Tom Wilmes, Garden & Gun Contributor.
The international Thoroughbred community is set to descend on Lexington this fall, beginning in late October with the Keeneland Championship Sale (where the final auction item will likely be Castleton Farm, the landmark 951-acre estate dating to 1793), continuing with two days of top-shelf racing at the Breeders’ Cup World Championships, and wrapping up with the November Breeding Stock Sale.
It’s sure to be an exciting few weeks, and a day or two at the track sipping on bourbon is, of course, part of the plan (particularly at the Queen Elizabeth II Challenge Cup on October 10 and G&G’s Keeneland cocktail brunch on October 11). But as a Lexington native, I’m more looking forward to the autumnal rituals that can be found only here, like Lexington’s Thriller parade, the display of carved pumpkins on the steps of Transylvania University’s Old Morrison, and those fleeting few days when the ginkgo trees along Catalpa Road form a brilliant yellow canopy. Whether you’re in town for the bourbon, the horses, or a little of both, here are some of my favorite ways to enjoy Lexington this fall.
Make Downtown Your Home Base
Lexington’s major roads radiate outward like spokes on a wheel, putting most of the city within easy reach of its compact downtown. While there are a few unique outlying lodging options—the Kentucky Castle, an honest-to-goodness castle, is down Versailles Road from Keeneland—it’s tough to beat staying close to the action.
While the guest rooms at Marriott City Center can feel a bit austere, the property, which opened in 2020, has a lot going for it. It’s next to Jeff Ruby’s Steakhouse (grab a seat at the horseshoe-shaped bar) and directly above ItalX, where sangria, spritzes, and wood-fired pizzas are happy hour standouts. And a cocktail in the top-floor Infinity bar comes with one of the best views in town.
For funkier digs, there’s 21c Museum Hotel, which recently sold to a local hospitality group but still operates under the 21c banner. The Sire Hotel offers a quieter respite steps from Gratz Park, which is lined with stately homes.
For a livelier stay, choose the Manchester, a boutique hotel across from the new Gatton Park on the Town Branch and at the entrance to Lexington’s Distillery District. You could make an entire evening out of smoked old-fashioneds at the lobby bar; dinner at Granddam, helmed by Top Chef alum Paula Endara; and a tiki-inspired nightcap at the rooftop Lost Palm, all without leaving the building.
When you do venture out, there’s the extensive menu at Carson’s on Main Street, or the new Carson’s Back Porch directly behind it, where I enjoyed a trio of Connecticut-style lobster rolls on a recent visit. Dudley’s on Short, this yearcelebrating its forty-fifth anniversary, is an understated destination that never misses. If the weather cooperates, try for a table on the intimate rooftop terrace. Millstone is a short drive away, while the house-made pastas at Mileta make the trip out Nicholasville Road worthwhile. And plan ahead for one of the themed OMAGE dinners at the Apiary.
For Evenings Out
The Distillery District is one of several emerging entertainment areas that make for a convenient all-in-one option. If I’m headed to a show at the Burl, a concert venue located in a former train depot, I make sure to arrive early for an oversize slice at Goodfellas and a scoop of bourbon-and-honey ice cream from Crank & Boom. If bourbon is your thing, a visit to Dark Arts Whiskey House and a tour of James E. Pepper Distilling Co. are a must. At least pop into Pepper for an old-fashioned at the bar and hear how the historic brand ties into the cocktail’s origin.
Trivia night at Mirror Twin Brewing is one of my favorite ways to spend a low-key evening. It’s in the Warehouse Block, along National Avenue, where you’ll also find the Void Sake Company, Sav’s Gourmet Ice Cream, and the Willow wine bar, among other locally owned shops and restaurants. If I feel like stepping it up a notch, Epping’s on Eastside—and sister restaurant Coles 735 Main down the street—are both excellent options.
I’m also looking forward to nights out at the Commons, a new area taking shape just north of downtown. I’ve so far only had a cocktail at RD! Distillery, but judging from the view from its elevated patio of the Rail, a nearly completed music venue, with locations of OBC Kitchen and a Country Boy Brewing taproom and restaurant set to open this fall, I’ll be spending a lot more time here.
Take A Country Drive
Lexington is ringed by some of the most famous and productive horse farms anywhere. The best way to get behind the fences and into the barns is by booking with Horse Country Tours, but you don’t necessarily need a guided tour for a taste of what makes the area so special.
One of my favorite ways to spend a fall day is with a drive out Old Frankfort Pike to the Headley-Whitney Museum of Art, a jewel box of a museum currently displaying the Storied Quilts exhibit. Be sure to check out the shell grotto, where thousands of seashells and polished stones cover nearly every surface in elaborate patterns. From there, continue to Wallace Station Deli & Bakery. I’m partial to the Cubano and, of course, an ice-cold Ale-8. Eat at a shaded table out back or enjoy a picnic overlooking the scenic spillway at nearby Weisenberger Mills.
If bourbon is part of your agenda, this is also an easy place to fold in a visit to Castle & Key or Woodford Reserve, as both are within reach. Resist the temptation to turn the day into a distillery marathon, however. Reserving a tour at one and a tasting at the other is plenty, leaving time to browse the gift shops. I like to head into the small town of Midway for dinner at Heirloom or settle in for the four-course prix fixe menu at the always charming Holly Hill Inn.
Stroll Through Chevy Chase
An afternoon in the Chevy Chase neighborhood, just east of downtown, offers a taste of residential Lexington at its best. Start along Clay Avenue, where a collection of shops and boutiques gives way to leafy streets originally laid out by the Olmsted Brothers. Follow them toward Ashland, the Henry Clay Estate, and linger in the garden before heading to the shops, bars, and restaurants along East High Street and Euclid Avenue.
For a casual meal, there’s Bella Cafe and Grille. I celebrated a recent birthday with the tasting set at Omakase Sushi & Sake Bar, and Char has become a neighborhood favorite.
No matter where I’ve been previously, however, the best nights typically end at the Chevy Chase Inn. Founded in 1933 and Lexington’s oldest bar, it’s the kind of place where you stop in for “just one” and end up singing along to a live band with a dozen new friends.