Kentucky Derby Style: Where to Eat, Drink, Shop + More in Louisville * Part II – Clifton, Frankfort Ave, St. Matthews & The Highlands

In the quest to keep you informed on all things Kentucky Derby and ready for the first Saturday in May, I’m back with Part II of my Where to Eat, Drink, Shop and more post. Part I seemed to go over really well so I’m excited to expand on it today and move a little outside of the downtown area.

Like I said in Part I, this is certainly not a comprehensive list. It’s just a mix of my favorites that will be ready for you when you come to town. There’s a ton of amazing restaurants that also aren’t on the lists, mostly because they are often booked up months in advance so I wouldn’t want to recommend somewhere you wouldn’t be able to go. After writing this one, I realize we MAY need a Part III for Germantown and the East End. Should we keep it going?

Next up after this is going to be a Derby FAQ so if you have any questions, make sure to let me know! 

Clifton/Crescent Hill 

Of all the areas in town, this may be my favorite. I’m probably a little partial since we used to live over here but I think it’s one of the most walkable areas in town. These are just a few of MANY options. You could grab drinks at more than a dozens spots along Frankfort Avenue plus there are shops, coffee spots, record stores, gyms and really whatever you need. On your trip to town, when in doubt go to Frankfort Avenue.

Grab a drink at… Before Dinner at Porcini

Dare I say, Porcini may be my favorite bar in Louisville. Mostly because at my core I’m a 65-year-old woman and also because I love sitting at the bar, ordering apps and enjoying my favorite dish in the entire city – their grilled romaine salad. At Derby time though, it is even more hopping. If you’re looking for a hipster/Instagram-worthy spot, this is not the place.

If you want to bump into locals and track-regulars though, this is it. Hang at the bar long enough and you’re bound to get some good wagering tips. You’re also likely to chat with some true characters while sipping on a great cocktail or cabernet.

Grab a drink at… After Dinner at The Silver Dollar

For a younger vibe and those ‘gram worthy pics, stop into The Silver Dollar after dinner. Or just eat there and keep the party going at the bar. With enough whiskey by the drink options to keep even the most discerning bourbon drinker busy for hours and the perfect patio, it’s a great spot to get a feel for the local scene.

It’s also a very solid brunch choice. Head over to The Kentucky Gent’s Instagram to see all the swoon-worthy brunch pics.

Grab breakfast at … Con Huevos 

Breakfast at Con Huevos is so good, they recently expanded the Frankfort Avenue location to accommodate even more breakfast taco lovers. You can’t go wrong with any of their breakfast options but my personal favorite is the Chiaquiles Con Huevos. That and their Cuban Iced Coffee are the perfect combination.

Oh and if there’s a wait, wander next door to Please & Thank You for a cup of coffee and a couple chocolate chip cookies.

Last minute outfit change… Him Gentleman’s Boutique 

This one is for the fellas …. who inevitably forget to pack their tie or the right shoes or socks. You may walk in for an appropriately festive accessory and walk out with a whole new outfit. Personally, I think they carry some of the most fun blazers – in prints, plaids and patterns – to up your look beyond a simple suit.

There’s no better time for the guys to go all out. So if you can’t find anything where you live, give the guys at Him a call and they can probably pull something for your day at the races.

For morning doughnuts… Bussman’s Bakery

You need donuts, Bussman’s has some of the best ones in town. End of story.

It also hasn’t changed in probably 40+ years so it’s a nice dose of nostalgia too.

Ann Taylor Navy Lace Shift Dress c/o
DKNY Mules | Headcandi Fascintor
Vintage Gucci Bamboo Bag

St.Matthews 
Grab a drink at… Before Dinner at Saint’s

With a Grade A patio and the most delicious cheese sticks, Saints is a laid-back, super lowkey spot to grab a beer after the track or when you roll into town. A true local sports bar, you’re not going to find anything crazy or super special here but that’s part of the charm.

It’s right in the middle of St. Matthews and is a gathering spot of people of all ages. From post-grab to your parents and everything in between. It’s a good place to go if you’re meeting people, need space and want to hang outside.

Catch live music at… Gerstle’s and/or Tin Roof

If loving cover bands is wrong, I don’t want to be right. My all-time favorites, yacht rockers Tony and the Tan Lines, normally do a Derby show at one of these spots but I couldn’t find out on their website/social whether they are playing. Either way though, Tin Roof and Gerstle’s are your spots for live music in the area. They’re just down the street from one another so you can bar hop from one to the other.

Just as an FYI – prepare for it to be crowded and a bit of a s**t show. That’s pretty much the story of Derby but I wanted to give you fair warning.

Last minute mani/pedi… The Nail Box.

I couldn’t possibly write a post about favorites without including my go-to nail spot. I absolutely love The Nail Box especially because they are so accommodating.

Need to knock out a mani/pedi in one hour flat, they’ve got you. Just make sure they know any time limitations in advance. They do gel, dip and regular mani/pedis as well as brow and body waxing so you can get a pedi and a brow wax in one spot. Make sure to meet the owner Tee, she’s the best.

Book a blowout at… Primp Style Lounge 

It may be tough to score an appointment but it’s worth putting them on the list because they may be able to squeeze you in or add you to the waitlist in case of cancellation.

The team at Primp are some of the best in town and do a good job of listening to specifically what you want. Similar to the Drybar experience, you pick from a style menu but can also bring in your own inspiration – which I definitely recommend. And Shannon, the owner, is one of the most stylish ladies in town and has a lot of great Derby inspiration herself. Make sure to follow her for lots of gorgeous looks.

The Highlands 

Admittedly, it’s been a while since I lived in the Highlands – so I’m not the best person to ask about all the best spots to go. Also, the Highlands is a big area spanning Bardstown Rd and Baxter Avenue. While the majority of the Highlands is super walkable, some of these spots can be pretty far apart depending on where you start.

Grab a drink at…Jack Fry’s

You’ll have a VERY hard time getting a table (we book a table for Tuesday Derby week like three months in advance) but you can have a drink at the bar. Jack Fry’s is a Louisville staple and is full of energy and excitement Derby Week.

When you walk in, you’re surrounded by Louisville history. Black and white images crowd the walls from floor-to-ceiling. You could easily get a brief history of the city just by browsing through them all. But that’s just the beginning. The cocktails are incredible, the wine list is on point and if you can score a spot at the bar to eat, the food is incredible. There’s really no going wrong but the pork chop is one of the best dishes in town.

Grab a burger and a beer at … Holy Grale

Housed inside a former Unitarian church built in 1905, Holy Grale is a gem tucked into the intersection of Baxter and Bardstown Rd. Known for their ever-changing selection of beers and their killer burgers, it’s a great place to grab a vacation lunch aka the kind with drinks.

Last minute mani/pedi… American Nails 

My girl Caitlin is a big fan of American Nails and that’s all I need to vouch for it. They have tons of chairs and walls of colors, so you can’t go wrong.

Grab a cup of coffee… Quills (Lower Highlands) or Heine Brothers (Upper Highlands)

Depending on where you’re staying, either of these local favorites will serve you a good cup of coffee with standard Louisville hospitality.

Get the best greasy spoon breakfast… Twig & Leaf 

Get there early so you don’t have to wait. A true greasy spoon dinner, Twig & Leaf is a Louisville icon.

They serve breakfast all day – get the pancakes – and stays open late. Some things never change and that’s why I love Twig & Leaf. It’s not some new spot trying to look like a vintage dinner. It’s just an old-school diner with a waitress who will lovingly call you ‘Honey’ while keeping your coffee hot. What’s not to love?

1 Comment

  1. Reply

    Jessica Able

    April 24, 2019

    Loved these part 1 and part 2. And, yes you gotta do Germantown – Germantown gal here!!
    I’d also love to see a post where you break down different areas of the track (ie the balcony off the Stakes Room is great for the iconic Twin Spires pic or what row is under cover in the Clubhouse.) Love tidbits like that when I’m trying to figure out where/what to check out at the track.

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