Hey girls! Whether you’re checking out YesLouisville.com for help planning a lavish ladies weekend for Derby or you’re local & having guests in for the season, we don’t want you to waste one moment sifting through tourism guides, restaurant lists, or Facebook groups for recommendations!

So, we asked Nicole Stipp, co-founder of Matson & Gilman, purveyors of fine bourbon entertainment, to put together her ultimate guide to make the most of Derby Weekend in & around The Ville! We like to think we know a thing or two about our great state, but this list is so epic, we might just have to go for it ourselves!

Enjoy & remember to reach out to thank Nicole on the socials (@matsongilman) & check out MatsonGilman.com for the 411 on what fine bourbon entertainment entails!

Thursday:

Although nearly every day of Derby week will find the track full of visitors, Thurby still carries a lot of charm for us locals. We usually have the day off from work and it’s a great day to be at the track when it’s not in the millions.

Headed to the track?

  • Grab breakfast at Con Huevos: They’ve recently expanded, so we’re not guaranteeing it’ll be no-wait, but that french toast is worth it and their coffee will wake you right up from all the fun you had the night before.
  • Drink a strong coffee for the road & have a cookie at Please & Thank You. You can’t exactly pack a lunch for the track unless you’ve made some major clear-bag investments, so we like to be fueled and full before hitting up Churchill Downs.
  • Don’t have your hat yet? Swing by Revelry Boutique Gallery, Stag & Doe, or Work the Metal to snatch a good one, while still saving some money for bets at the track.
  • Once we’ve made it through the melee to get to the track, get seated and sip a congratulatory mint julep & spend the day laughing with your friends, looking at pretty ponies and trying your hand at some betting.
  • Getting out of the track can be a challenge at best, so we don’t recommend any reservations that you are going to sweat a timeline on. Instead, shake off the track at Hilltop Tavern after putting your name in for a table at the Silver Dollar. Hilltop has fantastic, inexpensive drinks and is always a fun crowd. And, there’s no better place for warming, spicy, delicious classics than the Silver Dollar. If you’re filled up on juleps, get your hands on their Gold Rush or a Hearts on Fire.
Evan Williams Bourbon Experience

Not headed to the track but want to feel the Derby Spirit?

  • STILL Grab breakfast at Con Huevos: We can’t understate the awesomeness.
  • BOURBON! One of our favorite tours for folks who are new to bourbon, or are bourbon lovers that don’t know a lot of history is the Evan Williams Bourbon Experience in Downtown Louisville. It’s a great starter tour and if you get your hands on Henry McKenna 10 Year Single Barrel these days, their gift shop might be the one spot in town you can find it!
  • Don’t want to GO to Churchill Downs, but still want to get into the ponies & Derby spirit? Head to Wagner’s Pharmacy which has been feeding horse trainers, horse owners & horse cheerleaders for decades. We thank the culinary gods for their fried bologna sandwich. You’ll be surrounded by years of Derby history, while not having to dive into the madness of Churchill Downs.
  • MORE BOURBON! After this near-Derby experience, head back to Main Street for an awesome tour and tasting at Michter’s Distillery at Fort Nelson. This distillery was a true labor of love and after your tour and tasting, enjoying a couple rounds at their bar is a great way to wind down your exciting day.
  • But, don’t wind down too much. Head to Copper & Kings, take the elevator to the third floor and hit up the rooftop patio for drinks and beautiful sunsets at ALEX&NDER. We love their sour & their Mexican Old Fashioned.
  • When it’s time for dinner, it’s Louisville and you have so many options. From Copper & Kings, you can go across the street to Lola above Butchertown Grocery and enjoy bar snacks in a luxe, speakeasy setting. If you want filling food that won’t give you a food hangover, walk a couple blocks and try the delicious, healthy offerings of Naive.
Bardstown Bourbon Company | Bottle & Bond Kitchen & Bar

Friday
All these folks in town clogging up the downtown streets & Interstate is the perfect excuse to head out into Bourbon Country. Always buy tickets to distilleries in advance as much as possible. It’ll speed up your check-in process and guarantee you actually get on a tour+tasting.

  • Invest in a driver or be very nice to one of your friends to be the sober driver, because it’s time to hit bourbon country!
  • Get up early and hit the road after some good breakfast sandwiches and strong coffee from Heine Brothers.
  • Drive out to bourbon Disneyland: Maker’s Mark. Enjoy a tour and tasting here, and then make your way to their excellent on-site restaurant, Star Hill Provisions. We love the husband-wife team behind this spot, with Chef Newman spitting out Kentucky classics with a twist and their bar serving up delicious bourbon slushies, classic cocktails & flights of Maker’s Mark products.
  • From Maker’s, get back on the road and head to Heaven Hill for a Connoisseur’s Tasting. After walking all over the Maker’s campus, it’s fun to go through this higher-end tasting experience just sitting in your seat in soaking in the Heaven Hill history. Most tastings here are lead by retired distillery employees, so they have stories — and tastebuds — for days.
  • Just a few minutes up the road from Heaven Hill, you can end your day with the excellent tour offered by Willett Distillery. We love their Seasoned to Perfection tour, which is shorter but focuses on the barrel mingling process and is a deep dive on why barrel location can make whiskeys taste so entirely different.
  • End your time in Bardstown at the Bottle+Bond Kitchen & Bar. Housed in the Bardstown Bourbon Company, this restaurant is serving up some culinary masterpieces and some truly delicious drinks. The last time we were here, our dinner lasted three hours. Not sure if it was the delicious food, the excellent service, the fireplaces or the flowing drinks, but this is a wonderful place to celebrate a hardworking day traipsing through bourbon country!
Castle & Key Distillery

Saturday

Woodford County and its surrounding environs is where a lot of the thoroughbreds that will be running in the Derby find their roots. Toast to their good health and victories with some great distillery tours and tastings.

  • Another early morning (don’t worry, you can sleep in on Sunday), will find you heading out to Woodford Reserve first thing Saturday morning. Fuel up with coffee from Heine Brothers on Eastern Parkway, and then go around the corner for a dozen fresh donuts from Nords Bakery.
  • From Nords, hop on the highway to Woodford Reserve and get on one of their early morning tours. Their gift shop always has some great Distillery-only bourbons, and since they are the bourbon of Derby,  you’ll find some great Derby collectibles there too!
  • Take a scenic drive through Woodford County for lunch at Chef Ouita Michele’s whistlestop outpost: Wallace Station. Delicious deli-style sandwiches made with tons of local, Kentucky products, and a cookie and sweets case that will have so smitten, you’ll be packing bags of them for the ride home.
  • After lunch, make your way to Castle & Key Distillery, where you can soak in the architectural wonder that is a 19th Century castle built to be a distillery, and after decades of neglect, is now producing gallons and gallons of delicious spirits each and every day. And, lest we forget, is being overseen by the first female Master Distiller in Kentucky since Prohibition, Marianne Eaves! You can join their full production tour or enjoy a shorter tour with an excellent sensory and cocktail experience in their Curated Cocktail Experience. Both of their tours are truly fantastic, with a knowledgeable staff, a beautiful grounds and a history steeped in some of the most prolific and important moments in bourbon’s history.
  • After your tour at Castle & Key, buy a round of cocktails (they serve wine & beer, too!) and a cheese board, snuggle up in the comfy, creekside Adirondack chairs and toast to a full day of sightseeing and bourbon drinking with your friends.
  • Once you’ve made your way back to Louisville, we recommend heading to NuLu. You can grab a high-end dinner at RYE or Wiltshire, or get great, simple food at Feast BBQ, Garage Bar or Galaxie. Once you’re in NuLu, you’re in the middle of great drinking and fun times. Slushies at Taj, margaritas at Galaxie, craft cocktails at Decca’s Cellar Bar. It’s all walkable and clustered together so you can grab rounds at bars all up and down Market Street.

Sunday

  • Sleep in, you’ve earned it!
  • Head to Couvilion for brunch, their patio is a great spot for a warm, sunny Sunday. They’ve got a super deal for bottomless mimosas ($12!!) and a brunch po’boy that will make you feel like you’ve dipped straight down to the Big Easy for breakfast.
  • You’re in Germantown, so make sure and hit up local green haven Forage for some plant-baby shopping and grab a latte at the Bean.
  • Once Sunday Happy Hour rolls around in Germantown, you’ll find everyone who is in the know enjoying delightful, $6 Old Fashioneds at The Pearl. If you’ve got the blues about your weekend coming to an end, these delicious drinks will ease your pain and bring about a fantastic end to your adventures!
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