Louisville Weekend Trip: The Perfect 3-Day Itinerary

Bourbon distilleries. Steamboats chugging along the Ohio River. Horse racing. Welcome to Louisville, Kentucky, aka Derby City, aka Bourbon City, aka my beloved hometown! Spending a weekend in Louisville is just enough time to experience some of what this beautiful city has to offer – and I’ve created the perfect 3-day itinerary to convince all my friends to visit help you plan the perfect Louisville weekend trip.

Plus, I included a few extra itinerary ideas in case you’d like to extend your trip. So let’s go to Louisville, y’all!

Planning a trip to Louisville? Check out a few of these other posts:

 
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Louisville Kentucky Downtown Skyline
You’ll catch this view of the Louisville skyline on the first night of your itinerary, from the Big Four Bridge!

Louisville Travel FAQ’s

Here are a few things you might be wondering during the course of planning your trip to Louisville.

What’s the best time of year to visit Louisville?

The best time of year to visit Louisville is in late April and early May, during the Kentucky Derby Festival. The Kentucky Derby occurs on the first Saturday in May each year, and for 2 weeks before, the entire city comes alive during the Kentucky Derby Festival, with festivities all over town. (Psst: we’ve got a complete guide to attending the Kentucky Derby full of tips!)

But even if you’re not interested in horse racing, this is the best time of year to visit!

The city will be in full, glorious bloom; the weather is lovely (barring the occasional spring rain); downtown is decorated in colorful painted horses; and if you time your visit just right, you can experience everything from the largest fireworks show in the USA to a very slow race between two hundred-year old steamboats to celebrity-spotting on the red carpet.

That said, there is a downside: Derby Week, the first week of May, is also the most crowded and most expensive week to visit Louisville. So if you’re not into the shenanigans and excitement of the Kentucky Derby Festival, I recommend planning your trip between Mid May and late October.

Summer in Louisville is stunning: the city is lush and green, summer sunsets extend a golden glow until 9-10pm, and fireflies flicker in the grass on warm summer evenings. Sure, it can be hot and humid during the day, but Louisville is far north enough that it doesn’t get too hot – most summer days are in the 80’s.

Fall is the next best time of the year to visit. The crisp fall weather sets in around early October, and by late October, the leaves are turning brilliant shades of orange and red and falling on the Victorian homes of Louisville’s oldest neighborhoods. This is the time of year for haunted houses, carved pumpkin art, and ghost tours – check out our guide to things to do in Louisville in the fall for more.

Personally, I would advise against visiting Louisville in the winter, between November and March. It’s cold, but not usually snowy – kinda just grey and slushy and dead. We all tend to hibernate in the winter! But if you do visit in winter, prices will be low – just plan to spend most of your time indoors at bourbon distilleries and museums (we’ve got plenty of each).

How to get to Louisville?

Your best bet is to fly into the Muhammed Ali Airport (airport code SDF, long story). The airport is small but stacked with flights, especially on budget airlines like Spirit, Allegiant, Southwest, and Frontier. A direct flight to Louisville from about Denver all the way to the East Coast should only be about 2 hours. Coming from the West Coast, though, you’ll probably have a tougher time finding a short, direct flight.

If you can’t find a good flight, you might try checking flights to larger airports nearby, including Cincinnati (1.5 hours away) and Indianapolis (2 hours away). You’ll need to rent a car, of course, but if you’re saving enough money, it might be worth it!

Your other option is to drive in. Louisville is conveniently located about 3-5 hours from a bunch of other cities, including Nashville (3 hours), St. Louis (4 hours), and Chicago (5 hours). But they’re not, like, the prettiest drives? So in this case, the journey is not as good as the destination.

Is 3 days in Louisville enough?

Honestly, a regular weekend will be a bit tight, but if you can visit on a 3-day weekend, it’ll be perfect! We’ve packed our Louisville weekend trip itinerary all the way until Sunday evening, and we included a few extra ideas in case you’ve got time to extend your trip an extra day.

Louisville Kentucky Vacation Rental in Old Louisville, one of the best places to stay in Louisville
Many of our favorite places to stay in Louisville are in Victorian homes in historic Old Louisville. This is a vacation rental we love right off of Central Park!

Where to Stay in Louisville

There are tons of amazing places to stay in Louisville! But first you have to pick which part of town to base yourself in.

We recommend staying in or close to Downtown, such as in Old Louisville, NuLu, or Butchertown. Staying centrally will limit your need for a rental car, so you can get around to the entirety of this itinerary by bike, ride-share, and bus instead. Here are our picks in each area:

  • Downtown: Downtown Louisville has a bunch of awesome hotels within walking distance to Museum Row and the waterfront. We love Louisville’s newest boutique hotel, The Grady Hotel, right on Museum Row in the heart of downtown – y’all, it’s real cute! 21C Museum Hotel is both a hotel and a rad contemporary art museum. If you’re willing to splurge, 21C is super unique and well worth it! Fun fact: there are 21c locations in other cities, but Louisville is the original location.
  • Old Louisville: This historic neighborhood is Louisville’s most beautiful, and is full of gorgeous Victorian homes. If you can snag it, our favorite Louisville vacation rental is right on beautiful little Central Park! Or try The Inn at St. James Court, a charming b&b located on Louisville’s beautiful and walkable St. James Court.
  • Butchertown & NuLu: These are two of the most up-and-coming neighborhoods in Louisville, turning old historic warehouses into cool urban-living lofts, galleries, and eateries. They’re fantastic walking and bike-friendly neighborhoods, but you won’t find many hotels – so we recommend booking on VRBO! We love this chic, hip loft that’s one street over from the shops and restaurants on Market Street. This colorful, historic apartment is right next to the NuLu Marketplace, and this vibrant apartment is just one block away from our favorite coffee shop, Quills.

One more tip: Louisville has lots of great hotels, but unfortunately, many of them are in the East End – a part of town that’s not actually great for visitors and tourists. It’s not accessible by public transit, it’s mostly residential, and it’s far away from the best things to do in Louisville. The reason so many hotels are in this area is that there’s lots of space and it’s near a few business parks. We don’t recommend staying in Louisville’s East End.

Want some more options and tips on where to stay during your trip? Head over to our detailed guide on where to stay in Louisville!

See also
Where to Stay in Louisville, Kentucky (and Where NOT to): a Local’s Guide

Louisville Weekend Trip: Friday

You’ll arrive in Louisville on Friday afternoon and head to Old Louisville, Louisville’s most beautiful and historic neighborhood. Depending on how early you arrive, you’ll try a Louisville specialty for lunch, then explore the beautiful neighborhood of Old Louisville on foot until dinnertime and before tucking into an incredible multi-course meal at one of Louisville’s best restaurants.

Lunch at Buck’s

If there’s one dish that Louisville is known for, it’s a Hot Brown. So if you can arrive early enough on Friday, you’ll be able to head to one of the best places to get it: Buck’s in Old Louisville.

What is a Hot Brown, you ask? A Hot Brown is a warm, baked open face sandwich consisting of a piece of bread topped with with turkey, tomato bacon, and creamy, bubbly, cheesy Mornay sauce – and it was invented at the Brown Hotel in downtown Louisville. Supposedly, the inspiration for the Hot Brown came from the Hotel’s swinging dance parties. We love this theory because it is fabulously reminiscent of a beloved Louisville-starring classic, The Great Gatsby (although F. Scott Fitzgerald actually has closer ties to the Seelbach Hotel!)

Anyway, the dish is best known as Louisville’s most famous culinary creation. (Ahem: if you’re thinking about a certain fried chicken chain that happens to be headquartered here, you can push that thought right out of your mind.)

At Buck’s, you can sit outdoors in the garden or dine in the fabulous lounge. With its black and white tiled floors, live piano music, clearly-very-old bar, and lush interiors, you’ll feel like you’ve been transported back in time. It’s a fairly formal place, but nobody will judge you if you’re not dressed up. (Though if you came from Churchill Downs this morning, odds are you’ll be dressed perfectly.)

See also
13 Famous Louisville (and Kentucky) Foods You Have to Try
Local Travel Tip: The best way to taste the best food in Louisville is on a food and history walking tour with Louisville Food Tours! Explore the story of Louisville and Kentucky while tasting culinary classics like bourbon balls, biscuits, fried chicken, and - of course - bourbon! You can book a tour on FareHarbor or Viator.

Explore Old Louisville

Old Louisville is the most beautiful neighborhood in Louisville, and exploring the neighborhood’s historic streets is absolutely a highlight of any visit to Louisville! The ornate Victorian mansions (the largest collection of them in the world!), flickering gas lamps, tree-covered streets, flickering gas lamps, and fountains of Belgravia Court and St. James Court are picture-perfect. Walking paths wind through the historic homes, and at the center of the neighborhood is the small but charming Central Park.

This is where you’ll spend your afternoon. We recommend taking a historic walking tour of Louisville to learn all about the area and its storied past, or doing a self-guided tour.

But aside from gawking at the beauty of it all, here are a few activities we recommend for your Sunday afternoon:

  • Tour a Victorian mansion/castle at the Conrad-Caldwell House Museum: Step back in time to the Victorian grandeur of Louisville’s Gilded Age. Constructed in 1895, the Richardsonian Romanesque castle is one of the most unique mansions in the Old Louisville neighborhood, which itself is home to America’s largest concentration of Victorian homes. The home has been beautifully preserved, and you may just get a personalized tour from a docents who is a direct descendant of the former owners.
  • Enjoy modern art at the Speed Art Museum: Located adjacent to the University of Louisville’s campus, the Speed Art Museum is the oldest, largest, and foremost museum of art in Kentucky. Called one of “The World’s Most Beautiful New Museums” by Travel & Leisure Magazine (the building is rad, seriously… you should visit just for the selfie) the museum features rotating exhibitions on a diverse array of ancient, classical, and modern art. As a bonus, the museum is free to visit on Sundays!
  • Get a craft beer at Old Louisville Brewery: This cozy local brewery, located in a converted Victorian, reflects the neighborhood perfectly: worn, tall dark wooden booths and patchy layered walls expose all the history of the building. Grab a glass of their flagship Kentucky Common, an almost extinct beer style made from bourbon mash grain.

Dinner at 610 Magnolia

Located conveniently across the street from Old Louisville Brewery (almost like we planned it that way?!), 610 Magnolia is not so much a restaurant as it is an experience. I hope you saved room at lunch, because you’re going to be enjoying a delicious 4- or 6-course tasting menu!

Helmed by Louisville’s own celebrity chef, Chef Edward Lee, The food at 610 Magnolia is an unexpected combination of flavors, culture, and ingredients – it definitely isn’t your typical Southern fare. Chef Lee aims to put ALL of Louisville – historic and progressive, diverse and complex – on a plate. Depending on the day, you might get tempura fried okra or Chawanmuski with fried oysters. Keep an open mind – and be sure to make a reservation, like, way in advance.

By the way, if Chef Lee’s name sounds familiar, maybe you saw him as a guest judge on Chopped, or competing on Top Chef, or hosting The Mind of a Chef – he’s kind of a big deal. (We’re very proud!)

  • Travel Tip: Visiting Louisville during the summer? One of the best local summer events is the long-running Kentucky Shakespeare Festival, which produces 3 Shakespeare productions each summer outdoors in beautiful Central Park in the center of Old Louisville. Attendance is free, the production quality is incredible, and it’s one of the best ways to spend a summer evening in Louisville and get acquainted with Louisville’s fantastic theatre scene!
See also
The 26 Best Louisville Breweries (and Southern Indiana, too)
Clock and Street View in Downtown Louisville Kentucky
Welcome to the historic facades of downtown Louisville. Psst: Look for this picture in the airport when you arrive – it’s one of my favorite Louisville life achievements!

Louisville Weekend Trip: Saturday

Today you’ll be exploring downtown Louisville and its adjacent neighborhood NuLu, hopping into museums and touring bourbon distilleries.

You’ll definitely be drinking today, but don’t worry, you won’t need a car: the free LouLift bus will take you everywhere you need to go today. It runs up and down Market and Main streets until 6pm, every day except Sunday.

Depending on where you’re staying, you can leave your car behind and take a LYFT to and from your accommodation – or, find parking in NuLu or downtown and leave it all day!

Brunch at 21C

You’ll begin your Sunday with a bougie brunch at Proof on Main, the unique restaurant in Louisville’s famous 21C Museum Hotel! The restaurant every bit as quirky as the hotel/modern art museum it’s located inside of. Redecorated regularly with its own series of installations, the restaurant is a museum in its own right. Oh, and the food is magnificent.

Start your day off properly with a French Toast Casserole made with apple butter, whipped cream, and fresh hazelnuts, or a Cast Iron Dutch Pancake with blackberry maple preserves, cultured butter, and cocoa nibs.

And because you’re in the South (sort of) and it’s totally acceptable to drink at brunch, order a Relancer, made with dolin blanc, apricot liquoer, lemon, thyme, and “bubbles.” I don’t know exactly what half of those ingredients really are, but trust me, it’s delish.

Once you’re thoroughly satiated, take a stroll through the modern art museum part of 21C. But don’t spend too long: this morning is all about museums, and there are lots more of them to see in this stretch of downtown, which is known as Museum Row!

Museum Hopping & Bourbon Tasting on Museum Row

West Main Street is my favorite part of Downtown Louisville: it’s gorgeous and historic, with blocks of well-preserved beautiful old brick facades.

This stretch of downtown is also known as Museum Row, and its home to a plethora of excellent museums. Stroll along and pop into anything that strikes your fancy! Here are a few museums that we recommend:

  •  The Frazier Kentucky History Museum: At Museum Row’s excellent history museum, you’ll dive into local history. You’ll learn about the story of bourbon, the role of Kentucky in the Civil War and the Lewis & Clark expedition, and the complex story behind Louisville’s segregated and redlined West End. The museum also houses a large collection of historically significant artifacts of American, American Indian, Asian, and European origin. Pick up your ticket online to skip waiting in line at the door!
  •  Louisville Slugger Museum & Factory: Louisville sluggers, perhaps the greatest contribution to baseball ever (you’re welcome everyone), are made right here in Louisville at the Slugger Factory! Take a tour of the Louisville Slugger factory to see the bats being made, try your hand at the batting cage using bats from famous baseball stars, and walk away with an awesome souvenir: a mini Louisville Slugger bat! Finding the museum is easy: just look for the world’s largest Baseball Bat. It’s 120 feet tall.
  •  (KMAC) Love contemporary art and craft? KMAC Museum “explores the relationship between art and craft by identifying art as big idea and craft as the intersection between process, materials and labor.” You might find a contemporary art exhibit woven from cloth, or crafted from clay, or blown from glass. As a bonus, entry is free to all students and youths 18 years and younger!
  • Muhammad Ali Center: This museum – located about a block off of Museum Row – explores the life and legacy of Muhammad Ali, one of Louisville’s most famous residents. Co-founded by Ali himself during his lifetime, the museum is as honest as it is informative, expanding beyond Ali’s illustrious boxing career and examining, with a critical eye, the man himself – with all of his flaws – as well as the racist and conflicted society from which he emerged.

Sprinkled in between the museums, you’ll find a trick to making museum-hopping even more exciting: bourbon distilleries!

See also
The 25 Coolest Things To Do in Louisville in Summer

the Evan Williams Experience in downtown Louisville Kentucky
Although not technically a distillery, the Evan Williams Bourbon Experience: is definitely unique and involves a full time-traveling situation, with an actor in full costume serving drinks in an underground Prohibition-era speakeasy.

There is no shortage of distilleries in Louisville, and in fact, there are 3 fantastic bourbon distilleries located on or just off of Museum Row:

  • Mitcher’s Fort Nelson Micro-Distillery: Descending from one of America’s oldest whiskey companies, this small distillery right on Museum Row makes rye, whiskey and bourbon. Take a Discovery Tour for a one-hour overview of the Mitcher’s distilling and barreling process along with a 5-sample whiskey and bourbon tasting. This is most conveniently located on Museum Row – it’s right across from the Slugger Museum and next to the Frazier Museum!
  • Kentucky Peerless Distilling: About a 5-minute walk away from Museum Row, this distillery has been distilling bourbon and rye whiskey since the 1880’s, including a much more modern absinthe-finished rye (yum)! Book a 45-minute guided tasting experience, a 1-hour behind-the-scenes grain-to-bottle distillery tour and tasting, or if you fancy, a private VIP tour tasting in the onsite speakeasy.
  • Evan Williams Bourbon Experience: Although not technically a distillery, this bourbon tasting ~experience is located at the end of Museum Row and is definitely unique. Their Traditional Tour & Tasting includes four bourbon samples, but if you’ve got a little more time, the Speakeasy Tasting Experience involves full time-traveling situation, with an actor in period costume serving up drinks in an underground speakeasy that feels straight out of Prohibition.

Travel Tip: The Main Ticket is a single admission ticket that will let you into most of these museums and two bourbon distilleries for a one-time price of around $50. The more museums and distilleries you visit, the more you save! Pick one up here.

See also
9 Distilleries in Louisville, Kentucky: from Bourbon to Brandy

Lunch in Downtown or NuLu

You’ve got a choice here: you can either eat at one of the excellent bourbon bars along Whiskey Row (and pop into one more bourbon distillery), OR you can hop on the free LouLift bus to take you into NuLu for lunch, where you’ll be spending the afternoon.

Option One: Whiskey Row

Whiskey Row is a stretch of West Main Street located a couple blocks down from Museum Row. It’s lined with well-preserved historic facades which house several of the best bars on the Urban Bourbon trail – and some of the best food in Louisville, too!

Take your pick from one of these two restaurants, located across the street from one another:

  • Doc Crow’s Southern Smokehouse & Raw Bar serves up delicious food alongside a plethora of bourbon. Order the pimento beer cheese & chips to share, anything from the onsite smoker, a mint julep lemonade, and a slice of real Derby Pie™ for dessert.
  • Merle’s Whiskey Kitchen: If you can’t help putting on a Southern Accent here, it’s understandable. This cuisine is Southern AF. We’re talkin’ fried chicken, cornbread, mac and cheese, candied bacon, sweet potato casserole, the workds. Somewhat surprisingly, there’s also a great plant-based menu selection, too! Plus, of course, lots of bourbon options, including a selection of hand-picked reserve barrels.

While you’re in this area, there’s an extra museum and an additional bourbon distillery to visit:

  • Old Forester Distilling Co.: Next to Doc Crow’s and Merles, Old Forester has been on Whiskey Row since 1870. Five generations and 150 years later, you can tour the distillery to see fermentation, distillation, barrel making, maturation and bottling – plus, of course, a tasting.
  • Roots 101 African-American Museum: This recently opened museum a couple blocks from Whiskey Row promotes understanding and appreciation of the achievements, contributions, and experiences of African American history, culture and art. Exhibits range from coverage of Louisville’s history of racism and activism to the untold stories of the Benin Empire.

Option Two: NuLu

Our selections in NuLu are cheaper and quicker than the options we recommended on Whiskey Row. So if you’re short on time, hop on the LouLift and head to one of these quick-service Louisville staples:

  •  Biscuit Belly: NuLu’s delicious Southern style biscuit-sandwich eatery makes 3 different, delicious gravies. Order a “Gravy Train” to try them all and appreciate the excellent pun. We recommend the Mama’s Boy, which pairs buttermilk chicken with roasted jalapeños, pimento cheese, crunchy pickles, and a fried green tomato. In addition to incredible biscuit sandwiches, we also recommend ordering some Bonuts, biscuit donut holes served with bourbon cream cheese frosting or chocolate gravy.
  • Feast BBQ: Head here for a deliciously moist pulled pork sandwich and buttery toasted bun. But our favorite menu item are the pork cakes, which are similar to a crab cake but made from pulled pork (a Louisville culinary creation), served with a mouth-watering sorghum syrup and crunchy coleslaw.
  • Royals Hot Chicken serves up Nashville style hot chicken: deliciously crispy on the outside, juicy on the inside fried chicken that isn’t your normal fast food fare.

If you saved room for dessert, head to Louisville Cream  for incredible ice cream featuring flavors like roasted peaches, bourbon smoked pecans, and mascarpone swirled with homemade strawberry jam.

Explore NuLu & Tour Bourbon Distilleries

You’re officially heading from West Main Street to East Main Street! This up-and-coming side of Main is an extremely hip neighborhood with an extremely hip name to match: NuLu, aka “New Louisville.”

Here you’ll find colorful murals, delicious food, locally-owned shops selling artistan-crafted wares, a marketplace, eclectic galleries, and of course, bourbon distilleries.

Listen: prepare your livers, because this is Bourbon City. So yes, in case your morning bourbon tastings weren’t enough it for you, we’re gonna pile on two more just to keep it fun.

  • Psst: Need an afternoon pick-me-up? Two of the best coffee shops in Louisville are in NuLu, Quills and Please & Thank You. The latter is best known for its chocolate chip cookies, so save room because they are the best in Louisville, in Kentucky, and I truly believe the country, too.

But there’s much more to do in NuLu than drink! So before or after your distillery tours, check out these local spots:

  • Muth’s Candies: This iconic candy shop has been here since 1921, long before “NuLu” existed.  Muth’s is known for two famous Louisville confections: delicious Modjeskas, a soft caramel with a chewy marshmallow center; and with bourbon balls, a quintessential Louisville treat made with pecans, chocolate, and bourbon cream that you cannot leave town without trying.
  • NuLu Market Place: This indoor market is filled with restaurants, shops, breweries, and bars all bordering a charming courtyard.
  • Revelry: This boutique and art gallery sells eclectic gifts hand-crafted by local artists. Browsing here is a treat, and you can find everything from jewelry to art, stationery, stickers, tea towels, and wall prints – many of which are Louisville or Kentucky-themed! This is one of our favorite places to shop for Louisville souvenirs.
  • W.O.W Women-Owned Wallet: This feminist gift shop exclusively sells products created by women-owned companies.
  • BLōFISH: This locally owned, gender-neutral clothing line and boutique is also a B-Corp. Not only are their LGBTQ+ positive and trans-friendly clothes ethically produced, but the proceeds support a wide variety of social justice causes.
  • Hazel & Hunt: This travel-inspired, locally-owned shop offers beautifully designed products from tees to sweatshirts, and is a great place to find cozy Louisville-themed swag.

When you’re ready, take a short stroll over to Rabbit Hole Distillery. During the one-hour guided tour of the contemporary, industrial-chic distillery, you’ll learn about how grains are transformed into whiskey, how Rabbit Hole’s philosophy is changing the bourbon industry, taste a 4-grain Kentucky Straight Bourbon, and end at the Overlook lounge for a generous bourbon tasting with a view.

After your tour at Rabbit Hole, walk 7 minutes over to Angel’s Envy, a small batch bourbon distiller that specializes in finished bourbon. A finished bourbon is created by aging bourbon twice: after the usual aging process, Angel’s Envy bourbon is then aged in port barrels. The end product? A deliciously complex bourbon, perfect for both sipping and mixing into cocktails.

You can a full tour of the gorgeous Louisville distillery along with a bourbon tasting, or the shorter Sensory Tour, which also includes a bourbon tasting (and chocolate, too).

See also
The NuLu Neighborhood Guide: Where to Eat, Drink, Play and Stay

For dinner, dine at Decca in NuLu, an upscale restaurant with phenomenal food. We recommend the charred octopus!

Dinner & Drinks in NuLu

For dinner, dine at Mayan Cafe. Mayan Cafe has been making bellies happy for 20+ years, and offers an intimate dining experience centered on Mayan cuisine crafted with locally sourced, sustainably farmed, and seasonal ingredients. Order their fresh ceviche and Cochinita Pibil, made with local pork, achiote sauce, and their famous lima beans and rice – anyone that has had them will tell you that the lima beans are roasted to perfection :chefs kiss:.

In the mood for something a little more laid back? Head to Garage Bar, a hip gastropub in a converted mechanic garage, to eat wood-fired pizza, artisan cured meats & cheeses, and local farm to table fare on their spacious outdoor patio.

After dinner (if you’re not exhausted from drinking bourbon all day, that is) head to space-themed Galaxie bar for incredible craft cocktails and to dance the night away!

Entrance to Churchill Downs with horse statue and flowers in Louisville Kentucky
Welcome to Churchill Downs!

Louisville Weekend Trip: Sunday

On the last day of your Louisville weekend trip, you’ll visit a famous Louisville institution and learn about the history of the Kentucky Derby. In the afternoon, you’ll tour Louisville’s modern art museum, stroll across the Ohio River, and have dinner at a delicious brewery in southern Indiana with a stunning view of the Louisville skyline.

Breakfast & Churchill Downs

You’ll start your Sunday with breakfast and a visit to Louisville’s iconic twin steeples at Churchill Downs. But before you don your fanciest hat and order a Mint Julep, let’s take a moment to discuss something incredible important: is horse racing ethical?

I don’t have a quick answer for that, though I do recommend reading this incredibly detailed article in the New Yorker which looks at this question from all angles. The easiest and quickest answer I can give you is that it depends – mostly on the horse’s owner, jockey, and trainer, as well as the guidelines at each specific track and the industry standards.

Although horse racing has long been a tradition here in Kentucky, we are at a pivotal moment in the history of the sport. The horse racing industry is facing well-deserved criticism and pressure to improve their requirements, and in the last couple of years, several new regulations have gone into effect with the goal of protecting the horses. The biggest change is implementation of the Horse Racing Safety & Integrity Act – here is a helpful article which breaks it all down.

Horse injuries and deaths occur when horses are pushed beyond their physical limits, given drugs to enhance their performance, or a track is not properly maintained – none of that is ethical, and it’s not OK.

That said, the fact is that horses do love to run, and a well-loved horse creates an incredibly strong bond with its jockey and trainer – which is also good for racing performance. And when a horse is injured or dies, it is heartbreaking – for animal lovers in general, but especially for those closest to the horse: their jockeys, trainers, and in certain cases, owners. In a perfect world, only horses in perfect health and at appropriate ages would be allowed to race, and I’m hopeful that the stricter regulations in place will move the horse racing industry in the right direction.

So: if you’re ethically comfortable with it, today you’ll be visiting Churchill Downs and the Kentucky Derby Museum. But before we dive into today’s plan, I do have a caveat: you may need to adjust today’s itinerary depending on the time of year you’re visiting! It’s a bit confusing, but I’ll walk you through it.

See also
12 Lakes Near Louisville, Kentucky (for Swimming and Boating)

Mint Julep at Churchill Downs in Louisville Kentucky

Visiting Louisville during Derby Season

During Derby Season – the last week of April and first week of May – you have the opportunity to experience a unique and exciting Derby week activity: Dawn at the Downs! This is when jockeys and horses are warming up first thing in the morning.

For aspiring betters and folks with lots of money on the line, this is a good opportunity to make important decisions about which horses to bet on based on their morning warm-up performance. For the rest of us, it’s a good opportunity to spot celebrities and see horses on the festive Kentucky Derby grounds – for free!

You’ll want to head to Churchill Downs first thing in the morning. Derby and Oaks contenders begin first around 7:30 AM, but you’ll find horses warming up until 10am. You do not need a ticket!

After you’ve made a few extremely astute observations about how the horses are looking or whatever, head to historic Wagner’s Pharmacy, a famous diner across the street from Churchill Downs, for breakfast – and to look for celebrities, who are often found here on Derby week.

  • A Note on Dress Code: One of the most fun parts of celebrating the Derby Season is dressing up! Traditional Derby Attire is fabulously over-the-top. We’re talking huge hats paired with floral or pastel cocktail dresses for ladies, and ridiculously patterned suits in bright colors (primarily pinks and greens) for gentlemen. It’s gaudy, it’s silly, and it’s the best time of year to break out your most fabulous outfit to fit right in! We’ve got a full guide to what to wear to the Derby, including a few budget-friendly suggestions, in our Kentucky Derby tips guide.
See also
Kentucky Derby Tips: The Ultimate First-Timer’s Derby Guide (by a local)

Visiting Churchill Downs during the rest of the year

If you’re visiting Churchill Downs outside of Derby season, you’ll want to check the events calendar. Although the museum is always open, horse races don’t run year-round, so if you’re interested to see an actual race you’ll need to make sure your dates line up with their schedule. Sunday races typically begin around 12:45 pm.

And while you don’t necessarily need to follow traditional Derby attire during the off-season, you certainly still can, and it is absolutely still appropriate. You won’t be the only one dressed up for a day at the races – it’s all part of the fun! I mean, when else can you wear a hat the size of a pizza pie or rock a lime green suit?!

If you’ll be heading to Churchill downs a little later in the day, pick one of our favorite brunch restaurants in Louisville – whichever one is closest to your accommodation. Then, spend your afternoon exploring the Derby Museum and watching the races.

Visit the Speed Art Museum

If you’re able to tear yourself away from the thrill of the track, Louisville’s premiere modern art museum is just up the street – and free to visit on Sundays!

Located adjacent to the University of Louisville’s campus in Old Louisville, the Speed Art Museum is the oldest, largest, and foremost museum of art in Kentucky.

Called one of “The World’s Most Beautiful New Museums” by Travel & Leisure Magazine (the building is rad, seriously… you should visit just for the selfie) the museum features rotating exhibitions on a diverse array of ancient, classical, and modern art.

Spend a few hours here feeling cultured and classy before heading back downtown for your last evening in Louisville.

Beer from Upland Brewery in Jeffersonville, Indiana with the Louisville skyline in the background across the Ohio River.
Upland Brewery in Jeffersonville, Indiana is only about a 10 minute walk from the end of the Big Four Bridge, and it has a stunning view of the downtown Louisville skyline.

Dinner at Upland Brewery in Jeffersonville, Indiana

The northern border of Louisville is defined by the deep, heavy Ohio River. Downtown, the Ohio River defines the waterfront, and just across the water is our northern neighbor, Indiana. Southern Indiana is so close that the greater Louisville area is known as “Kentuckiana.”

Indiana is so close that you can actually walk to it: the Big Four Bridge is a traffic-free pedestrian bridge connecting Waterfront Park in Louisville to downtown Jeffersonville, Indiana.

Despite our closeness, we do have a love-hate relationship with our northern neighbor which is almost as tense as the relationship between Louisville and Lexington. (Oh, by the way: try not to wear too much blue during your trip, or people might think you’re a UK fan.)

But as an Indiana University alumni and technical Hoosier (which makes me neutral in the KY/IN rivalry), I can tell you that there are many wonderful things in Indiana, and Upland Brewery is one of them. This brewery was founded in charming Bloomington, home of my alma matter and a liberal, artistic bastion in an otherwise red state – not unlike Louisville!

Plus, it’s only about a 10 minute walk from the end of the Big Four Bridge, and it has a stunning view of the downtown Louisville skyline.

Upland Brewery is one of the best breweries in Louisville & Southern Indiana, specializing in tart, sour beers that pair perfectly with a pimento and beer cheese pretzel starter (see, that’s super Kentucky), brewery fries, or the whipped feta and honey appetizer. Their menu features carefully curated, southern-inspired brewery fare like burgers and sandwiches, and they’ve got a few delicious vegetarian options, too!

Stroll over to Upland Brewery and enjoy a relaxed dinner before meandering back to Louisville around sunset.

  • Travel Tip: If you have to leave earlier in the day on Sunday to get back home, head to Upland Brewery for a late lunch instead, so you can say your goodbyes to Louisville with an incredible view of the skyline!
See also
The 26 Best Louisville Breweries (and Southern Indiana, too)

The Belle of Louisville returning home underneath a pink sunset on the Ohio River in Louisville, Kentucky.
Watching the sunset from the Big Four Bridge is the perfect way to say goodbye to Louisville!

Watch the sunset at Waterfront Park

Louisville has amazing sunsets. I think it’s because Louisville is located in the Ohio River Valley, which does all kinds of things to our weather and air quality – because truly, our sunsets are ridiculous. Like, they don’t have those kinds of sunsets elsewhere, I’ve checked!

The best place to appreciate our incredible sunsets is at Waterfront Park. Waterfront Park stretches along the bank of the Ohio River in front of Downtown Louisville, and it’s a beautiful place to stroll or bike along the water, with paths running all the way long the waterfront and down scenic River Road.

As you admire the sunset and stroll along the park and the bridge, keep an eye out for the Belle of Louisville in the water below. Our beloved historic steamboat – originally named Idlewild, which I love – was built in 1914. For many years, she chugged along the mighty banks of the Ohio transporting goods.

These days she mostly carries passengers on nightly sunset cruises. But once a year during Derby season, she has a chance to show what she’s made of! The Great Steamboat Race is an extremely thrilling, high-speed, action-packed race down the river – if you consider two very old boats chugging along at 7 miles per hour for 30 minutes action packed, anyway (I definitely do).

As you watch the last rays of the sun dissappear over the Louisville skyline, say your goodbyes to Louisville. We hope y’all will come back real soon!

Unless…

Bourbon Tasting at Woodford Reserve Distillery in Kentucky
If you can extend your Louisville weekend trip one extra day, the Kentucky Bourbon trail is a must-do activity!

More Ideas for your Louisville Weekend Trip

If you’ve got room to squeeze in a few extra days in Louisville, here are some more suggestions for your trip!

Spend a day on The Bourbon Trail

I know, this itinerary included a lot of bourbon tasting and visiting distilleries. But … would you believe me if I said that it’s STILL worth it to visit distilleries along the Bourbon Trail??

There’s something truly magical about taking a drive through the rolling hills of Kentucky past horses grazing on green fields to a beautiful, historic bourbon distillery. It’s totally unlike visiting a distillery in downtown (even if the bourbon is just as good)!

That said, it’s hard to fit multiple bourbon distilleries into a single day (much unlike the distilleries in Louisville) because they’re all pretty spread out. So, limit yourself to two: we strongly recommend Woodford Reserve and Maker’s Mark. In our opinion, they’ve got the most beautiful grounds and the best tour experiences!

  • Travel Tip: Book a tour with Louisville-based Mint Julep Tours who will take care of the planning (and most importantly, the driving) for you.
"Weird, Independent, & Proud" mural in the Highlands neighborhood of Louisville, Kentucky
The Highlands neighborhood is scenic, quirky, lush, historic, and home to many of Louisville’s best local businesses.

Explore the Highlands

The Highlands neighborhood is one of the oldest in Louisville, and has long been one of its most lively and beloved. The neighborhood is scenic, quirky, lush, historic, and home to many of Louisville’s best local businesses. Plus, it’s one of Louisville’s most walkable – and most central – neighborhoods! Spending a day exploring the Highlands is a great addition to any Louisville itinerary.

Here’s how to spend a day in the Highlands:

  • Brunch at GraleHaus: Coffee shop and boujie brunch cafe by morning, biergarten by night, GraleHaus is a unique Highlands business located inside a converted church and one of our favorite places to get brunch in Louisville! Menu highlights include the oyster mushroom crepe, duck hash, and ground lamb with grits. And don’t skip a cup of excellent coffee – the Sorghum Cortado and the Lucky Charms Latte are unlike anything you’ll find anywhere else.
  • Meet a famous ghost at Cave Hill Cemetery: Historic Cave Hill Cemetery is the most beautiful and largest cemetery in Louisville. Print out a free informative Cave Hill Cemetery map and pay your respects to some of Louisville’s most famous residents: you’ll find the graves of Colonel Sanders, Muhammad Ali, and Meriwether Lewis Clark Jr. among many other famous historical people.
  • Take a hike in Cherokee Park: This enourmous, beautiful urban park winds right through the Highland for 389 hilly and forested acres, and through it wind myriad walking paths, hiking trails, and biking routes. The park was designed by Frederick Law Olmsted, who not only designed New York City’s Central Park, but also the majority of Louisville’s park system. The primary path through the park is a paved 2.4 mile scenic loop that you can walk or drive (the secret is to keep turning left to stay in the park, and turn right to exit!). The main hiking trial is a second loop surrounding the scenic loop, so it’s easy to pop in and out of the trails and hike for as long as you like!
  • Browse quirky local shops: The Highlands has a reputation for being weird, quirky, and downright eclectic, and much of that is thanks to the shops and businesses that line the Bardstown, Baxter, and Barret corridors. Spend a few hours strolling along and popping into whatever weird shop suits your fancy. We listed out a few of our favorite local shops in our Highlands neighborhood guide.
  • Drink some (more) craft beer: There are two fantastic Louisville breweries in the Highlands. Try Bourbon Barrel Aged beers, excellent Saisons and dark stouts at Great Flood Brewing, or the Strawberry Rhubarb Ale, the Sour Ale with Mango & Pineapple, and a Bourbon-Barrel Aged Chestnut Brown Ale at Against the Grain.
  • Dinner at Jack Fry’s: An iconic Louisville institution, Jack Fry’s is one of Louisville’s oldest restaurants, and has been a Highlands staple since 1933. Jack Fry was a gambler who loved boxing and horses, and the restaurant is decked out in sports memorabilia from a bygone era alongside pictures of famous visitors to Louisville who have stopped to eat in this classic Louisville restaurant. Today, Chef McClain Brown serves up classic dishes with modern twists, including Lamb Chops, Beef Filet, and the best Shrimp and Grits we’ve ever had (and trust us, we’ve had many).
See also
The Highlands Neighborhood Guide: Where to Eat, Drink, Play and Stay

Are you excited for your Louisville weekend trip? What questions can we answer about visiting Louisville? Drop us a comment below!

Before you go, be sure to check out these other posts:


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Bourbon distilleries. Steamboats chugging along the Ohio River. Horse racing. Welcome to Derby City, aka Bourbon City! We've created the perfect Louisville weekend trip itinerary packed with the best things to do in Louisville.
 
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2 Comments on Louisville Weekend Trip: The Perfect 3-Day Itinerary

  1. A foodie tour would be amazing in Louisville so you can see 8-10 restaurants & bars on one night. Great itinerary!

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