Omni Louisville Hotel’s event spaces are anything but typical — think a speakeasy with bowling lanes, a marketplace packed with local vendors, and a library-inspired lounge with a fireplace.

My trip to Louisville started off strong — fitting for a city known for its potent libations. Just a couple of hours after landing at Louisville Muhammad Ali International Airport (SDF), I found myself wandering Churchill Downs, the 150-plus-year-old racetrack that, in just a few weeks, would host America’s longest continuously held sporting event, the Kentucky Derby. While about 250,000 spectators visit on the weekend of the big event, the other 51 weeks of the year are decidedly less hectic, making the historic site and adjacent Kentucky Derby Museum a winning off-site experience and venue for equine-loving groups — or just those who fancy donning a fascinator and sipping a bourbon while catching up with colleagues.

That’s exactly what my evening entailed. Old-fashioned in hand, I strolled the museum, pausing at the immersive “Black Heritage in Racing” exhibit and a create-your-own-derby-hat station, presented by Hatitude, before moving into the museum’s Great Hall for our group’s private dinner. With its tall ceilings and oval-shaped design, the space felt grand and theatrical — a perfect backdrop to watch “The Greatest Race,” an 18-minute film that brought the Derby to life on a towering, 360-degree LED screen, commanding our attention as we tucked into our meal.

The Derby isn’t the only major sporting event in town, though. Louisville draws many of them — like TFN’s Run 4 Roses Classic and Championship, the nation’s largest girls’ basketball exposure event, which has taken over the Kentucky Exposition Center since 2006. In 2028, Louisville will host the U.S. Olympic Gymnastics Team Trials, which will include a series of events at multiple venues over two weeks. Louisville’s event calendar is filled with more than sports, though. Just this year, for example, Ace Hardware Corporation brought its Spring Convention with 12,000 attendees to town for the first time, and in late August, the destination will host an estimated 8,000 participants at the American Legion National Convention.

A major reason why Louisville attracts this diversity of group business is that it offers not one but two convention facilities — the Kentucky International Convention Center (KICC) in downtown and the Kentucky Exposition Center, about four miles away, directly across from the airport. Two such large event venues for a city of this size, where the total population hovers just under 800,000, is impressive, and even more so when you consider the KICC underwent a total overhaul in 2018 and the Kentucky Exposition Center is in the thick of its own transformation — a two-phase project totaling more than $500 million that will soon make it the fifth-largest convention facility in the U.S.

Phase II of Kentucky Exposition Center’s expansion and renovation will wrap up in 2028.

The KICC was our first stop the next morning of our fam, hosted by Louisville Tourism, where over a breakfast of eggs and in-house smoked bacon, I learned about the hotel boom and new development reshaping downtown and beyond. The latest is Hotel Bourré Bonne, Curio Collection, which opened in 2025 across from the KICC. Next year’s opening of the JW Marriott Louisville and upcoming makeover of the city’s Humana Building into a 1,000-room convention hotel will significantly boost walkable room inventory around the KICC, which currently totals about 6,300. That includes modern convention properties from big-name brands like Hyatt Regency and Omni, my host hotel, as well as boutique properties with a history, like the Seelbach Hilton, which opened in 1905 and was a favorite of F. Scott Fitzgerald.

After breakfast, we crossed the street to see the newly revamped Louisville Visitors Center, where shelves of local memorabilia, cozy seating, and a custom bar make it particularly well-suited for a post-meeting mingling or tasting. It’s also a convenient jumping-off point to Fourth Street Live!, a neighboring pedestrian block packed with restaurants, bars, and live entertainment that just begs for a block party. What struck me most, as we explored, was just how compact and walkable it all felt.

Louisville’s Main Street is home to architecturally significant buildings built in the late 19th and early 20th centuries.

From the KICC, if you walk a block north toward the Ohio River, you’ll hit one of the city’s most popular stretches — Whiskey Row, once home to more than 50 flourishing distilleries that established Louisville’s claim to Bourbon fame in the mid-19th century. Also lining downtown’s Main Street is one of the country’s largest collections of cast-iron facades and Revivalist and Chicago School–style buildings. Today, you’ll still find plenty of bourbon experiences, from tasting rooms to working distilleries, but you’ll also be just steps from popular attractions like the Louisville Slugger Museum & Factory, Frazier Kentucky History Museum, and KMAC Contemporary Art Museum.

For lunch, we headed to Lou Lou on Market in NuLu, an arts district known for its street murals, galleries, and colorful homes. Easygoing and offbeat, NuLu is also well-suited for wandering — and it’s less than a five-minute Uber away from the KICC. Neighboring Butchertown, once a meatpacking district, also has plenty of diversions for a free afternoon — the city’s only brandy distillery, soccer games at the Lynn Family Stadium, and scores of mom-and-pop shops, like Work the Metal, a marketplace where I picked up a few gifts for friends. These neighborhoods are also ground zero for Louisville’s thriving bar and restaurant scene — like The Last Refuge, a restaurant, bar, and event space housed inside an old church, where we peered through the windows at the shelves packed with bourbon bottles rising more than two stories tall.

Back at the Omni, we treated ourselves to one more bourbon indulgence, naturally, in the lobby’s quiet library bar — a perfect place to savor another expertly made old-fashioned. I thought back on my whirlwind 24 hours as we toasted and sipped, and promised myself I would return, next time at a slower pace than a gallop.

Jennifer N. Dienst is senior editor at Convene