Tupelo, MS, is one of South’s most fun small-town destinations, made even more exciting by its vibrant Cocktail Trail — a fabulous way to drink your way through the city’s charming downtown streets. We’re breaking down all seven stops on the trail (each within walking distance of the next), plus a few must-try bites to pair with your cocktails along the way!

Where to Start

Before you set out on the trail, be sure to pick up your official cocktail card at the Tupelo Visitors Center. Then, stop by each restaurant and order its signature cocktail. Once you’ve visited all the stops, return to the visitors center to receive a free #MyTupelo cocktail shaker! You can also snag a cocktail card at any of the participating restaurants along the trail.

Stop 1: Amsterdam Deli & Grill

Known for its authentic Mediterranean fare with an Italian twist, Amsterdam Deli & Grill is a popular eatery among tourists and locals alike. When you order with your Cocktail Trail card, you’ll receive The Jordan River, made with Tito’s vodka, champagne, lemon juice, and simple syrup. But don’t miss the restaurant’s extensive cocktail, wine, and beer menus if you have time to sit and stay a while.

Cocktail with lemon wedge on patio table.
Amsterdam Deli & Grill’s The Jordan River is a refreshing vodka-based cocktail perfect for patio weather.

If you’re ready for a bite, go for the pizza and flatbread selection. Popular choices include the Chicken Shawarma Pizza (shawarma spiced chicken, cheese, tomatoes, red onions, and garlic-based pita bread) and the Green With Envy Flatbread (a secret blend of oregano and sesame seeds with extra-virgin olive oil).

Stop 2: Downunder

Your next stop is Downunder, a restaurant and cocktail lounge that offers delicious international pub grub. Before heading to the bar’s nook with arcade games and darts, don’t forget to show the bartender your Cocktail Trail card. You’ll receive The Burnout, featuring bourbon, Grand Marnier, ginger syrup, lemon juice, ginger and grapefruit bitters, and a flamed orange slice.

Smoky cocktail with orange peel garnish.
Downunder’s Burnout is a smoky cocktail that’s the perfect combination of sweet and sour.

The extensive food menu offers a handful of appetizers, entreés, and sides. Standout items include “The Classic” Aussie Pie (a traditional Philly cheesesteak with butter chicken) and the Mahi BLT (blackened mahi with housemade remoulade, pickled onion, tomato, and cherrywood bacon).

Stop 3: Nautical Whimsey

Nautical Whimsey is Tupelo’s premier destination for delicious Italian and Cajun cuisine. We recommend snagging a seat on the restaurant’s patio to enjoy your meal. While the eatery certainly offers a sizable selection of wine, don’t miss out on its cocktails. Their official Cocktail Trail beverage is the Tupelo Martini with tequila, triple sec, sweet and sour mix, and blueberry syrup.

Popular dishes include toasted ravioli, build-your-own pizzas, a meat and cheese tray, and various soups and salads. But be sure to take a look at their Facebook page before your visit — they post regular food specials!

Stop 4: Fairpark Grill

Fairpark Grill is the quintessential classic American eatery, offering steak, seafood, and traditional bar fare. The interior is elevated, with a full bar and cozy booths. When you visit with your Cocktail Trail card, you’ll receive a Lemon Ice Box Pie Martini, made with Absolut Citron vodka, white chocolate, and freshly squeezed lemon juice.

The food menu offers something that’s sure to satisfy all taste buds. Standout items include the strawberry poppyseed salad topped with grilled chicken, a smokehouse pork sandwich, and mini Angus burgers. Be sure to end your meal with a slice of cheesecake or the wild berry cobbler!

SB Tip: Fairpark Grill also offers a delicious brunch menu on Saturdays and Sundays!

Stop 5: The Grillehouse

The Grillehouse has undoubtedly made a name for itself in Tupelo. The restaurant is the perfect blend of casual and fine dining and is primarily known for its steaks. However, the cocktail menu is sure to satisfy, too. The Kennedy is the restaurant’s official Cocktail Trail drink, which includes Knob Creek rye bourbon, Plantation dark rum, orange bitters, dark brown sugar, simple syrup, St. Germain, and an orange slice.

Male bartender serving Old Fashioned cocktail.
The Kennedy is The Grillehouse’s delicious twist on a classic Old Fashioned.

When it comes to food, entrées include ribeye, filets, and a variety of seafood. When ordering, note that two sides are included in the price listed on the menu to encourage guests to eat whatever they like. Standout sides include the smoked gouda mac and cheese as well as the blue cheese wedge with marinated tomatoes, bacon, and a sweet balsamic reduction.

Stop 6: Park Heights

Your next stop, Park Heights, is an excellent fine dining option. The main dining room’s hardwood floors and retro lighting provide an elevated ambiance without feeling too sophisticated. If you prefer outdoor dining, grab a table on the rooftop or patio as you enjoy your Cocktail Trail drink, the Tupelo Honey — honeysuckle vodka, elderflower, fresh mint, and lemon juice. For food, you can’t go wrong with any of the restaurant’s entrées. Standout entrees include the filet mignon, she-crab soup, and Springer Mountain brick chicken.

Restaurant bar area with tan chairs and blue accents.
The interior at Park Heights offers the perfect ambiance to enjoy a seafood-centered meal.

Stop 7: Jobos

Last, but certainly not least on your Cocktail Trail adventure, is Jobos. Located inside Hotel Tupelo (the city’s first boutique hotel!), the casual eatery is known for its authentic seafood and refreshing cocktails. The final beverage you’ll enjoy on the trail is The Daisy, which features Luna Azul tequila, triple sec, and freshly squeezed citrus juice with a Tajin- and herb-salted rim.

Once you’ve restored your appetite, we recommend starting your meal with the crawfish skillet mac and cheese. For entrées, we suggest any of the Jobos baskets, which offer everything from a crab cake sandwich to shrimp, a butter burger, and more. Other entrées include ginger-scallion noodles, grilled fish, and shrimp and grits.

Spread of entrées and appetizers on wood table.
Located inside Hotel Tupelo, Jobos is known for its seafood-centric menu and handcrafted cocktails.

Happy trails!

This article is sponsored by Visit Tupelo. All photography provided.

Brianna Goebel
About the Author
Brianna Goebel

Brianna is StyleBlueprint’s Associate Editor and Sponsored Content Manager. She is an avid fan of iced coffee and spends her free time reading all things true crime.