A boozy tour of Derby City

Ah, October. When the leaves start to change, the knee-high boots are broken out and Louisville’s first brisk autumn air creeps through the oak trees faster than you can say pumpkin spiced latte. From the St. James Court Art Show to the Jack-O-Lantern Spectacular at Iroquois Park, it seems as though there’s always something to do — some sort of mason-jar and mum-clad festival that we simply must attend. I found myself at this crossroads this past weekend, when I was given the responsibility of entertaining family in town for one day only. One day?! How on earth can I possibly show them the true gem that is Louisville in a matter of hours on a sunny October Sunday? A quick Google search points to all things token Lou: the Louisville Slugger Museum, The Big Four Bridge … nope, nope. We need something more organically Derby City, something with more oomph. We need, well, booze. 

When planning this day of epic autumnal proportions, I knew I’d like to hit a few different Louisville neighborhoods, to showcase to my cousins, Holli and Kelly, our fair city’s lovely diversity. We began with Sunday brunch in Anchorage at The Village Anchor. A tough decision it was, but what could possibly be better to soak up their delectable red velvet pancakes than a drink menu that boasts five different Bloody Mary cocktails? The Village Anchor Pub and Roost, while quite the hike for this Highlands dwelling bar maid, is nestled in the historic and affluent Anchorage neighborhood, and she truly flexes her brunch muscles for all guests to gaze upon. Nothing beats a stellar breakfast cocktail, and The Sultry Mrs. Robinson (champagne, St. Germaine Elderflower Liqueur, peach bitters-soaked sugar cube, orange) oozes seduction, just as its name implies. Can we just take shots of Mrs. Robinson all day? Frowned upon? All right, we’ll move on to our next locale, just as we’re getting nice and toasty. Pro-tip: Mimosas are $1 if you sit downstairs in The Sea Hag for Sunday Brunch. You’re welcome. 

For our next destination, I decided to head downtown with the fam and take my ladies to Proof on Main at 21c Museum Hotel. While 21c may pop up on every Thrillist or Yelp review on what to do in Louisville, that’s just because you can’t mess with perfection, and you certainly can’t fuck with a red penguin, so listicles aside, I simply consider it a must-see when it comes to entertaining out-of-towners. We grabbed four mimosas from the handsome bartender — rather, four glasses of champagne with a splash of freshly sqeezed orange juice, thanks darlin’ — and wandered around the glorious exhibits. Sufficiently buzzed is the perfect time to gaze upon somewhat controversial art and bond with family, don’t you agree?

What do you do when you’ve got a few hours to kill and your family isn’t ready to begin doing shots at Third Street Dive? How about a matinee showing of Dracula at Actors Theatre of Louisville? Actors Theatre is the only theater nationwide that shows the historic thriller annually, so chances are, if your guests are from out of town, they haven’t seen it. We popped in to see Stacey at the Actors Theatre bar (there’s also Edward Lee’s MilkWood restaurant, just below the theaters, but we were a bit pressed on time). Stacey poured us up some pinot noir we could take into the theatre with us, and we grabbed our seats. Dylan Chalfy dazzles and terrifies as this year’s Dracula, however, admittedly, Mark Bovino as Renfield was my favorite. He plays a wildly dramatic mental patient, and I was kind of drunk at this point, so it makes sense that I adored him. Can he just trounce around town in character whilst drinking with us?    

Next up: Follow me to Butchertown for a Sunday tour and tasting at Copper and Kings Butchertown brandy distillery. While Copper and Kings is somewhat new to Louisville, they reside in a historic Louisville neighborhood (great for parking and meandering up to East Market for, well, more drinks), and the rooftop deck offers a spectacular vantage point of downtown for a sunset sip, for anyone from locals to visitors. The bourbon barrel-aged brandy gives it quite the Louisville brand and was seemingly the perfect wind-down from a day of bouncing around Derby City. Tour guides were knowledgeable, and at only $12 per tour, I made away with a bottle of Vapor Distilled Lavender Absinthe ($60) for my home bar. Floral, aromatic, sweet, clean, boozy. Am I describing the Absinthe or my day of entertaining? You’ll never know. Neither will I, but one thing’s for certain: Nothing beats a Louisville sunset with a drink in hand, especially when the spirit was made right in our own backyard. That’s the organic Louisville autumn I’d showcase every day.