Photo by Katie Wheeler

Viva Lex-Vegas

For those who refuse to end their summer fun on Labor Day, there’s still plenty to be had in Lexington.

An easy, three-hour drive from Columbus, everything you need for one final blowout weekend is in Lexington, Kentucky: fantastic food and drinks—and betting on the best horses in the world.

After a couple days, it’s easy to see why locals call this Kentucky town “Lex Vegas.”

Never played the ponies before? No worries. The races are only half the fun. So let’s start with that other half:

When you get into town, belly up to the bar and get into the spirit. Start at the Bluegrass Tavern… and you might never leave. The dark wood and dimly lit atmosphere invite you to get comfortable and consider the bourbon list—which is a hefty consideration, at more than 200 deep. Skip the standard Jim Beam and Maker’s Mark; this is the place to find something rare and vintage. Too overwhelmed? Just ask for a recommendation. The staff knows their stuff. But be careful—it’s very easy to taste half a dozen bourbons before deciding on one.

For a bit of a trendier atmosphere, the place to be seen in Lexington is Belle’s Cocktail House. Belle’s is a busy spot for good reason. The drinks are first-class—clever concoctions all created from top-shelf liquor and fresh ingredients. Try a Belle Brezing – a vodka drink named after a once-famous Lexington madam. Keep your tab open, climb the stairs to the “lodge,” pick out a comfortable chair, and settle in. Belle’s is cool without being pretentious and is a great place to start and finish an evening.

Bourbon, like horse racing, is part of the Kentucky culture—and Lexington thrives on the pair. With eight distilleries in the area (including two downtown) – there’s enough bourbon in Lexington to drown in. Town Branch Distillery is a short drive from most any hotel in town. They offer tours and tastings of their three styles of house-made bourbon and single selection of rye whisky. You can also taste a number of craft beers, as they brew six different kinds. Town Branch is widely known for its Kentucky Bourbon Barrel Ale, a distinct beer finished in bourbon barrels that has developed a cult-level following.

For a taste of the top-shelf stuff, take a short trip outside Lexington to the Buffalo Trace Distillery in Frankfort—home of the sought-after Pappy Van Winkle. The 23-year-old small-batch version of this bourbon is so rare and sought-after that when 65 cases were stolen from the distillery a few years ago, bourbon aficionados went into a panic. A secondary market emerged where a single bottle could sell for $1,500 to $4,000. Seriously. (Ask any bartender in Columbus—Pappy is hard to find. If a store is lucky enough to get any in stock, it is usually gone before it hits the shelves. The Wine Guy in Gahanna can occasionally get a few bottles. The best bet is go straight to the source… or try the Liquor Barn in Lexington).

Imagine a Toys “R” Us for drinking adults and you’ve conjured The Liquor Barn—there’s no other way to describe it. Filled only with alcohol and party supplies, the Liquor Barn is a can’t-miss on your Kentucky trip.

Yeah, yeah, I hear you—even if you try to stick to a liquid diet, you’re going to have to eat at some point in the trip. Lexington’s got you… and the food is surprisingly chic.

Start the morning at Shakespeare and Co., which wins for its weird-cool atmosphere themed around its namesake. The eggs benedict and bloody mary will help remedy any questionable decisions from the night before. Downtown, the Village Idiot offers fare as eclectic as duck & waffles and as regular as a cheeseburger and fries. I highly recommend both—add a pint or two from the list of constantly evolving craft beer for a perfect experience.

Feeling fancy? Tony’s of Lexington is the epitome of a classic steakhouse. The wine list is extensive and heavy on international selections. Pick something red and order the nine-ounce filet. It is simple yet perfect. Tony’s also deserves praise for their service. I have walked in on Saturday nights late/early/with no reservations/with more people than planned and always been taken care of. You have no excuse—go there.

It isn’t a Portland-type hipster town, but the culinary scene in Lexington is definitely eclectic and forward-thinking.

And the crown jewel of a weekend in Lexington is a trip to Keeneland Race Course, one of the oldest and most picturesque thoroughbred race tracks in the world. Picture rolling green hills, century-old stone structures and patrons dressed to the nines.

But there is an edge to this place.

The traditional pre-party is more like a fancy tailgate than a cocktail hour. Partygoers play cornhole in the parking lots, slug beer and, of course, handicap the races.

Live racing is only held a select few days a year in April and October; however, during these short seasons, the best horses in the world are running at Keeneland. Check out Fall Stars Weekend, the season kick-off—Oct. 2-4.

Go Saturday, pre-party on the “hill” (a short walk from the main gate) or pick a spot in the paddock and get ready for a show. The first race is usually around 1:00 p.m., with a 10- or 11- race schedule. If you have never bet on the races, don’t worry – Keeneland has “Betalogists” posted around the concourse that offer basic instruction on how to read the racing form and place bets.

Picking isn’t easy—an “even money” day at the track is a good day—but you can’t win if you don’t play. The favorite will win 33 percent of the time, but a $10 win bet on a 50-1 longshot pays $500.

Just like Vegas, Keeneland wasn’t built on winners. Nobody expects to strike it rich at Keeneland, but they don’t play to lose either. Racing is serious in Lexington, and everyone has an uncle who “knows the trainer.”

But there is more to Keeneland than just betting on expensive horses, and the people watching is just as fun as the racing. Any Saturday will be a packed house of old money, regular joes, and University of Kentucky co-eds, all plied with bourbon and looking for a good time.

What separates a day at Keeneland from a Lane Avenue tailgate is that Lexington carries the Southern culture and attitude that differs a bit from what we are used to in Columbus. Picture Vineyard Vines vests and patterned belts, Ray Bans with croakies and a generally more buttoned-up demeanor. It sounds a bit stuffy at first, but by the third race and after a few drinks, all of a sudden the southern belles are bit chattier and the proper gentlemen are yelling at the horses as they race down the stretch. It does take a minute to get used to, but it’s well worth it.

While most of the day at Keeneland is spent roaming between betting windows and bars, great seats are available for the right price. And there is a section of Keeneland reserved for members only, more exclusive than courtside seats at Madison Square Garden: The Keeneland Clubhouse. The members-only group has a rumored 30-year waitlist and an initiation fee of $250,000. A little extra trivia for you: prospective members are told up front that their application might never get to the point of being considered.

On race days, Keeneland Clubhouse gentlemen must keep a jacket on at all times, and ladies are required to dress like, well, ladies. It is quite the spectacle, and worth a glimpse if you can get in as a guest. The only thing better than having a friend with a boat is having a friend who’s a Keeneland Clubhouse member.

For the football junkies who can’t miss a college game day, Keeneland accommodates. Lexington is home of the University of Kentucky, and Wildcat football is celebrated with Buckeye-like enthusiasm. And—yes, it gets better—on select days, a shuttle bus runs continuously from Keeneland to UK’s Commonwealth Stadium. The Keeneland/UK “Double,” a day at the track capped off with SEC football at night, is a fan favorite.

If you don’t visit for opening weekend, try October 31. This year, the Breeders’ Cup World Championships will be held at Keeneland. The Cup is the pinnacle of horse racing and the dream of every owner, trainer and jockey. The two-day affair of world-class racing will culminate with the Classic, a $5 million dollar race in which reigning Triple Crown champion American Pharoah (you might have heard of him?) will end his brilliant career. The final outing of a living legend makes it well worth the trip.

Bet the farm on him? I would—if I could.

But no matter when you visit Lex Vegas, you’ll be winning.

Martin Midian is a Columbus OVI/DUI attorney with thirst for adventure. Odds are 5-1 he’ll take another trip to Lexington this fall.