Visiting Lexington for basketball? Fancy, fast and unique restaurants near Rupp Arena

Yes, March Madness is finally here. And with it comes hungry basketball fans.

Many of those fans will be in Lexington at Rupp Arena for the first and second rounds of the 2025 NCAA men’s basketball tournament.

Eight teams — Louisville, Creighton, UCLA, Utah State, Tennessee, Wofford, Auburn, the winner of a play-in game between St. Francis and Alabama State — will battle it out March 20-22 on the home court of the University of Kentucky men’s basketball.

The University of Kentucky women’s basketball team is also hosting three first- and second-round games March 21-23 about a mile away at Memorial Coliseum. UK plays Liberty at noon March 21, followed by Kansas State taking on Fairfield. The winners of those games will play each other March 23.

And then next week, high school teams from across the state will head to Rupp Arena for the 2025 UK Healthcare Boys’ Sweet 16.

So where should you eat between all this basketball?

Here is a guide and list of 10 popular local restaurants near Rupp Arena, whether you’re looking for something fancy, fast or unique.

Fine dining downtown in Lexington

▪ Carson’s Food & Drink - On Main (362 E Main St): It’s wise to make a reservation for this popular dining spot. Opened in 2016, it has a rustic yet fancy feel with a menu to match. Highlights include grilled brie, soft shell crab BLT, Creole shrimp & grits and a variety of cuts of steak.

A must if you’re a brunch person and they have an extensive bourbon collection. If you’re willing to take a drive, they have a second location in the Andover neighborhood.

▪ Dudley’s On Short (259 W Short St.): Want to feel like you’re in the Horse Capital of the World without leaving downtown? Then this is the refined restaurant for you, a staple in Lexington since 1981.

Inside you’ll find the walls are lined with Thoroughbred pictures and paintings, while outside — if the weather cooperates — their patio is one of the finest in the city. Its Southern hospitality menu is a Buy Local Kentucky champion and changes with the seasons but its Pasta Dudley and KY Hot Brown are staples. Sundays feature a three-course supper for $40.

▪ Tony’s of Lexington (401 W Main St.): Across the street from Rupp Arena, the steakhouse is one of the most popular ones in Lexington, so make a reservation.

The extensive wine list is accompanied by a variety of prime steaks that can be finished with toppings such as Horsey Cream or Miso Truffle Butter. Sides are a la carte and shareable, but there is one item you cannot miss out on: the crab cake, considered by many the best in Lexington.

Quick eats in downtown Lexington

▪ Goodfellas Pizzeria (110 N Mill St.): You’ll find giant slices of New York-style pizza and breadsticks at this late-night pizzeria. Take-out only but worth it, especially after cheering on your favorite team and it’s within walking distance from Rupp Arena.

They have a special for a slice of pizza and a breadstick or salad. There’s also a location in the popular Distillery District if you want to sit, grab a drink from the bar and watch some of the NCAA games.

▪ Sam’s Hot Dog Stand (105 N. Limestone): “Hot Dog Headquarters” in downtown Lexington, Sam’s is known for their famous chili sauce and reasonable prices. Mainly open for lunch during the week and late Saturdays (9 p.m.-1 a.m.) to meet the needs of nearby bar patrons.

They also have turkey and veggie dogs, as well as Polish sausage and BBQ pulled pork. And don’t miss the homemade soups and house-made potato salad.

▪ Sawyer’s Downtown (140 W Main St.): This laid-back burger restaurant is a staple for downtown office workers. In the heart of downtown in the City Center block, the cafeteria-style hamburger restaurant is also known for its homemade chili.

And don’t forget the toppings bar to dress your burger any way you like. Mainly a lunch destination, owner Jim Sawyer often adjusts hours for big downtown events like the NCAA Tournament at Rupp.

Unique restaurants in downtown Lexington

▪ Big Blue Deli (144 W Short St.): The UK men’s team might not be in town, but visitors can still get a taste of the Big Blue Nation at this sandwich shop, which recently moved to a new location. The deli’s eight staple sandwiches reference the years UK has won a national championship.

The walls are covered in UK memorabilia, and if that’s not enough the deli has the seal of approval from UK basketball coach Mark Pope. In fact, you can eat like a Pope and get his spicy pastrami sandwich.

▪ Pearl’s Pizza (133 N Limestone): The intimate dining spot is known for two things: wood-fired pizza and bagels.

The pizza dough is part New York, part Naples. And the toppings are fresh as they come and always an adventure — ever had a sea scallop and bacon cream pizza?

They started to offer bagels to expand the menu and hours to include breakfast service during the pandemic. Salt, poppy seed, sesame seed and everything bagels are served with seven different spreads, plus there’s a breakfast sandwich menu. If you go for dinner, be sure to make reservations, because the dining room is small. Also, check out the wine and seafood options.

▪ Salt & Vinegar (102 W Vine St.): The German-American menu fits perfectly inside the Ethereal Brewing Public House. Chef and owner Greg Spaulding has built a following locally. His seasonally changing menus often follow his “old world cuisine, 21st century techniques” such as when he’s butchering a whole pig himself for pork chops, pancetta, bacon or bratwurst.

The restaurant has an old tavern feel, and the current menu is highlighted by homemade corned beef on a Reuben sandwich with house-made chips, beef short rib poutine and pork Schnitzel.

▪ Sidebar Grill (147 N Limestone): Looking for a dive bar with really good food? This is your place. Looking for what many consider to be the best burger in Lexington? This is your place. Need more convincing? The bar is popular with downtown regulars including lawyers from nearby courthouses as well as visitors from out of town, including, oh, the Foo Fighters.

The fires are hand-cut and thin, if that’s your thing. The black bean veggie burger is also a menu highlight.

This story was originally published March 18, 2025 at 9:03 AM.

Brian Simms

Lexington Herald-Leader

859-379-9041

Brian Simms has been with the Herald-Leader for 20-plus years, most recently reporting and editing coverage of restaurants, bars, food and bourbon. He is also a photographer and manages the newspapers photo archive that dates back to the late 1930s. Support my work with a digital subscription