Louisville’s 11 Best Winter Date Ideas


Even though there may be snow on the ground, there’s plenty to do indoors around the city! Plus, there are some pretty sweet outdoor winter activities in Kentuckiana that you can only treat your date to during the cooler season.

1. See the Holiday Lights While Ice Skating atA�4th Street Live!

Nearly every sappy romantic comedy has an ice-skating scene with snow falling and lights twinkling in the background. Be the star of your own rom-com by heading down to 4th Street to enjoy the holiday lights and the outdoor ice skating rink.Hold hands, laugh and fall down while some Celine Dion song plays in the background or something like that. It’s probably the most romantic thing you could do in the winter months.A�If the ice skating on its own weren’t enough on its own, 4th Street will be decked out with holiday lights set to music as part of the 40 Nights Of Lights spectacle, totally adding to the ambiance.


Not only is this date option totes romantic, it’s affordable. You’ll seem original AND thoughtful, without having to spend a fortune at some swanky restaurant. What more could you ask for? Get out there and make the most of the weather, you love birds.

2. Enjoy a Fireside Dinner at The Village Anchor

This village-centered European-style root meets Parisian bistro offers a classy yet cozy ambiance. It’s a beautiful restaurant with flagstone walkways, ornate chandeliers, and most importantly, a fireplace to cozy up next to while you dine.

village anchor fireplace

The menu offers Southern-inspired fare that is rich, flavorful and original. Creamy shrimp & grits, fried chicken served with house-made garlic mashed potatoes, an innovative take on the hot brown (“The Hotter Brown”) served with pulled roasted chicken and candied Anchor Bacon – the options are endless and difficult to choose just one. The Village Anchor really pulls out all of the stops with an impressive wine list, immaculate presentation of dishes, all while remaining welcoming without the stuffy air you may have come to expect from upscale date-night locations.

3. Have Dinner and a Show atA�The Bard’s Town

The Bard’s Town is a intimate, laid-back, restaurant/pub/theater experience. It’s a cozy place to escape the cold, right in the heart of the Highlands. Everything from the barbecue sauce to the sausage to the marinades are made in-house. The entertainment ranges from original theater works to that of twelve other theater companies, to stand-up comedy, to improv comedy, to live music and everything in between.

Bard's Town

The Bard’s Town is a unique and very authentic local, Highlands-style experience. Stop in to see an original play and experience the grassroots arts and theater scene like never before, all while enjoying your dinner.

4. Sip on Hot Coffee or Tea in A Cozy Bed & Breakfast atA�Gralehaus

This cozy bed and breakfast is brought to you by the creators of theA�Holy GraleA�(and happens to be right next door and shares its beautiful Gralegarten). Gralehaus offers what you’d expect from a coffeehouse: espresso, pour-over coffee, and their own creative signature drinks. In addition to delicious coffee, Gralehaus serves Kombucha tea on draft, shrub soda, and an original brunch menu. Dinner is now also available on the weekends.


The breakfast offerings are creative explosions of flavor – like the lamb sausage & grits or the biscuit & duck gravy. Gralehaus also offers unique espresso beverages and teas. Plus, mimosas. It’s the best of a coffee shop and brunch spot, all in one.

5. Visit Museum Row for $5 February

Hoosiers and Kentuckians have an even more inexpensive way to escape the dreary winter weather: with a photo ID proving residency in either state, admission to The Frazier History Museum, Kentucky Museum of Art and Craft, Louisville Slugger Museum & Factory, and The Muhammad Ali Center is $5 each. Of course, in every month other than February, admission is still under $15, so it’s not going to break the bank, either way.


The exhibitions at these museums may be surprising and unexpected. The Frazier History Museum may SOUND stuffy, but its exhibitions are often quirky and engaging. It once featured a “mythic creatures” exhibition and is currently featuring a “holidays around the world” exhibition, a multicultural exploration of, well, holidays around the world.

6. Enjoy the Free Entertainment ofA�Winter WednesdayA�at the Clifton Center

Summer brings us WFPK’s Waterfront Wednesday, but sadly, this time of year it becomes too cold to enjoy our majestic waterfront. So, the party moves inside in the Clifton Center for the winter. It’s the same Waterfront Wednesday you know and love, just not on the waterfront. And there’s actual seats. And heating. Doesn’t that sound nice?

clifton center

Winter Wednesday is every third Wednesday of the month. It’s warm, it’s cozy, it’s free entertainment. WFPK brings Louisville today’s best music over the airwaves everyday, come out once a month to enjoy it in real life.


7. Relax with a Hot Coffee and Enjoy Art and Literature atA�McQuixote Books & Coffee

McQuixote Books & Coffee is nestled inside of theA�Tim Faulkner Art Gallery. The Tim Faulkner Gallery is not your standard art gallery. It is a re-purposed factory and pioneer of the renaissance of the Portland area, presenting unique art in its maze of rooms and exhibitions. It’s also a 1,500 capacity concert venue, presents plays, features a resident circus troupe and is generally a cornerstone of the offbeat community.


This is the perfect place to spend a quiet, relaxing day with your beau. Grab a coffee to warm you up as you explore the ever-changing exhibitions of the gallery.

8. Experience Offbeat Entertainment atA�TheA�Alley Theater

The Alley Theater’s vision is to provide a theater experience that is enjoyable to all ages and walks of life. Here you may find audience-interactive performances as well as traditional sit-back-and-watch shows. It’s local, it’s arsty. The productions can be uproariously funny, intensely gripping and engaging, or some combination of everything in between.


It’s a theater by the people for the people. It’s unpredictable, progressive and informal theater experience, and it certainly doesn’t hurt that it’s affordable. Come check out their new location on Main Street.

9. Order a Wine Flight and Share Small Plates at Louvino

Louvino is a wine bar in the Highlands, which features several permanent wines and many rotating wines on their ever-changing wine list. There is always something new to try, and Louvino provides the full experience – the atmosphere is modern and sleek, yet welcoming and cozy, and their small plates are exquisite and exciting. Wine flights are Kentucky-themed, featuring an assortment of wines that represent the characteristics of the person the flights are named after.


A couple should expect to order 4 to 5 small plates to constitute a traditional-sized meal. Louvino’s plates are rich and savory, offering selections such as the Lamb Loin Chop with Truffle Mushroom Risotto, Demi-Glace or the Braised Short Rib Gruyere Mac and Cheese. You can’t go wrong with The Loaded Baked Potato Tots with Cheddar, Scallion and House Ranch or the Duck Fat Frites with White Truffle Aoli.

Louvino is truly an experience for the palate, from start to finish. Plus, you’ll impress your date with how in tune you are with the local culture – Louvino has only been open a few short months (all the while receiving rave reviews, of course).

10. Experience Contemporary Art atA�21c Museum Hotel

21c was founded by native Louisvillians with a vision to make contemporary art a daily part of people’s lives. It’s much more than just a place to spend the night – it’s an oasis of Southern hospitality coupled with artistic expression and culinary creativity. It features rotating exhibitions of living artists in its museum, which offers free admission to all – not only to guests.

21c has done its part to keep Louisville weird with its concept of a boutique hotel + art museum. While you’re there, you should definitely check out Proof On Main, the hotel’s restaurant. Their menu serves up nationally-renowned, Southern-inspired sophisticated fare and their cocktails are exquisite.

11. Dress Up For an Evening at Actor’s Theater

Louisville’s own Actor’s Theatre is an internationally-renowned epicenter of creativity. It is recognized locally as a leading arts organization in Louisville. Actor’s Theatre is dedicated to producing new plays and has been drawing theater-goers from all around the world for the last 40 years.

christmas carol 2

Although Actor’s is renowned for providing a venue for new works and talent, of course, classics are brought to the stage. Going out to see A Christmas Carol is a great way to get into the holiday spirit! Check out their calendarA�to stay up-to-date with what’s onstage.

Featured Image Credit: Cedric Santarromana