The Highlands Neighborhood Guide: Where to Eat, Drink, Play & Stay

The Highlands is one of the most iconic neighborhoods in Louisville, and for good reason: it has amazing food, a hip atmosphere, and is the perfect place to find out why “Keep Louisville Weird” is one of the city’s slogans! If you want to go barhopping, visit Cherokee Park, admire street art, or stroll along streets lined with eclectic shops, this is the spot.

Built around the vibrant Bardstown Road corridor, the walkable Highlands neighborhood is both historic and cool at the same time. In our Neighborhood Guide, you’ll learn all about the many things to do in the Highlands.

Check out a few of these other neighborhood posts:

• The NuLu Neighborhood Guide: Where to Eat, Drink, Play & Stay
• The Clifton & Crescent Hill Neighborhood Guide: Where to Eat, Drink, Play & Stay
• Old Louisville Neighborhood Guide: Where to Eat, Drink, Play & Stay
• Butchertown Neighborhood Guide: Where to Eat, Drink, Play & Stay

Introduction to the Highlands

Tree-lined streets. Colorful murals. Eclectic shops and local businesses. Delicious restaurants. Ornate Victorian homes. Beautiful parks. 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, historical, and home to many of Louisville’s best local businesses. Plus, it’s one of Louisville’s most walkable – and most central – neighborhoods!

The Highlands is not named for its many head shops, but rather because of its elevation. The area sits on a ridge between two forks of Beargrass Creek, above the flood plain of the Ohio River.

While the Highlands today is seen as the epicenter of all things cool and the place to grab amazing food, it was a challenge the develop thanks to the steep 60-foot climb to the top of the flood plain (which would come in handy later).

The Highlands is centered around a vibrant stretch of Bardstown Road, which lasts for three miles starting at Baxter Avenue and Broadway and ending around Trevillian Way and Taylorsville Road.

At the northernmost tip of the Highlands, both Baxter Avenue and Barret Avenue are also fast-growing areas full of local businesses and shops.

The Highlands is located about 2 miles south-east of downtown and the Ohio river. It’s a quick 10 minute drive, 15 minute TARC ride, or 20 minute bike ride from downtown. The Highlands is bordered by Phoenix Hill and NuLu to the north, Paristown and Germantown to the West, and Clifton to the East.

While the Highlands may sound like a single area of town, it actually encompasses nine separate neighborhoods all lumped under the “Highlands” label (11 if you count the “Upper Highlands” as well). All the neighborhoods of the Highlands branch off from Baxter or Bardstown Road – this thoroughfare is the main thread that ties the area together.

Most locals tend to call the entire area – or even smaller areas – by the moniker “The Highlands.” But because the Highlands is so large, it helps to know some of its micro-neighborhoods.

The “Original Highlands” is an area between Baxter Avenue and Barrett Avenue at the start of Bardstown Road. This is the oldest section of the Highlands, developed starting in 1814. The area was once served by a 24-hour streetcar, whose tracks still lie underneath beautiful Highland Avenue. Today you can still see plenty of original Victorian houses and working-class shotgun houses in this micro-neighborhood, most of which are in the Queen Anne style.

Cherokee Triangle is a historic preservation district of the Highlands, full of lavish mansions (both modern and brick Victorian) and luxurious, historic apartment complexes. This large area borders Cave Hill Cemetery and Olmsted-designed Cherokee Park. Looking at the neighborhood on a map, it really does make a triangle shape!

Another popular area of The Highlands is farther south, down by Douglass Loop. This area includes the Douglass Loop farmer’s market every Saturday, as well as coffee shops and eccentric stores.

The Story of The Highlands

Development in The Highlands began as early as 1814 in the Original Highlands area, but it would take about a century to fully develop.

Bardstown Road was originally the Bardstown Turnpike, which began construction in 1819, where you would pay a toll to take the new 55-mile road towards Bardstown, Kentucky.

It was along this area that the Original Highlands attracted German immigrant farmers who called the area “New Hamburg”. With the building of a high-tech, 24-hour horse-drawn streetcar line running along Highland Avenue in 1871 – part of Louisville’s once-extensive streetcar system.

In the late 1800’s and early 1900’s,  Frederick Law Olmsted designed and developed two beautiful parks in the Highlands: the smaller, residential Tyler Park, and the sprawling, stunning Cherokee Park – the Highland’s crown jewel!

By this time, the area had earned its reputation as a vibrant place to live and visit. By the 1930s, the area had been developed into what we call the Highlands today.

Thanks to the elevation that gives the area its name, much of the neighborhood has been spared by the floods that plague Louisville. During the Great Flood of 1937, which devastated 75% of the city, they had to build a bridge to get to the Highlands!

As a result, much of the history of the area has been well-maintained and preserved. You can still see plenty of original brick Victorian houses and working-class shotgun houses in the Original Highlands neighborhood, as well as the original Victorian brick homes in the preservation district of Cherokee Triangle.

Things to do in The Highlands

As the Highlands is the cultural hub of Louisville, there is no shortage of excellent places to explore, fabulous places to eat, and amazing things to do! You could spend a few hours or days in the Highlands and never get bored. Below are the places we recommend you definitely check out.

Activities in The Highlands

The Highlands is home to the vibrant Bardstown Road corridor, which is lined with shops, restaurants, coffee shops and business – most of which are locally owned! Strolling up and down along Bardstown Road is an activity in and of itself, and comprised roughly 90% of what I spent my time in high school doing.

But that’s not all: there are also tons of local businesses along Baxter Avenue and Barret Avenue, offering plenty of local gem to explore in the Highlands!

Take a Food & history Tour

The walking food tour of the historic Highlands neighborhood by Louisville Food Tours explores the history and gorgeous architecture in the Original Highlands and Cherokee Triangle neighborhoods, while tasting delicious dishes from local restaurants .

The Original Highlands the oldest section of the Highlands neighborhood, and Cherokee Triangle is its most beautiful. Historic Victorian homes branch off of the Bardstown road thoroughfare on lush streets lined with huge trees.

As you walk along some of Louisville’s oldest and most iconic streets, you’ll taste (and drink) local specialties like biscuits & gravy, beer cheese, and bourbon balls; visit the final resting place of Muhammad Ali and Colonel Sanders; and admire beautiful Victorian homes in the Original Highlands and Cherokee Triangle neighborhood while learning about different styles of architecture from Louisville’s opulent heyday.

You can book your tour at Louisville Food Tours and use the code LGL10 for 10% off.

Search for Street Art

The Highlands is home to a ton of street art! You’ll find murals decorating brick walls, businesses, and even utility boxes all over the neighborhood.

This guide on My Colorful Wanderings will help you find them all, plus many of the other great murals in town!

Browse 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 business corridors.

Spend a few hours strolling along and popping into whatever weird shop suits your fancy. A few of our favorite local shops are:

• Unorthodox Shop: Oddities, curiosities, antiques, and art. Like what, you ask? Oh, you know … rattlesnake vertebrae earrings, skulls, taxidermy, witchy/occult stuff, that sort of thing. It’s all wonderfully unorthodox!
• Goldheart Stones: Stones, gems, crystals, rocks – you’ll find them all here, and more.
• Fat Rabbit Thrift: Secondhand clothing, records and other outdated media tech, knick knacks, “curiosities,” whatever this is, and a whole bunch of other hard-to-describe and delightfully strange stuff.
• Electric Ladyland: a 70’s-themed hippie record shop and headshop known for it’s eclectic assortment of oddities. This shop is like taking a time machine back to the 70s. It’s groovy AF!
• Natural Mystic: Need some crystals, incense, witchcraft supplies, esoteric ephemera, Metaphysical items, or tie-dyed stuff? Natural Mystic has all of it and more. (One thing they don’t have is a website)
• Hey Tiger: Handmade and vintage gifts and goodies! There is so much packed into this little store, it’s pretty much impossible not to find something to take home with you.
• Dot Fox: Dot Fox has been filled with clothing, jewelry, and accessories that are too way cool for me to pull off since I was in high school, and I’m still not cool enough. Come browse all the extremely cool things, or get a cup of coffee at the teeny coffee shop inside!
• Baz and Bea: This cute little boutique sells clothing and accessories primarily made in the USA and partners with other organizations that offer ethically made & sustainable products.
• Carmichael’s Bookstore: The quintessential local bookstore. Browse carefully curated books and selections, including local authors, and then head across the street to Heine Bros to enjoy your new book over a cup of coffee!
• UltraPop Shop: Like pop art and pop culture? How about a whole store bursting with it? UltraPop sells collectible toys, art & design books, local art, and a whole lot more.
• Dirty Tease: Want a local Louisville t-shirt, a silly graphic tee, or a Black Lives Matter shirt? This LGBTQ-owned custom print shop sells it all – and more. Browsing the walls of creatively designed shirts will make you giggle, and it’s hard to leave empty-handed.

Visit the Kizito Cookie Factory

For every kind of cookie, head to the Kizito Cookie Factory, which is an experience in itself. Elizabeth Kizito started making cookies when she moved here from Uganda in 1975, and locals all recognize her at events walking around with a huge basket of cookies on her head!

The Kizito Cookie Factory also sells folk art from Uganda that her family ships to her. She says that her secret ingredient is “my family’s love and perseverance; the beauty and magic of Africa; the American Dream; are all mixed in next to the chocolate chips and butter and nuts.”

My favorite flavors are Gettin’ Lucky in Kentucky, Snickerdoodle, and Pumpkin Chocolate Chip.

• Kizito Cookie Factory | Address: 1398 Bardstown Road, Louisville, KY

Snuggle a kitten at the Purrfect Day Cafe

The Purrfect Day Cafe is the purrfect way (hehe) to grab a good cup of coffee (or wine or beer) and a treat and play with a kitten! Or you know, do yoga but with cats.

Their main room has all adoptable 2-4 month-old kittens from June to December, while their loft has adult cats you can visit and adopt. It’s clean, responsible, and a relaxing way to help socialize some little kittens as they find their forever home. They even have kitten yoga if you wanna get some stretches in with the kittens (just don’t call it downward dog!).

Of course, you can just come and play with a kitten without adopting, but the temptation may be just too much! From January to May, the main room features 6-month-old to 5-year-old cats that are just as adorable!

Places to Eat in The Highlands

The Highlands area is home to one of the most diverse food scenes in Louisville: you have southern fried cooking mingling with Cuban food and vegan restaurants! Many of Louisville’s best places to eat are located in the Highlands – so many that there’s even a Highlands food tour by Louisville Food Tours!

Below are a few of our favorites – and although the list is long, we actually really struggled to edit ourselves down!

Jack Fry’s

Jack Fry’s is one of Louisville’s oldest restaurants, and has been a Highlands staple since 1933 when it was opened by a man (named, unsurprisingly, Jack Fry).

Jack Fry was a gambler who loved boxing and horses. As a result, Jack Fry’s was decked out in sports pictures from a bygone era that still hang there today – 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).

• Jack Fry’s | Address: 1007 Bardstown Road, Louisville, KY (The Highlands)

The Fat Lamb

The Fat Lamb serves up “creative, upscale comfort food.” Their chef Dallas McGarity, won an episode of Chopped, where contestants have to turn mystery items into a three-course meal.

Try the chili & turmeric roasted cauliflower as an appetizer, which has a savory and smoky flavor from the paprika and pockets of gooey feta. We also love the ricotta gnocchi & lamb ragu with housemade ricotta dumplings and slow-cooked lamb. For a veggie option, try the cumin black bean falafel with truffle fries for a twist on a classic middle eastern dish.

Oh, and if you’re a bourbon snob (or just wish you were), they also have Pappy Van Winkle on the menu!

• The Fat Lamb | Address: 2011 Grinstead Drive

Noche Mexican BBQ

As you enter the main dining area, your eyes are immediately drawn to a stunning mural of a woman adorned in full calavera makeup overlooking the restaurant amisdt high arched rafters. She is illuminated by a rainbow of colorful stained glass – remnants from the church that this building once was.

All around the restaurant are nods to Dia de los Muertos, like colorful papel picado flags and adorned ofrendas. Amidst this dramatic interior is served some of the best Mexican food and drinks in town, all carefully crafted with a Southern twist. This is one of those rare restaurants that serves up both incredible food and a phenomenal ambiance! To get the most bang for your buck, plan to visit on Taco Tuesday, when the pricey menu offers a selection of cheaper options.

Ramsis’s Cafe on the World

Ramsis’s Cafe on the World pretty much perfectly sums up the Highlands: eclectic, exotic, and totally diverse.

In this restaurant filled with treasures from the owner’s travels, you can have bangin’ dishes like the vegan Egyptian Kitchen with ditalini, lentils, chickpeas, toasted angel hair, Basmati rice, fried onions and a fiery harissa on the side, or Ribs of the Caribbean with smoked pork ribs, mango BBQ sauce and grilled Z-potatoes.

• Ramsis’s Cafe on the World | Address: 1293 Bardstown Road

Dragon King’s Daughter

Dragon King’s Daughter (known as DKD) is THE place for sushi in the Highlands. Their sushi list is extensive, with lip-smacking rolls like the Black Widow Roll with deep-fried soft shell crab, spicy mayo, & green onion inside and diced red tuna, jalapeño, & hot sauce outside, and the Hoosier Momma with escolar & avocado inside, toro salmon & scallop outside, and torched & drizzled with chili oil.

DKD also offers an extensive beer list stocked with local beers like BBC’s Nut Brown Ale as well as sake. Stop by for happy hour from 3-6pm every day which means you can sample booze and rolls for a fraction of the cost.

• Dragon King’s Daughter | Address: 1126 Bardstown Road

Taco City Louisville

Taco City Louisville in the Highlands neighborhood is legit, y’all. Ever since Lia’s Mexican, California-born & raised husband saw Buffalo Chicken as a meat option for a burrito in Chicago, he’s been suspect about Mexican food in the Midwest.

But Taco City Louisville is delicious – and not the typical tex-mex style that you’ll find in the rest of Louisville (though we do, surprisingly, have a wide variety of excellent tacos in town – check out our guide to the best tacos in Louisville).

We highly recommend the mole braised chicken tacos, whose sauce is a touch spicier than mole usually is but every bit as aromatic and rich, as well as the super savory tinga tacos.

• Taco City Louisville | Address: 1283 Bardstown Rd

Homemade Ice Cream & Pie Kitchen

A Louisville institution, you’ll find Homemade Ice Cream & Pie Kitchen on the southern end of The Highlands around Douglass Loop serving up exactly what they claim: delicious homemade ice cream… and fantastic pie!

We recommend picking up a slice of Kentucky Butter Pie or Chocolate Chess Pie. And if you visit during Derby Season, you’ll find Chocolate Pecan Horse Racing Themed Pie (or whatever they’re calling it that definitely isn’t Derby Pie(tm), wink wink). Their version is made with pecans and the original is made with walnuts, but you know what? They’re both delicious.

If you haven’t tried a chocolate nut horse racing themed pie, you absolutely must try this classic Louisville dessert – it’s one of the most famous Louisville foods! Just … don’t ask for it by name. Because someone might get sued.

• Homemade Ice Cream & Pie Kitchen | Address: 2525 Bardstown Road

Wiltshire Bakery and Cafe

Craving a buttery, flaky croissant or just need a delicious, quick grab-and-go lunch? Wiltshire Bakery has long been serving up some of the best bakery and cafe staples in town!

Head there for breakfast to grab a delicious latte and French Toast made with croissants topped with meyer lemon-pomegranate marmalade. For lunch, you’ll find upscale twists on lunchtime classics like potato leek soup, sourdough toast, seasonal salads, and fresh-baked bread and pastries. Pretty much everything is good here, and you can’t go wrong!

• Wiltshire Bakery and Cafe | Address: 901 Barret Ave

GraleHaus

Coffee shop and boujie brunch cafe by morning, biergarten by night, GraleHaus is a unique Highlands business located inside a converted church.

We recommend visiting for brunch – Gralehaus is one of our favorite places to get brunch in Louisville! Highlights include the oyster mushroom crepe, duck hash, and ground lamb with grits. Or just stop by for a truly excellent coffee – the Sorghum Cortado and the Lucky Charms Latte are unlike anything you’ll find anywhere else.

• GraleHaus: Address: 1001 Baxter Avenue

Havana Rumba & Tapas Bar

Craving Cuban food? Havana Rumba is a phenomenal Louisville staple restaurant! We recommend ordering the crispy Masas de Puerco or the classic Ropa Viejo, both served with rice, beans, and sweet plaintans.

Havana Rumba also serves up delicious Cuban twists on Spanish-style Tapas, including classics like Croquetas and Patatas Bravas – except made with Yuca!

And definitely also get a Mojito – they’re served with a stick of fresh sugarcane (and 50% off on Wednesday nights)! Oh, and save room for Tres Leches for dessert!

• Havana Rumba | Address: 2210 Bardstown Road

Georgia’s Sweet Potato Pie Company

Georgia’s is known for their sweet and creamy sweet potato pie with a flakey crust. Try a bite-sized pie in the original Southern classic, or an upgraded version like a Bourbon Pecan Sweet Potato Pie, one of the best desserts in Louisville.

Best of all is the mission behind the business: the sweet potato products allow the bakery to offer free children’s books about love, diversity, and acceptance through their Pies with Purpose project. By eating delicious sweet treats, you’ll also be supporting the local Louisville community.

• Georgia’s Sweet Potato Pie Company | Address: 1559 Bardstown Rd, Louisville, KY

Coffee Shops in the Highlands

There are so many excellent coffee shops in Louisville, and the Highlands has a handful of them! Here’s where to get your morning pick-me-up.

Quills Coffee

With several locations throughout Louisville, including one on Baxter Avenue a block away from the start of Bardstown Road, Quills Coffee is our favorite third wave/specialty coffee shop in Louisville (and we’re huge coffee snobs).

Head to Quills for pour-overs and single-origin beans. Feel free to strike up a chat with your barista about the notes in your single-origin pour-over or espresso: they’re passionate and knowledgeable about coffee, and it shows!

• Quills Coffee | Address: 930 Baxter Avenue

Heine Bros Coffee

Heine Bros Coffee is the self-proclaimed “original Louisville coffee house,” and they’re about as Louisville as you can get. Their coffee is all organic and fair trade, but this is a 2nd wave coffee shop, which means it’s a great place to get a delicious, sweet coffee drink and then spend a few hours relaxing, reading LEO and saying hello to everyone you went to high school with.

Look, I’m not gonna lie to you: I hate Starbucks, but I love Heine Bros Coffee.

Try a Vint Julep, made with whiskey-infused sugar and fresh mint, or one of their delicious, creamy blended Icebergs, which are so much better than Frappuccinos.

If you’re looking for something with whipped cream and syrup and blended to perfection, you need to go to Heine Bros Coffee. Oh, and their chai is amazing, too!

• Heine Bros Coffee | Address:  1250 Bardstown Road or 2200 Bardstown Road

Sunergos Coffee

Sunergos Coffee is a third wave coffee shop that roasts their own beans and makes a damn fine espresso. You’ll find sustainably sourced single origin beans alongside seasonal blends, all with delicious tasting notes – coffee snob approved.

The Highlands location of Sunergos is tucked away in the Deer Park micro-neighborhood, across the street from Highland Middle School.

• Sunergos | Address: There are several locations in Louisville. Find one near you!

Safai Coffee

Safai Coffee roasts their own organic, specialty coffee beans in micro-lots, and for fans of medium and dark roasts, the drinks will hit the spot! Pair your coffee with a delicious sweet or savory crepe.

• Safai Coffee Shop | Address: 1707 Bardstown Rd

Breweries in the Highlands

A few of the best Louisville breweries are located in the Highlands:

Great Flood Brewing

Tucked unobtrusively into a space on Bardstown Road in the Highlands neighborhood, Great Flood Brewing is much larger inside than it first appears from the outside.

The taps at this Louisville brewery offer everything from Bourbon Barrel Aged beer to excellent Saisons and dark stouts. In addition to their own brews, Great Flood serves up a few notable outside offerings, such as the delicious Beer X-Tacy (a play on a much-beloved, but now closed, local Highlands record store called Ear X-Tacy, RIP).

• Great Flood Brewing | Address: 2120 Bardstown Road, Louisville, KY

Against the Grain Public House

Louisville’s first brewer owned and operated brewpub. Try any of their Bourbon-Barrel Aged Imperial Stouts – there are several varieties! We also dig the Strawberry Rhubarb Ale, the Sour Ale with Mango & Pineapple, and a Bourbon-Barrel Aged Chestnut Brown Ale.

Against the Grain has a fantastic food menu, too.

• Against the Grain | Address: 1576 Bardstown Rd

Parks in The Highlands

One of the best parts of The Highlands is that it’s home to Chrokee Park and Cave Hill Cemetery, two of the beloved green spaces in city. Going to these places are activities in themselves, and you could easily spend several hours in each.

Cherokee Park

Cherokee Park is a big, beautiful park in Louisville winding through the Highlands. It’s hilly and forested over 389 acres, and through it wind myriad walking paths, hiking trails, biking routes, and even a 2.4 mile scenic loop that you can walk or drive car if you’re the kind of person who doesn’t get lost easily and is able to follow signs (this disqualifies me– though I hear the secret is to keep turning left to stay in the park, and turn right to exit!).

The park was designed by Frederick Law Olmsted, who not only designed New York City’s Central Park, but also Louisville’s other major parks, Iroquois and Shawnee, as well as the city’s four parkways. Olmstead believed in the healing power of nature and its ability to refresh the soul, and probably the best way to do that is to get off the scenic loop and check out some of the hiking trails surrounding the park – this is one of our favorite places to go hiking in Louisville.

The main trail is like a second loop surrounding the scenic loop, so it’s easy to pop in and out of the trails where you like. Taking the trails means you get to discover hilly forests, boardwalks over swampy areas, and even a bird sanctuary!

If you’re feeling more social, check out Dog Hill where you can always find dogs and their owner’s gathering, or Hogan’s Fountain where there’s a fountain from 1905 featuring a statue of the Greek God Pan, a large gazebo (the Witch’s Hat), a basketball court, and a play place! So go for a drive, a stroll, or even a hike or trail run, you Olympic athlete, you!

• Cherokee Park  | 745 Cochran Hill Rd. Louisville, KY

Cave Hill Cemetery

Historic Cave Hill Cemetery is the most beautiful and largest cemetery in Louisville. Stroll through its quiet, garden-adorned grounds past ponds and mausoleums and think about the nature of life, the universe, and everything.  

You can 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.

Cave Hill is also an arboretum, so you can take in all different kinds of trees as you stroll past lakes with gently gliding swans, ornate tombs, even a giant sphinx gravestone. And since the cemetery began in 1846, you can expect to find some very ornate and interesting resting places. It really is a relaxing place to wander around for a couple of hours!

• Cave Hill Cemetery | 701 Baxter Avenue, Louisville, KY

Tyler Park

Tyler Park is located off of Baxter Avenue, and is like the little sister of Cherokee at only 13-acres. The park originally opened in 1910, and since then has undergone some major restorations to give it a modern playground, a sprayground (basically a glorious fountain to run through in the summer when it’s hot), tennis courts, and a shelter to picnic in.

This is a great place for an afternoon stroll, especially under the historic bridge. In the winter, Tyler Park has a great sledding hill!

• Tyler Park | 1501 Castlewood Avenue, Louisville, KY

Nightlife in The Highlands

The Highlands is the best spot in Louisville for nightlife. Hands down. Anyone who tells you it’s Fourth Street Live is not a resident- The Highlands has the unique, weird, and local joints where you can hit the best bars, breweries theatres, and all the best of Louisville after dark. You can even check out a Highlands bar crawl like this one.

Neat Bourbon Bar & Bottle Shop

When it comes to bourbon bars in Louisville, Kentucky, Neat is one of the neatest best. The interior is both cozy and elegant, with dark wood walls fanning out from a polished bar lined with comfortable leather stools in front of a truly impressive display of bourbons. Sidle up to the bar and order a Looavul, cocktail made with bourbon, pecan liqueur, mezcal, and black walnut bitters.

But Neat is more than just a really neat great bourbon bar – it’s also a bottle shop featuring rare, hard-to-find bourbons. For Bourbon People (y’all know who I mean when I say that, right?), Neat is basically Disneyland. Locked up behind glass like a carefully curated museum, you’ll find pretty much everything here that you can’t find anywhere else – but expect to pay a pretty penny for it: there are bourbons here that cost $13k a bottle. And to think, I used to buy bottles of Blanton’s just because I liked the horse topper on the bottle…

• Neat Bourbon Bar & Bottle Shop | Address: 1139 Bardstown Road Louisville, KY

O’Sheas Irish Pub

The Highlands is home to the best Irish bars in Louisville, all conveniently clustered together. There are 3 Irish bars right next to each other, and everyone has a different opinion about which one is “best,” but our favorite is O’Sheas.

• O’Shea’s Irish Pub | Address: 956 Baxter Ave

Highlands Taproom

If you like live music, be sure to stop by the Highlands Taproom and see who’s playing. The Highlands Taproom is actually two full bars housed side by side, with over 25 beers on tap, a full kitchen, and karaoke and trivia nights!

Out side a large patio connects the two bars, strung with rainbow lights that glitter in the night. It’s got a funky, local, and a devil-may-care kind of vibe, with cheap drinks and good company. All you need!

• Highlands Taproom | Address: 1058 Bardstown Road

The Caravan Comedy Club

Need a good laugh? The Comedy Caravan hosts plenty of touring comedians as well as live music. And if you want to try your hand at becoming the next comedic superstar, they also host an open mic night. So write your best jokes, or let the professionals take care of it, and head down to the Caravan Comedy Club!

• The Caravan Comedy Club | Address: 1250 Bardstown Road

Chill Bar Highlands

True to its name, this gay bar is super chill. But there’s always something going on, from DJs spinning on the patio, to trivia nights, showtunes sing-alongs, Drag Race watch-a-longs & other fun events.

Psst: if you are not a member of the LGBTQ+ community, be aware that you are entering a queer space and need to be mindful of both your behavior and your mindset – this guide will help!

• Chill Bar Highlands | Address: 1117 Bardstown Rd Louisville, KY

Where to Stay in The Highlands

Your best bet for the Highlands is to stay in a vacation rental! There aren’t many big hotels here, but there are some incredibly cute, centrally located apartments and lofts.

• This stylish Highlands Home is the perfect “walk to all” location. Its bright and artsy, with four bedrooms, a modern kitchen, and a beautiful outdoor deck area. The location truly is perfect too- by the intersection of Bardstown and Eastern Parkway, you’ll truly be able to walk to the best of the Highlands, including Cherokee Park.
• Located in the Baxter Avenue section of the Original Highlands, this Southern, Chic Home off Barrett Avenue is a stone’s throw away from both the historic Cherokee Triangle and NuLu. This home is spacious and hip, with a fantastic bathroom (and a luxurious soaking tub and marble shower!) and a secluded outdoor patio with a huge hot tub!
• This Five Bedroom House is perfect for groups as it has 5(!!) bedrooms and is nestled in the Cherokee Triangle area near some of the best Highlands nightlife. You’ll be able to eat, and drink, and walk to all kinds of things from this location!

Map of Things to Do in the Highlands

Wish you had a map with all of the stuff in this post? Well, wish granted: we made ya one! Bookmark this page to come back to next time you’re exploring the Highlands.

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Are you excited to explore more of the Highlands? What questions about this neighborhood can we answer? Drop us a comment below!

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

• The 63 Best Things to Do in Louisville, Kentucky
• 9 Distilleries in Louisville, Kentucky: from Bourbon to Brandy
• The NuLu Neighborhood Guide: Where to Eat, Drink, Play & Stay