Lexington has been home for almost a decade. What began as a stop on my journey became the canvas where my creativity found a deeper meaning. As an award-winning visual artist and content creator, I’ve photographed cities around the world but Lexington? It continues to surprise me.
This guide isn’t about where to check in. It’s about what stays with you, what lingers after the picture is taken, after the night has ended, after the walk back to your car. Here are 8 places in Lexington that don’t just look good, they feel like something.
1. Downtown Dusk – The Soul of the City
📍 Short Street & Upper Street
If you want to understand Lexington, start here right where the street lamps flicker to life, casting warm shadows over historic bricks and glass towers. I took this shot just after golden hour, when the air starts to cool and the energy in the city sharpens.
What I love about this part of downtown is how much of Lexington’s personality is on full display. Old buildings still wear their original bones proudly, while new structures stand tall with intention. People are out grabbing coffee, walking dogs, heading to a show. It’s alive, but not chaotic.
📸 Pro Tip: Walk from Third Street to the Fifth Third Pavilion. The architecture, reflections, and storefronts along the way are pure visual candy.
2. Old Frankfort Pike – Bluegrass Elegance
📍 A Scenic Stretch Outside the City
This view always stops me. Maybe it’s the symmetry of the fences. Maybe it’s the quiet authority of the horses. Or maybe it’s just that Lexington doesn’t try to sell you an image, it just is. I pulled over one morning with my camera because the fog was just lifting, and the light was like something out of a movie.
This is Lexington’s countryside: open skies, heritage farms, and the kind of stillness you don’t find in cities. But make no mistake, there’s elegance in the dirt. Wealth, culture, and deep-rooted traditions live here. You don’t have to be a horse person to feel it.
📸 Pro Tip: Time your visit around sunrise or just before sunset. The light rolls across the land in waves, and the photos frame themselves.
3. 21c Museum Hotel – Art That Belongs
📍 167 W Main St, Lexington, KY
The 21c Museum Hotel isn’t just a place to stay, it’s a place to see. Every corner of this boutique hotel pulses with artistic energy. I captured this image during a quiet moment in May 2025, while showing a friend visiting from London the side of Lexington most people miss: its bold, contemporary art culture.
The exhibit we walked through is part of a rotating annual installation that transforms the space every November. It’s free to the public, and easily one of Lexington’s most underrated gems. The walls speak. The lighting sings. You’re surrounded by thought-provoking pieces that make you pause and if you’re lucky, feel seen.
🎨 Pro Tip: Walk in like you belong. No reservations needed. Start in the main hallway and wander upward. You never know what piece will move you or move with you.
4. Historic South Hill – Hidden Harmony
📍 South Mill Street + Upper Neighborhoods
You’ll miss it if you don’t slow down. But that’s the point. I found this view on a spring afternoon, tree-lined streets, historic porches, a faint view of the Lexington Financial Center peeking through the leaves. This neighborhood is a time capsule with a heartbeat.
South Hill doesn’t scream for attention. It hums. The homes are old, yes, but full of character, painted by generations of families, porch plants, and morning routines. You might pass a grandmother watering flowers, or a group of students walking back from UK’s campus. That’s Lexington. Past and future on the same sidewalk.
🏡 Pro Tip: Start at Phoenix Park and wander south. Bring a camera and take your time.
5. The Square on a Rainy Night – Moody Lexington
📍 Corner of Main Street & Broadway
Most people put their cameras away when the rain hits. I keep mine close. This image was taken through a fogged-up window, looking out onto The Square after a spring shower. The reflections, the lights, the movement, it’s romantic in a way Lexington rarely gets credit for.
Rain reveals something in this city. It slows things down. It makes the colors richer, the lights softer, and the sidewalks feel cinematic. Nights like this, Lexington feels like a Southern noir film, moody, magnetic, meaningful.
🌧️ Pro Tip: If you’re nearby when it rains, don’t rush indoors. Grab a warm drink, find a window, and let the city tell its story.
6. The Secretariat Statue – Gateway to the Bluegrass
📍 Old Frankfort Pike
They say Lexington is the “Horse Capital of the World,” and this statue proves it before you even realize you’ve left the city. This stunning silhouette of Secretariat, arguably the greatest racehorse of all time is the first landmark greeting you as you drive onto the iconic Old Frankfort Pike.
Framed by open sky and Bluegrass fields, the statue feels more than symbolic. It’s a salute. To legacy. To power. To the land you’re entering. For me, it marks a shift in energy from Lexington’s urban heartbeat to its quiet, rolling soul.
📸 Pro Tip: Lay low with your camera in the early evening. Let the sun hit just right, and this statue becomes a silhouette of motion, not metal.
7. Castle & Key Distillery – Industrial Romance
📍 4445 McCracken Pike, Frankfort, KY
Tucked in the shell of a restored 1800s distillery, Castle & Key is more than a bourbon destination it’s a living piece of art. From the architecture to the small details at the tasting counter, everything here feels intentional. I captured this image during a quiet visit, drawn in by the light, the textures, and the bartender’s unspoken calm.
This is where you come to slow down. To sip something aged. To appreciate both the craftsmanship of the spirits and the space itself. Every corner is photogenic, but more than that, it’s designed to make you pause.
🥃 Pro Tip: Visit on a weekday. It’s less crowded, and you’ll have more time to appreciate the botanical trail, springhouse, and of course, the tasting room bar.
8. Cars and Coffee – Unexpected Lexington
📍 Southland Christian Church, Richmond Rd Campus (First Saturdays)
You wouldn’t expect it, but every first Saturday of the month, this church parking lot transforms into Lexington’s own auto runway. Vintage rides, European luxury, American muscle, all parked side by side, waxed to perfection. The vibe? Chill but passionate.
I love how this gathering brings out all kinds of people, families, collectors, young photographers, even casual onlookers. Everyone’s welcome. It’s loud, it’s proud, and it’s one of the most photogenic subcultures I’ve experienced in Lexington.
🚗 Pro Tip: Show up early for the golden light and fewer crowds. If you’re a photographer, the reflections off those supercars are gold.
