Ihadn’t planned on visiting the bar first thing on arrival in Louisville, but with rain imminent — and an hour to while away until dinner — the Seelbach hotel bar lured me in.

Legend has it that the place also often beckoned St. Paul native F. Scott Fitzgerald — who, it was said, began writing “The Great Gatsby” on cocktail napkins there. His character, Gatsby, was even rumored to have been based on someone Fitzgerald met at the bar.

Whether that’s Louisville fact or fiction, who knows? I can only say that after a visit to this fetching, history-rich city, I came home with plenty of stories myself — as well as a strong urge to return.

Located on the Ohio River, and named in honor of the French King Louis XVI (which explains the fleur-de-lis symbol prevalent throughout the city), Louisville has long been known for its horse culture and Derby Day, bourbon and baseball. Today, the city itself has also evolved into something of a bon vivant, loaded with cutting-edge restaurants, varied cultural pursuits and trendy neighborhoods. In the 1920s, Fitzgerald wrote that Louisville was pervaded with a melancholy beauty. Nowadays its beauty is anything but melancholy.

Unless you’ve got a connection (or a lot of cash) for a seat at the annual Kentucky Derby, the best time to visit Churchill Downs is probably not during its annual “Run for the Roses,” according to my guide during the early morning “Barn and Backside” track tour I’d reserved for my first day in Louisville.

When I arrived at 6:45 a.m., the Churchill Downs parking lot was basically empty. In contrast, the barns I saw were bustling with activity: Handlers bathed horses, while water in the buckets created steam in the early morning light. Horses were being “hot walked” and still others were already on the track, “learning to be better racehorses,” according to our guide.

After the tour, I wandered through the adjacent Kentucky Derby Museum. Its treasure trove of Derby Day memorabilia includes videos of past races and a wall lined with fanciful hats worn for the occasion by celeb and local spectators.

Then I headed to Wagner’s Pharmacy. Located behind Churchill Downs, its proximity to the barns has made it a hangout of jockeys, grooms, trainers and sportswriters for years — not because you could buy horse liniment and pills so much, but because of its great lunch counter. Surrounded by sun-faded photos of past Derby-winning horses, I feasted on an omelet the size of a football and complimentary warm-from-the-oven blueberry muffins. On the way out, I overheard the pharmacist and a local as they exchanged racetrack pleasantries: “Well, we lost again … I can’t get a winner … but I’m thinking … ”

Louisville originals

That night at dinner, I learned of a Louisville legend who had picked a winner: In fact, the story goes that Jack Fry used two winning horse race tickets, each reportedly worth $10,000, to buy his restaurant. Opened in 1933 and once a haven for bootleggers and bookies, it’s now Louisville’s oldest free-standing restaurant. Photos of Jack and his wife, Flossie, adorn the walls. Present owner Stephanie Meeks told me that Jack is still around in spirit, too; the place is supposedly haunted. “Jack sits at the end of the bar every night, watching over everything.”

Jack Fry’s is in the city’s Highlands neighborhood, which has long been the most popular mecca for dining and shopping in Louisville.

Today, several other neighborhoods are being transformed into worthy destinations. One of the best is the East Market District. Dubbed NuLu (short for New Louisville), it’s minutes from downtown. Trendy places like Toast on Market and Harvest — both restaurants that showcase locally sourced ingredients — had waiting lines outside their doors. When I stopped at nearby Muth’s Candy shop (established in 1921) to buy a box of its famous Modjeskas (caramel-covered marshmallows created in honor of 1880s Polish actress Helena Modjeska), the clerk told me her old sweet-shop regulars were miffed because now they had trouble finding parking spots in the area.

With its antiques, artsy shops, a vinyl-record/coffee shop and even a beer store, I found plenty of other Louisville originals to buy in the NuLu district: jeweled horseshoes, beer made with bourbon, vintage julep glasses.

Bluegrass tunes

To hear some authentic bluegrass music — which I tracked down with the help of locals — I headed to the family-owned Darkstar Tavern, which features bluegrass on Thursday nights.

A true neighborhood bar in the Crescent Hill area, Darkstar is the kind of friendly place where someone greeted me with “Happy Thursday!” as I entered, and locals seemed to drift in and out amid the music. Relaxed and laid-back, the spacious spot was a mix of all ages, gray-haired oldsters and hip young couples. The music was excellent, and the roar and blur out the windows of an occasional train (the tracks were across the street) only added to its down-home appeal.

Most everyone there that night was drinking beer, which seemed to match the music and the mood.

I saved my bourbon sipping for the classy and beautiful Brown Hotel’s lobby at cocktail hour. There, I nursed an Old Fashioned (the bourbon-based drink was invented in Louisville, as was the Mint Julep), listening to a pianist playing pop love songs and recalling my visit to the new Jim Beam visitor center about 20 minutes out of Louisville.

From the traditional Brown, I headed to the hip Proof on Main restaurant for dinner. Adjacent to the 21C Museum Hotel, it’s easy to find; you can’t miss the mammoth replica of Michelangelo’s David that stands outside — just a few blocks from another giant Louisville icon — the Louisville Slugger bat. The bat leans against the front of the Louisville Slugger Museum and factory, a must-visit for kids of all ages.

The last night I was there, I drove to the historic St. James neighborhood. Lovely in the sunlight with its showpiece 1892 fountain and streets lined with charming Victorian era homes, it’s transformed at night by authentic gas lamplights on the boulevard. In the darkness, I loved how they cast shadows everywhere — flickering with romance, mystery and stories just waiting to be written.


Donna Tabbert Long writes about food and travel.