Lexington, KY


Curated by
James Carroll

1.0 miles
51 Points of Interest

Copyright 2020


You are taking this tour AT YOUR OWN RISK. Be aware of cars and other pedestrians. If you are walking slowly, move to the side. Do not stand in the middle of the sidewalk. Cross the street only at crosswalks. Put your phone down when crossing the street.
These are good rules for any downtown. Just remember, if you get squished it is your fault.

Table of Contents


We will start on North Upper Street, between Main Street and Short Street.

Upper Street

38.047562, -84.497531
Check the Map
Make sure you are on the sidewalk adjacent to the Old Courthouse. Ignore the main entrance for now, we will see it later.
There are five Points of Interest in this section.

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Short Street 1

Walk to face the arched entrance on the side.

Foliage and...

Take a look at the foliage detail around the doorway, starting at the bottom. Notice anything? It seems to get more finely sculpted and detailed as it goes up. Could this be by design? Or simply due to wear and tear?

Now look even closer at the top of the arch. What do you see? A face! There is a beast–perhaps a lion–peering out through the leaves.

And this is not the only face here. If you look farther up, past the balcony to the top center of the windows, you can see something that could be a face. It has a center detail that could be a nose, and two spirals that could be eyes. With the foliage below and to the sides it appears to be peeking out.

Now look to either side and you will see two gentlemen with large mustaches, glaring eyes, and stern expressions. If you look closer you will see that their mustaches are actually leaves!

Return to the sidewalk and look at the tall red brick building directly across the street.


The front of this building has been divided into section in a variety of ways. First we have the floors, and they have horizontal details that show the transitions.

Then it is divided into two unequal vertical sections. Why do you think this is? It might have been for two separate businesses, or separate sections of the same business; notice that the wider side has more ornamentation. The smaller side might have been a later addition. In any case, it makes the facade more interesting.

The windows are in sets of three, with each middle window wider than the other two; also, the middle brick dividers are wider than those flanking the window sets.

Look at the three columns on the fourth floor–specifically, their bases. The middle one has three toe-like details underneath. The left column only has two and the right one does not even have a base.

Turn left and walk to the corner. Look at the corner building that is directly across Short Street.

Not just boxy.

Notice how this building is mostly a plain brick box; the only real decoration is in the stone areas at the top and bottom. But if you look at the center of the wall between the last two top floors you will see a set of three proper ornaments.

They seem to be assembled from a variety of parts. The center horizontal bit looks like a spindle that was turned on a lathe. Descending from either side is a spiral column with a base; the bases are not resting on anything, so these could be tassels. A swag of leaves and ribbons hangs between them. Above, there is a pointed arch. Inside that is a thistle-like plant that has two peony-like flowers.

In between the ornaments and repeated just below the roof line you can see a diamond and square motif.

Remember this building. We will be seeing all four sides of it.

Walk to face the smaller stone building immediately to the left.


Where the previous building had almost no detail, this building makes up for it.

Just look at how busy the first floor is. The arch above the entrance rests on two square columns. Their capitals have loads of smaller details and they are close enough to see. There is a decorative band full of small details at the top of the windows. On the sides of the building the square columns become shallower Pilasters that lose their decorative capitals.

The two upper floors have details commonly found on bank or government buildings. There are two fluted columns with classical capitals holding up a triangular Pediment. The horizontal elements have Dentil blocks, including the Lintels directly above the windows.

Notice how I slid some architectural terms in? This will not happen often because I am more interested in shapes and volumes than trying to sound smart. However, sometimes they can help point out details.

Turn around and walk over to look at the back entrance of the courthouse.

A crowd.

How busy–there are twelve faces hovering over this entrance! Six on each side and sharing the same pattern. Look closely because each face is subtly different.

Short Street 1

38.047714, -84.497253
Check the Map
Return to the sidewalk, turn right, walk back to the intersection, and cross to the opposite side of Upper Street.
There are three Points of Interest in this section.

Skip to

Walk to face the second, very small building across Short Street.

Messick, 1928.

With such a large building right next door, it is easy to overlook this one–I did. But, look at the very top and you will see a stone block with the above name and date. This block is flanked by two scrolled bookends.

Continue walking along the sidewalk to face the third building past the parking lot. There is an alley-like opening immediately to the right and that is what we will look at.

Is that an alley?

Nope. Alleys do have to emerge onto a street, but this is another missing building. How can we tell?

Well, the right hand wall is rough and unfinished. But, a better clue is that horizontal section of bricks above the entrance. It is flush with the building on the right and has no independent supports, so it looks to be the remnant of a building.

Walk to face the entrance. Try to imagine what the front might have looked like. There would be a door and windows on the first floor, but did it resemble the building to the right?

Turn around to face the large parking lot behind you, and then look slightly to your right.


It is likely there were buildings here as well, with alleys running behind them. Now, we can get a different view–we can seethe normally hidden backsides of the buildings on Main Street.

And, they are lacking the ornamentation that we see on their fronts. That is okay because we are interested in the collection of their volumes, and there is a lot going on here.

What does that mean? Well, think of the buildings as blocks. They have different heights and widths and depths, and they are aligned in different directions. Plus, there is that really tall building behind them.

Can you see them as more of a sculpture now?


38.046872, -84.496263
Check the Map
Turn to your left, continue to the corner, and cross to the opposite side of Limestone.
There are two Points of Interest in this section.

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Church Street

Turn to face the corner diagonally across the street.

Streetscape one.

This is old school mixed-use–retail below and apartments above. There are wide sidewalks and outdoor seating. The upper floor are brick, but the first floors have a variety of details and colors and sizes.

Turn to your right and look at the two blocks on this side of the street.


Do you notice a difference?

The opposite side of Limestone looks like a neighborhood, and this side feels barren–that one is only here to take care of business and then go away. Of course, that is the purpose but the abrupt change is jarring; perhaps there could have been a gentle transition instead.

Church Street

38.047363, -84.495534
Check the Map
Cross to the opposite side of Short Street and continue walking along Limestone to the next intersection. Turn left and cross to the other side of Limestone.
There are five Points of Interest in this section.

Skip to
Market Street

Continue walking down Church Street.


Did you notice that this street feels different than Limestone? The street is narrower, the buildings–on both sides–are closer together, and there really is no traffic.

Stop when you walk past the last building on your left and you see a parking lot.

Backstage, part two.

Just like we saw the backsides of Main Street buildings from Short Street, now you can see the backsides of the Short Street buildings. The brick building that is just to the right of the beige one is the one we saw earlier across the street from the courthouse.

Look to the right and you will see another tall brick building. Notice how the center is indented to allow for extra windows. We will see this building later. Do you think it will look like this on the other side?

Continue walking to the stop sign.

Transition, part one.

Now we have a better view of the brick building. Notice how the stone surface has continued around the long side of the building but stopped at the back wall. Why?

The walls that do not face the street–and usually accessed by alleys–are simply structural, even if they are visible from other streets. Any decoration is better used on the sides with entrances. In this case the decoration just stops at the corner.

Cross to the opposite side of Upper Street and walk to face the back of the brick building.

Transition, part two.

Look at the upper two floors of the beige building just to the left. Notice how the two Cornices continue around the corner and then stops. It is easier to see on the larger cornice that they do not stop with a flat end; instead, each section of the cornice tapers off depending on how far it projects outward. This gives a nice finished look.

Now look at that other brick building to the right; it looks like that cornice just stops.

Turn back to look at the first brick building.

What used to be.

The back wall has three columns of windows. Notice how the rightmost column only has four windows. What do you see below them?

There is some discoloration that suggests there might have been a structure against the wall at one point. Perhaps the interior floorplan did not need or could not have windows on that part of the wall. In any case, this unexpected variation makes the wall more interesting.

Market Street

38.048693, -84.497003
Check the Map
Continue walking to the intersection and turn left.
There are six Points of Interest in this section.

Skip to
Short Street 3

Continue walking and stop just before the entrance to the parking lot on your left.


Turn to the right and look at the two buildings across the street. Look closely at the materials that make up the walls. What do they have in common?

Well, they are both sort of brownish-yellow. But, what makes them stand out is the color variations in their bricks / blocks. It makes the walls more visually interesting, and shows a high level of craftsmanship–it takes extra work to make sure the colors do not create a repetitive pattern.

Take a closer look at the smaller building on the right.

Is that original?

In particular, look at the brown brick sections surrounded by the black terra cotta. Do you think those are original to the building?

I like to think they used to be glass storefronts; maybe a barber shop or a drugstore or a hardware store. The business name would be painted on the glass. Perhaps there would be things displayed in those windows and people strolling by.

I have been reading Bradbury lately. Can you tell?

Okay, turn back to look across the parking lot.

One last time.

Look at the final wall of our brick building. That inset corner with all the windows has some visual interest, but the main part of the wall has just that skinny column of windows to break up all that brick.

You know what helps more. That shorter building in front–that is actually the bank building we looked at earlier. It sure is plain from this side.

But, it is not completely uninteresting. Look at the brick wall. What do you see? A building-shaped patch of discoloration. So, this parking lot was not always here.

Look at the tall beige building slightly to the right and behind the courthouse.

Transition, part three.

The upper floors have a lot going on and that makes the transition so much more noticeable. Try to imagine that all those details continued around the all four sides of the building. Would the building look better?

I do not think so. We might ignore them if there was nothing to contrast them with. And I think they serve a purpose. Even from this far away we know which side of the building to approach.

And we will see that building again.

Continue walking to the intersection.

Transition, part four.

Turn to look at the tall blue glass building. Now look at the shorter red brick building just to the right of it. What a nice composition the make–the blue helps make the brick color POP.

But, that is not what we are interested in. The brick building has some nice details–which we will see later–that use the same transition. This time, however, the bricks change to a darker color. That helps them recede from view so you really just notice the ornamented side.

Did you notice that shorter pointy-topped building beside it? We will see that close up later. I promise.

Turn right and look at the building on the corner directly across Market Street.


Notice how this building does not seem to have a plain section of wall at all–everything has some sort of visual detail. And it does this without contrasting colors, just shapes.

Then it has that curved corner. While other buildings stick to right angles, here one wall flows smoothly into another.

But there is a lot more to see.

Short Street 2

38.048198, -84.497686
Check the Map
Turn right and cross to the other side of Market Street.
There are six Points of Interest in this section.

Skip to
Short Street 3

And stop.

That entrance.

Like the bank entrance before, this has loads of details: pilasters and columns with decorative capitals, rough-cut stone, an arched entrance, and a very ornate Corbel between the door and window above.

We have seen faces on the courthouse, but not with the detail that these two faces have. They are carved realistically and this sometimes means they are the likenesses of actual people.

Continue walking along the building to the next entrance on your right.


Or decorative details with dragon-like faces. The left one looks friendly, but the right one looks a little upset. Perhaps it is annoyed with the incessant happiness of the other...

Continue walking to the next entrance on your right. This is for another building.


This is quite the opposite of the whimsey of the last two entrances. There are lots of hard edges and straight lines, and the elements are oversized enought to feel, well, solid.

The darker stone helps with this effect, and we will see this building again later from the other side of the street.

Continue to the intersection and look at the buildings diagonally across the street.

Streetscape two.

This is a collection of small buildings that create a pleasant neighborhood street. They have a nice variety of shapes, colors, and styles. If you look very closely at the tops of the upper windows on the corner building, you will see a line of gentlemen with very large beards.

Cross Mill Street to continue along Short Street. Stop just before the entrance to the second parking lot on your right.

A ghost...

sign, that is.

Look at the upper left of the brick wall on the far side of the parking lot. You will see a faded sign for Uneeda Biscuits.

Is is Uh-needa or You-needa? I keep reading it like the first but the second sounds better.

Continue to the next intersection. We will make a quick detour before heading back down Short Street. Turn right and walk to face the second building across the street.


The very nice marquee makes sure you will not miss this building. We are interested in the ornamentation at the top of the building.

It is a collection of smaller, sometimes exuberant details. Look closely inside those four triangles above the building name; they appear to be more faces!

Short Street 3

38.049448, -84.499157
Check the Map
Walk back to the intersection and cross to the opposite side of Short Street.
There are four Points of Interest in this section.

Skip to

Before we start walking back, look across Short Street.

Streetscape three.

There are only three buildings this time but they are older, original buildings. Notice how the smaller middle building feels kind of squished between the larger ones.

As you walk past it you can see that it has a sloping, rather than flat, roof that leaves room for another Uneeda ghost sign. This is another example where the shapes and volumes of each building play together to make a sculptural whole.

Oh, that sounded really Art School. I am not sure yet how to explain this idea better–I will edit this when I figure it out. But, basically, when you are walking around a built environment and see a collection of things, try to see them as if they were in an art gallery.

Continue walking past the parking garage, the tiny parking lot, and the first small building. Stop when you can see fully see both sides of that brown building diagonally across the street.

The other side.

Remember that brick building with the center cutout we saw from a distance? This is that building. Apart from the entrance we saw earlier it does not have a lot of ornamentation. Even so, it is a handsome building. Why?

I think the brown color feels more stable and grounded than the various brick colors. Notice how the first two floors extend back a bit; this gives the building a larger and more solid foundation. Then look at the height compared to the width and depth; the proportions just feel... right somehow.

Walk to the intersection, cross Mill Street, and then walk to face the Dragon entrance of the second building across the street.

One or two?

When we walked past this building earlier it seemed to be one long building because the looked like they belong together. But when you look at the upper floors they do not look alike even though they do share some details.

Perhaps they are one physical building and the details hint that each section had a different function. Perhaps they are two separate buildings built by the same owner and architect. Perhaps one side was built after the other.

Continue walking and stop just past the pavillion. Look across the street at the bank building we saw earier.

Skin deep.

We have seen this building from two other angles and here we get to see the reality–that no matter how interesting the front of the building is, it is just a brick box with a veneer applied.

Sometimes, the interior is destroyed and this veneer–the facade–is left standing. Louisville has some good examples of this. It preserves the streetscape and allows for a new interior to be built later.

And as we have seen, sometimes the veneer is changed when the business changes.


38.048304, -84.497888
Check the Map
Turn to your right and walk between the courthouse and the pavillion. Turn right at the end of the pavillion.
There is one Point of Interest in this section.

Skip to
Main Street 1

You will see the two buildings we saw earlier. Walk to face the small white building on the right.

Top to bottom.

Notice how the amount of detail seems to increase from floor to floor? The first floor is mostly windows, the second has more, and the third absolutely explodes with details. So we will start there.

The horizontal cornice below the attic windows is a line of brackets. The two pilaster capitals have broadly carved, stylized elements. The arched windows have oversized keystones and the center arches are supported by mini columns. It might not be easy to see, but even the flat, plain surfaces are dimpled and textured.

On the second floor the windows have smaller details on the top and sides. The pilaster end midway as if they just emerged from the wall. However, they do each have a small stylized lion head.

The first floor may be mostly windows but the three pilasters do hold surprises: their capitals have faces! The two flanking the entrance are larger, stylized, and more fully realized. The rightmost pilaster has a smaller contemplative gentleman.

Main Street 1

38.047827, -84.498555
Check the Map
Turn to your left, walk to the corner of the next building, and turn right.
There is one Point of Interest in this section.

Skip to
Main Street 2

Walk to the entrance on your right.

Classic details.

You might have noticed the marquee on the smaller entrance around the corner, but this one is larger and has the same details. The entrance has the same blocky elements that are visible on other buildings, but the columns stand out.

It is actually the column capitals that are unusual. The scrolled bits on the corners are classical, but the earring-like swags hanging from each are unusual–the first time I saw them was outside the Missouri History Museum in St. Louis.

Main Street 2

38.048054, -84.498992
Check the Map
Continue to the intersection. Cross to the opposite side of Main Street, turn to your left, and walk to the entrance of the parking garage on your right.
There are eight Points of Interest in this section.

Skip to
Main Street 3

Turn to your left to look back at the building we just visited.

A postcard view.

Of all the buildings and views downtown, it is this building that most makes me think of one of those old hand tinted postcards.

It has that multi-story light stone base that really anchors it to the ground. The vertical supports have solid proportions and there are plenty of horizontal lines that continue to tie it to the ground.

The middle brick section has that particular brick color that you find in those tinted postcards–a color we have not seen anywhere else downtown. And it, like the base below, has that nice solid ratio between height and width and depth.

Then the upper floors have that particular tan / beige postcard color so it looks vintage even now. Nothing really draws attention to itself; instead, it is just the general busy-ness of the whole area. And if you closely you can see that the wider sections have vertical hanging swags like we saw on the columns below.

Boy, did I say THAT enough?

Continue walking to face the courthouse. You might not get a perfect view because of the trees and the parking garage entrance.

Old courthouse

This is a chance to see the entire front of the courthouse. However, it is not the best view–we will see that later.

Continue walking past the parking garage and stop at the corner of the next building on your right.

Small details.

The first thing you might notice is the windows; they have arches within arches. Next you might see those large brackets at the roof line. Now, look closer.

There are smaller bits of detail all over the place. The larger ones are above the arches, then the pilaster capitals, and the really small details on the horizontal bits.

Now, look at the tall building diagonally across the street.


We have seen this building from a distance. It shares some of the same features as THAT previous building: a multi-story base, a plain middle section, and an upper section with some details. But there are differences.

The base might be too tall for the width and depth, and it does not look that different from the middle section. The middle section is taller as well. The upper section does not have the same ornamentation, but the cornices at the top and bottom do make it seem like a definite separate section of the building.

Now, it is not fair to say this building is not as good because it does not look like the other. It is meant to be taller and has proportions to match. The extra height in the base makes it FEEL taller, and if it were shorter might make the middle section look too willowy.

Cross to the opposite side of Upper and walk to face the small building to the immediate right of the tall building.

What is missing?

Do you see it? Or, not see it?

It is missing an entrance. This small building is most likely attached to the tall building, but the details do not match. Perhpaps it was built later. The bricks look similar and the windows are painted the same, but still.

And notice those star details above the first floor. The star on the far right is cut in half. The stars are centered between the windows, so the windows are not themselves centered in the wall. Could there have been another part that is now gone?

Or, is this building part of the building on the left? They are the same height...

Walk to face the dark gray building to the right.

Details, not details.

There are a lot of smaller details here but the single color makes them difficult to notice. The windows are obvious and the columns maybe because of shadowlines, but otherwise you have to stop and really look.

Walk to face the third building on the right.


Even across the street, those are what you see first. Then it is that large horizontal element that divides the columns. Notice how it looks like the second floor is set back from the first and how it makes the entrance seem more solid.

Continue walking to the corner and look back at the line of buildings across the street.

Streetscape four.

Each building has a differnt style, but it is the different heights that is most noticeable.

Main Street 3

38.046442, -84.497016
Check the Map
Continue to the intersection. Cross to the opposite side of Main Street.
There are four Points of Interest in this section.

Skip to
Old Courthouse

Walk to face the fourth building on your right–the one with the columns.

More than columns.

Now that we are closer, check out the details on the second floor. Usually these details are higher up so it is easier this time.

The column capitals have those hanging swags. However, the individual elements are more detailed. For instance, look inside those corner scrolls–they have leaves following the scrolls.

The keystone above the center window would be enough, but it has lots of floral details. Then it is flanked by even more floral details, and the window is bordered by a floral swag.

Walk to face the building immediately to the left.

Brick details.

We have seen arched windows before, but these are interesting because the arches are made from bricks.

It is easy to think of these rectangular bricks as only good for plain, flat walls–like we have been seeing. When you start looking closer they can be used for all sorts of building details, some–like these arches–very un-bricklike.

And notice how paint is used to accentuate the surfaces that are projecting out from the wall.

Walk past the parking lot to face the dark gray building again.

Is this better?

Are the details more easily seen from here?

Old Courthouse

38.047277, -84.497891
Check the Map
Cross to the opposite side of Upper Street.
There are six Points of Interest in this section.

Skip to
The End

And stop.

Photo op.

This is THE best view of the courthouse, so you can move around to get the best angle.

Turn to your left and walk to face the main entrance of the courthouse.

Really solid.

As you walk up, pay attention to the outer wall of the staircase. First, it is seriously solid looking, like it could be part of a castle. Since it is an outside wall it could have been just plain blocks, but the center section has those inset brackets that suggest Crenellations.

Continue to the short flight of stairs.

The lamppost bases.

I think the only plain surface here is the top! The corners have lion heads attached to square columns that are perched on inverted brackets.

Since that is not enough, each side has a Cartouche. They have either "1899" or "FC". There is a pair of swag tassels on top, and those are held apart by the lions.

Walk to the left side of the stairs.

The planters.

It might sound mean, but I think the plants are actually a distraction here.

We will start with the side facing the building. This side has a female face above a shield.

The next side has a shield with an eagle perched on a handle above. The eagle is looking toward the street. The opposite side has a similar eagle looking the same way.

The last side has a male face above a shield. You can see the stern faces of the eagles from this side.

The planter is held upright by a base of four horizontal brackets. But that is not all–look at the top of the brackets. There are four-toed FEET. With claws.

And, because that we can not stop there, the planter on the other side has completely different face sides!

Look at the brackets above the door.

The brackets.

We saw face brackets at the back entrance and there are more here. But instead of six brackets with three faces, there are four with three. These faces are less realistic and most are having bad hair days.

Look down to the arch above the doors.

The entrance, part one.

The outer details looks like linked cartouche charms. The inner cylindrical element follows the curve of the arch and has an intricate floral / scroll design; notice how the design flows smoothly across sections.

Can you imagine the amount of work it took to carve each section?

Finally, look at the entance.

The entrance, part two.

Well, actually, just the horizontal band at the top of the columns. The columns are just columns and are there to hold up the good stuff.

You can look at either set of columns; we will work outward from the doors. First there is a serious face overlooking the entrance, then a ferocious looking lion face glaring down the stairs, and then a pair of faces–one happy and the other looking annoyed.

As the band moves to the wall you can see a pair of heralic gryphons flanking an "FC" emblem. Like the faces before, they are surrounded by foliage.

Just think–it might be possible that people have walked through these doors without ever noticing all these details watching them!

You are done!

Walk around to the right side of the building and you are back where you started.


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