo, Mississippi to create unique syrups in-house. You can also enjoy their baked good offerings from Talbot House, a local bakery dedicated to providing job skills training for women re-entering the workforce.

Strange Brew

Located in a former filling station, Strange Brew opened its doors in Tupelo in 2017. With a cozy and inviting atmosphere, the shop offers a wide range of specialty coffees, teas, and pastries to look delight the taste buds—plus every coffee comes with a complimentary chocolate covered coffee bean. 


Come for the coffee, stay for the skillet cookie. Crave’s famous skillet cookies take about 25 minutes to prepare, but you won’t mind hanging out in the vibrant café while you’re waiting. If you ever make it past the skillet cookie, you’ll be delighted to find cinnamon rolls, blueberry sausage biscuits, cheesecake, and more on their menu.

Lost + Found

Lost and Found Coffee is a coffeehouse that offers more than just your daily caffeine fix—they also host educational coffee workshops throughout the year. You can learn everything from home brewing techniques to the history and science of coffee—but no matter how much you learn, you’ll keep coming back to sample coffees from “The Lab,” where their baristas test unique flavor combinations. 

Cocktail Trail

Park Heights

A sophisticated wine bar and restaurant located in Downtown Tupelo, Park Heights offers a refined dining experience for wine enthusiasts and food lovers alike. Dine al fresco on the rooftop or the patio, and pair your meal with their signature drink for the cocktail trail, the Tupelo Honey—a blend of honeysuckle Vodka, elderflower, fresh mint, and lemon juice.


A trendy and vibrant restaurant, Jobos offers a modern coastal cuisine experience paired with creative handcrafted cocktails. The atmosphere varies depending on the time of day, with a relaxed and casual ambiance during brunch and a lively bar setting with a party vibe at night. Try their cocktail trail feature, The Daisy—made of Lunca Azul tequila, Triple Sec, and fresh squeezed citrus with a Tajin and herb salt rim.

The Grillehouse

Downtown Tupelo’s premier steakhouse, The Grillehouse serves up hand-cut, aged steaks cooked to perfection and gourmet appetizers and sides. Each bite at The Grillehouse is a celebration of flavor. Enjoy your steak with their cocktail trail drink of choice, The Kennedy—Knob Creek rye bourbon, Plantation dark rum, orange bitters, dark brown sugar, simple syrup, St. Germaine, and topped with an orange slice.


Make your way downstairs to the cool and casual Downunder. The eclectic spot features comfy couches alongside pinball machines and dart boards—the perfect spot for an evening hang. The food menu is just as delicious as the drinks, and the drinks are pretty fantastic. Start with their cocktail trail concoction, The Burnout—a mix of bourbon, Grand Marnier, ginger syrup, lemon juice, smoke, ginger/grapefruit bitters, and finished with a flamed orange.

Amsterdam Deli

This place gets busy, and after one visit you’ll understand why! Amsterdam Deli does bar food right, serving up crispy fried pickle chips and mouth watering sandwiches. Grab a stool at the bar and chat with one of the friendly bartenders while you try The Jordan River, their cocktail trail feature that combines Tito's vodka, champagne, lemon juice, and simple syrup.

Nautical Whimsey

A delicious blend of Italian and Cajun cuisine, Nautical Whimsey serves up savory dishes like Loaded Italian Fries and other local favorites. Crowds come for lunch and dinner, but evenings are the perfect time to try their cocktail trail special, The Tupelo Martini—a blend of Tequila, Triple Sec, sweet and sour, and blueberry syrup.

Fairpark Grill

An upscale dining experience with a laid back vibe, Fairpark Grill goes out of their way to make people happy. The menu is full of hits, but they're known for having the best burger in town. Their contribution to the cocktail trail is the dessert-worthy Lemon IceBox Pie Martini—combining Absolut Citron, white chocolate, and fresh-squeezed lemon juice.

More to Savor

Blue Canoe

The ultimate laid-back and funky joint in Tupelo, Blue Canoe is the city's home for live music like Gary Clark Jr. and Alabama Shakes. With over 100 beers available, including 35 on tap daily, this place is also a beer lover's paradise—and they’re a three time winner of the best dessert in Mississippi. Come for the music, stay for the beer.


A culinary gem, the Forklift menu showcases a fusion of Southern comfort food and modern flavors, creating a truly eclectic dining experience. Unique dishes like Jerk Steelhead Trout, Cider Braised Pork Cheeks, and Octopus will make you want to come back again and again. 

Connie’s Fried Chicken

Don’t let the name fool you—this chicken spot is a must-visit for breakfast… and not because of the chicken. Connie’s is known for their Blueberry Donuts, and every person that’s tried one will tell you it’s the best they’ve ever had. And yes, that includes the Good Grit team.