The Ultimate Weekend in Lexington, Kentucky for a Sports Fan

Before you go

Two sporty days in Lexington

Day 1

Morning

• Order fried meat in the morning: Have breakfast at Winchell’s, because it serves fried bologna and eggs. Couple the dish with a screwdriver and point yourself at the TVs to watch your favorite morning sports show. Bonus points if you grab a seat at the bar and make some small talk (you will make more small talk here with friendly locals than maybe any other city in the U.S.).
• Try a new twist on tailgating: Keeneland’s race track opens at 7 a.m., and the first post time (AKA when races start) is 1 p.m. There is a big tailgate scene here on the weekends at “The Hill”—the races are shown on big screens and you don’t really even have to go into the park. Think of the tailgating scene at a college football game and add a healthy (but occasionally unhealthy?) obsession with sports betting. You should go into the track but also carve out some time to walk around The Hill just to say you did it.
• Take a stroll around the grounds: Very little will beat sitting in that 11 a.m. “it’s still morning” sun, watching the prep (the horses warming up, the grounds being watered, the general run-up to the races), and strolling around the park. Races run from 1 p.m. to about 4:30 p.m. on weekdays, and a little later on the weekends. Tickets range from $7 general admission on Wednesday and Thursday to $15 on the weekend.
• Educate yourself: If you’re new to horse racing, this is a great beginner’s guide. A full day at a park is very underrated fun—you can bet a $2 exacta on each race without a clue what you’re doing and still have a rooting stake. Final pro tip: go to an empty window (assuming you can find one) and chat up the person taking bets; they’re pros at helping guide rookies through the nomenclature and best-placing process.

Mid day

• Take a swing: Go check out Bible Mini-Golf, a unique place that combines religious fervor with physical activity. If it’s open, play all 54 holes. If it’s not? Take some pics of a truly different attraction. It’s an odd little find and locals embrace its quirk; even the owner is fine with whatever you think of it.
• Grab lunch at a college bar: Tin Roof, located right next to campus, gets rowdy at night but you won’t be disappointed if you go during the day. The sloppy nachos are as advertised and for a week after, you’ll be craving the cotija cheese in the street corn quesadilla.

Afternoon

• Taste Kentucky’s finest: Mirror Twin has a couple TVs, Wildcat-friendly patrons, and a fun set of beers with cool names and designs (if you’re a coffee head, try the Beanilla, a coffee bean lager).
• Go bourbon hopping: Next, I’d suggest jumping in an Uber and heading out to the Buffalo Trace Distillery—about a half hour from Lexington. If you don’t want to commit to a long journey, try Bespoken Spirits which has unique environmentally-friendly distilling practices or Fresh Bourbon, which has the distinction of being the first African American-owned distillery since slavery.
• Shop antique souvenirs: At the risk of sounding like an early retiree, there’s a lot of history here, with (specifically, but not limited to) horse racing traditions that are richer than almost anywhere else in the U.S. Try out Street Scene Vintage, where you’re going to find some colorful, old, interesting souvenirs including Kentucky gear from the '50s and horse memorabilia you won’t find anywhere else.

Evening

• Pay your respects to sports history: If you’re here during the basketball season, you should stop at nothing to go to Rupp Arena. Men’s or women’s game, just make the time. While you’re there, do not miss the swirl or vanilla ice cream. While the basketball experience feels spiritual to many, Kentucky football is an entirely different (ahem) ball game. There’s tradition here dating back to the late 1800s, but the team hasn't been especially good until recently. Still, a day out at a Wildcats football game gives you that full-on college gameday feeling. Even during the off season, there are a bunch of events that take place at the arena, from comedy shows to high school championship games. There are no official tours given, so the best you can do is stand outside and snap a photo if you can’t find an event to attend.
• Try the beer cheese: The Shamrock has a decadent burger made with homemade beer cheese and a cheese dip starter made with Guinness.
• Play a game: If tipsy singing is up your alley, Yesterday’s is perfect but you’re really there for the shuffleboard table and billiards.

Day 2

Morning

• Perk up before class: Get yourself caffeinated at Old School Coffee, which gets its name from being situated inside an old schoolhouse. It’s not just a gimmick, the coffee is great; try The Principal (white chocolate & hazelnut).
• Experience classic southern hospitality: Next, have breakfast at Josie’s. The spot is known for its pancakes but the food is done really well across the board and they pride themselves on hospitable service.

Mid day

• Imbibe in an old courthouse: Go have brunch at Carson’s—the Bloody Mary is maybe the best in Kentucky. Zim’s Cafe is also located in an old courthouse and is an experience you probably can’t get anywhere else (other than maybe, maybe Faneuil Hall in Boston). They also feature local artists, and now you can tell your friends you've gotten drinks in an old schoolhouse and an old courthouse.

Afternoon

• Get to know the horses you may have bet on: There are a lot of horse farms (though they’re often referred to as “thoroughbred” or “equine” farms) in and around Lexington and they encourage visitors. I recommend Old Friend Equine in nearby Georgetown, where you can visit retired Triple Crown horses. Take a few moments to check out the city, too—the Greek revival buildings here are really pretty.

Evening

• Eat in a church: Joe Bologna's Pizza (try the thin Sicilian pan varieties) is in an old church near Rupp Arena and has gigantic stained glass windows. It’s been there since the '70s and you can expect a large crowd before Kentucky games.
• Drink in an arcade: The Burl is the adult arcade you’ve been searching for. Drinks, pinball, Joust, bands… you will have a good time here.
• Close out at the oldest bar in Kentucky: End your night at the Chevy Chase Inn (not named after the SNL alum; it’s a nod to fox hunts and is connected, kind of loosely, to Henry Clay).

If you have three days

All of the above, but add...

• Louisville—and more importantly, Churchill Downs—is just an hour away. For those of you who have never been to a horse track, you might be caught off guard by how unassuming a track is when it isn’t on national TV. Buy some discounted julep glasses from years past, bet a few exactas, and maybe light up a cigar. Unless you happen to be here for Kentucky Derby weekend, consider yourself lucky you didn’t have to put on one of those hats. If you want to get historically grim while in Louisville, The Athletic did a great story last year on burial sites of some of horse racing’s most important figures.
• The Louisville Slugger factory (see bats get made, customize your own, breathe in baseball history), the Muhammad Ali Center (essentially a museum dedicated to the Louisville native), NuLu Whiskey and Whiskey Row (an entire district dedicated to the drink) are all excellent Louisville attractions. I’d also try to stop at North Lime Coffee and Donuts. It’s a funky, creative twist on your typical sweet breakfast treat; they serve savory sandwiches that replace bread in favor of donuts. And the pecan-crusted pork tenderloin at the Merrick Inn is fantastic.
• Walking Dead fans may want to check out Nic and Norman's—the Nic is Greg Nicotero and the Norman is Norman Reedus. There are a few of these, so it’s not like you’ll run into them in the kitchen (although you never know), but the Greg’s Pick burger is legit. The decor honors the two film buffs with photos of their time filming the show in the south; don’t expect a zombie restaurant!