Winchester, KY


Curated by
James Carroll

0.75 miles
46 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


Make your way to the downtown parking lot on North Main Street. It is directly across the street from 18 North Main.

North Main Street 1

37.994068, -84.176541
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We will start at the brick-lined entrance to the parking lot.
There are eight Points of Interest in this section.

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North Main Street 2

Look directly across the street at the building with a bay window.


The most interesting part of this building is the detail at the very top. It has the general shape of a headstone, but these sort of topknot details are actually common. They can include a business name, or an street number, or a name.

Turn right and walk to face the building with a large marquee hanging over the sidewalk.

Bricks, part one.

Look above the windows that are above the marquee. You might think that brick walls are simply flat planes with cutouts for windows and doors. Not always.

The windows are set in recessed spaces and the brick courses just above the windows are gently brought outward to the main surface plane. For interest, alternating bricks are brought outward even more to create a checkerboard pattern. Then, as the wall transitions to the roof line, bricks are pushed forward to create bracket-like shapes.

Turn around to look at the building directly across the street.

Bricks, part two.

This building has the same brickwork running across the its top. If the sun is shining you can see how the various brick depths create some nice shadow lines.

Walk to stand in front of the dark brick building that is just before the Leeds marquee. Look directly across the street.

Downstairs, upstairs.

Notice how the ground floor is very plain compared to the uppper floors. Those brick Pilasters give a bank-like feeling to the front, as does the horizontal band of tiles above them.

Then, there is a series of bricks set diagonally, creating a hatched effect. Above that is a line of brackets supporting a Cornice. And, finally, there is a name set into a brick Parapet that spans the width of the building.

Turn to your right to look at the Leeds marquee.


Like the Kentucky Theatre in Lexington, the Palace Theatre in Louisville, or the Crump Theatre in Columbus, theatre marquees are the highlight of any street. There are the colors, the flashing lightbulbs, and the vertical name.

As you look over to the building notice the different types of support bars and wires there are, and where they are attached to the building.

Like the previous building, the upper part has a different facade style. This one is covered in terra-cotta tiles, giving the effect of solid stone blocks.

Walk to stand under the marquee and look across the street.


It looks like there a horizontal detail missing between the two rows of windows. At the top is another very ornate Cornice. This one is supported by four larger brackets, with decorative panels between them.

This topknot has a name and a date.

Walk to face the next two buildings to the immediate right.

One or two?

This is either two buildings that each have three columns of windows, or a single building with six. While the ground floor makes this seem like two buildings, the roof line details run the entire length and do not change.

Then, the double brackets look like it could be two buildings with identical facades, but the bricks below do not have a seam. There is a door immediately below that leads to the upper floors, so that is most likely the reason for the extra width.

Turn right and walk to the intersection. Look at the dark brick building across the street.

Brick details.

This is a good example of a basic brick wall. Until, you look at the area above the topmost windows.

Each of the vertical elements has bricks that are set vertically in a triangular 1-3-5 pattern. The courses above the windows are interrupted with two bricks set diagonally to create diamond shapes. Then, bricks are set to form a horizontal serpentine pattern across the wall. Just above that, pairs of bricks are set forward to create a line of Dentils.

So, brick walls can be plain and ignorable, but will often surprise you.

North Main Street 2

37.995215, -84.176167
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Turn left and walk to face the Leeds Theatre.


From this distance it is easy to see the upper level as a whole. It has arched windows on either side; each windows has a panel with an urn and draped cloth. The center section has four Pilasters with a tall Entablature. And then, there are those semi-circular cutouts to break up the straight lines.

But, there is something unusual. You might have to back and forth a bit, but look below the arched windows. There is a triangular detail that looks like it might be covered over.

Is it possible that the ground floor has the same sort of detailing? Otherwise, why is that triangular bit there?

Continue walking along the sidewalk. Pass the building with the bay window. The next building is a single story yellow brick building; stop at the other corner and look up.


Actually, look at the space between the buildings. The red brick from the next building continues, but only on the ground floor and then there is a roof.

But why? The space is so narrow–too narrow for an alley or a sidewalk–so why leave a gap. One of the two buildings could have been widened to fill the space.

Walk past the building on the left, and stop at either end of the second building.


You can go to either side because we are looking at the Pilasters. Specifically, the two floral details.

Continue walking to the corner. Look to your right at the entrance.


Usually, stone details are finely carved and full of small details. Not here. These are chunky and blocky and look barely touched with a chisel. And yet, they are a nice contrast to the meticulous brick courses.

Turn to your left and look diagonally across the street.

Street view 1.

If you can avoid the traffic–or just ignore it–this may be THE shot of downtown Winchester.

South Main Street 1

37.993459, -84.177108
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Cross to the opposite side of Broadway Street.
There are two Points of Interest in this section.

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Cleveland Street

Walk to face the third building across the street.


This is such a traditional storefront. The display windows out front, the single-door entrance, and the tall door on the side that leads to the upper floor. Notice how the angled sidewalk contrasts and draws attention to all the horizontal lines at the entrance.

Then look at the top. But notice how the details are on the simple side, and the paint makes them look more complex.

Look at the very topmost point and let your eyes slide to either side. See those details poking up from the corners? If you do not look directly at them they look like horns; if you do they look like butterfly wings.

Walk to the corner. Look at the building across the street at the opposite end of the crosswalk.

What an entrance!

It feels like this might have been a department store–look at all those display windows. And how the ceiling sections are arched; this is a nice contrast to all the right angles. There is no exterior door to the upper floors, so perhaps there was a large staircase going up.

As for details, look at the upper two corners. There is a pair of very detailed cornices, but notice how they do not connect. In fact, they do not even go to the edge. And then there are the two swags underneath with their wafting ribbons.

Cleveland Street

37.993118, -84.177283
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Turn around to walk down Cleveland Street.
There are eight Points of Interest in this section.

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South Main Street 2

Walk to face the entrance of the second building on your right.


The first thing you might notice on this arched entrance is the Keystone. The scroll detail makes it feel like a bracket. It has a floral Swag draped in front. There are two leaf structures branching out from the bottom but look closer; the joint runs through the leaves, so they are actually part of the flanking blocks.

The alternating keystone-like blocks draw attention to the fact that the arch is made of separate blocks–normally the joints are more discreet. But all the right angles and straight lines contrast with the curves of the arch to hightlight each block.

Walk to face the entrance of the next building on the right.

Post Office.

More classic design. There are six large columns supporting a heavy Entablature. In fact, the stone blocks and scaled-up details make the whole building feel solid.

Now look at the detail above the door. We have all those somewhat geometric details and here there are curvy lines and leaves. This is not bad, just not as solid. Also, the whole element is slightly wider than the door frame, so it feels like crown.

Imagine the curvy bits are gone and the Cornice is narrower–it would blend in with the rest of the details. Perhaps that is why the it is there.

The leaf detail is called a Palmette.

Remember this. You will see them all over the place. They are especially popular in cemeteries.

Walk to face the lamppost on the right.


These lampposts have feet. I do not mean projecting bits that touch the floor–actual feet. With toes. And claws. Now, I am sure they do not need toes or claws to stand upright, and it is always disconcerting to see them. Why feet without the rest of the animal?

Now look between the legs. What do you see? Where you might expect a fig leaf there is another Palmette.

Told you.

Walk back to the sidewalk, turn right, and walk to the corner. Look at the building diagonally across the street.


This building is basically a big brick box without a lot of details. Sure, there is a decorative Cornice at the very top but just simple arch shapes and windows below.

So what do you do? Paint. It highlights the geometry on the facade but it really adds to the side. Those arches are simple half-circles, but the paint brings them, the wall above them, and the cornice into a single large detail. Do you see it?

Cross to the opposite side of Cleveland Street. The courhouse is on your left. Walk to face the entrance.

Courthouse, part one./h4> Just look at the building and notice what you like or do not like.

Walk back to the corner at Cleveland Street. Look at the tall building across the street–the one with the entrance.


Downtown buildings are generally brick boxes. The interesting front of the building–the facade–is just a veneer. All the ornaments and color disappear at the corner and then it is just plain old basic bricks.

But, this time the bricks have different colors so there is some visual texture.

Walk to face that tall building.

A different view.

We looked at the entrance before. Does it look different now? Maybe a little prickly or thorny? All those rectangles pointing inward feel like they might be trying to keep something in.

Look at the windows above the entrance. They each have a keystone bracket, this time with a different leaf type at the bottom.

Now look just to the left at the details between the windows. What do you see? More Palmettes.

Three times in one block. They are like Kudzu in the South.

Turn right and walk up to the intersection.

Street view 2.

With the elevated sidewalk and traditional details, this part of the street feels like it could be from a small New England town.

South Main Street 2

37.992992, -84.177336
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Turn right.
There are three Points of Interest in this section.

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Court Street

Walk to face the courthouse entrance.

Courthouse, part two.

Look at this side. Does this side feel different from the other side? Perhaps that each side has a different use?

I think this side–the side that faces Main Street–is meant for business. You are downtown to get something done and this is where you start. The other entrance–that has a lawn and those curving staircases–is more grand and better for speeches and photos.

Turn around to face the buildings on the opposite side of Main Street.

Street view 3.

Just look at the variety of colors and shapes and details.

Turn right and walk to the corner. Turn left and look at the building on the other side of the crosswalk.


What is the first thing you notice? I bet it is those bay windows. They are so large they seem to be bigger than the building itself. They certainly leave no room for other details.

However, they did not succeed.

See those little blocks at the top and bottom of the Pilasters? The top center one is different–it has a portait. Now look just above that. You might notice those four four swags, but look closely at the detail in the center. It is a Green Man. His face is made of greenery.

You can also see, on either side, a pair of cornices. While they looked a little strange on a flat roof line, they make sense with the shapes here.

Court Street

37.992645, -84.177518
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Turn to your right.
There are three Points of Interest in this section.

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South Main Street 3

Look at the building directly across Court Street.

Rough and smooth.

The ground floor is a seriously heavy and solid foundation. If the blocks were smooth they might still feel solid but the roughness brings a little something extra. If there were no windows this would be a great base for Keep.

And it is tall. Just look at the front door for a sense of scale. The entrance is not being shy either–that is a lot of stone for such a small door.

The upper level, with its smooth brick surface, seems even more secure way up there. It does not have to try because you would have to get past the ground floor first. Even so, it is not slacking. See the turret on the corner? It has Crenellations. One could imagine a guard up there keeping an eye out for invaders.

Walk down to face the brick building just behind.

Where to start?

How about the bricks? They look like the bricks that that tall white building from before used for its sides. This building is so confident they are Right Up Front. So confident it does not need any superfluous colors, either.

It has a taller-than-necessary ground floor. After all, it does have to compete with the Keep next door. The middle section has two floors. Notice how the upper windows are taller. The sign does say "Fraternity Building", so perhaps the lower floor is offices and the upper is a big open area–maybe even taller than the windows because there is more building above.

Then there are six large brackets below an even larger Pediment. And there is still building behind there; perhaps it is a large and dusty attic full of cobwebby antiques.

After all that, there are still a variety of smaller details scattered around. This is definitely no wallflower.

Take a quick look at the top point of that Pediment. What do you see? Yet another Palmette. They are absolutely the Smiths of details.

Walk back up to the corner, turn right, and cross to the opposite side of Court Street. Do not look up yet.

Close ups.

If you would like to see the last two buildings closer up, go ahead. I did. Twice. Just come back to this corner.

South Main Street 3

37.992645, -84.177518
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Make sure you are at the corner of Court and Main Streets.
There are ten Points of Interest in this section.

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South Main Street 4

If you have not done it already, look up at the corner entrance.

A face.

You might have already noticed this, but it is worth a big reveal. So, act surprised like it is Christmas morning and you peeked.

This is a face that could be on a gold coin. It is in profile with a classic hair style and even has a coin-like detail above. Then there is a jungle of flowing foliage to cover up the otherwise plain surface.

Take a quick glance at the column. See all those little divets? How would you like to be the one that had to pop all those little chips? Not me.

Walk around to look above the other column.

Another face.

You might be tempted to think that it is the same face. It is not. Nor are the details. See the circles in the ring above the head–they are rectangles on the other side. The foliage might be similar but not identical.
Take pictures and compare them. I did. But just the once.

Turn to face Main Street. Look at the tall building on the other side of the crosswalk.


In Prague, it seems that there is a law that any plain wall must be immediately covered in ornaments. And not just Palmettes. That is not a complaint, but I think that inspired this building.

The upper stories have arches, keystones, and Pilasters. And, normally, that would be enough. But, someone came by and decided that the ornaments needed ornamenting. So the arches got smaller arches, the keystones got a smaller keystone detail, and the rectangles in the Pilasters got Letterpressed.

Again, not complaining.

Walk to face the next two buildings on the right.


We all know that bricks walls are held together with mortar. It is there but the bricks are the focus.

Not here. The mortar has decided to rise up–or out–and let everyone know It Is Here. What it does not know is that each and every brick is even more visible now instead of blending together into a unified mass. We can really see how the bricks are put together.

Could this be another single building that looks like two? I am not sure.

Walk to face the building on the immediate right.

Not mortar.

See the difference? We can see individual bricks in the details, but not really in the wall. But that is not why we stopped.

See those greeny-browny rectangles below the brick part? See the horizontal seams on them? Those seams are not random–they have a pattern. The widths of the rectangles might vary but not the pattern.

And then, look at the grid below the rectangles. Can you read the letters?

Walk to the other side of the marquee and turn left to face the tall building across the street.

One vs two.

Not to be outdone by its neighbor down the street, this building decided a large two-story bay window instead of two single-story bay windows. And it is impressive. And, like before, it did not leave room for details.

There is another pair of cornices, this time sporting moustaches.

Turn around to face the building behind you.


This is another complex facade. The ground floor has more rough stone blocks, so it feels solid. If you look at the Cornice under the windows you will see that the Dentils have rough faces as well. And so do the stones between the windows.

If you step away from the building and look up you can see a decorative panel between the two sets of windows. Amongst the swirling foliage you can see a book, an eye, and a violin.

Walk to face the wide building across the street.

Definitely one.

There is no doubt that this is a single building, even though there are two separate storefronts. I like how the details flow up one side of the building, across the top, and back down the other.

There are some nice uncomplicated details. The bricks that outline the tops of the windows are themselves outlined by bricks. The large Cornice at the top is suppported by brackets of different sizes. The small windows below it have scrollwork underneath. And the center window has a date above and a lattice for more visual texture.

Walk to the corner and cross to the opposite side of Lexington Avenue.

Street view 4.

Look diagonally across the street for a long stretch of historic facades.

Cross to the opposite side of Main Street.

Street view 5.

Look diagonally across the street for another set of facades.

South Main Street 4

37.991712, -84.177736
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Cross to the opposite side of Lexington Avenue.
There are seven Points of Interest in this section.

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The End

Look diagonally across the street at the top of the building there.


On most buildings the cornice would continue around the corner. Perhaps it was difficult or very expensive to create a curved cornice, or maybe the emblem was always in the plan, but the result is very elegant.

The two cornices come right up to the emblem and then return. If they had met it would have been just another cornice that might be worth just a glance.

Walk to face the tall building across the street.


Now we can see this building completely. The facade reads like a quilt; where other facades are defined by the details projecting from it, this one just has different visual textures separated by horizontal elements.

The ground floor has the rough stone, then five windows separated with rough stone, then horizontal stone, then bricks and windows, then the checkerboard pattern and finally small vertical rectangles.

Walk to face number 47 on the right.


These capitals have lost some of their details. They are assembled from individual elements and many have gone missing over the years. It would be easy enough to replace the elements and make the capitals look new, but these imperfections add a bit of character.

They also help us see that the building does not just look old, it is old.

Turn around to look at the Keep directly across Main Street.

Why is that there?

Look above the windows that are just to the left of the turret. It appears to be a balcony with a metal railing. However, there is no way to get onto the balcony at all. How strange.

Turn back to your right and walk to face the building with the two bay windows. Look back at the Keep again.

Street view 6.

This is the most interesting corner so far.

Walk to face the entrance of the court house.

Street view 7.

Look to your right.

Walk down to the corner and look at the building diagonally across the street.

Kerr building.

Like the Brown-Proctor building we saw earlier, this building has a curved corner. And, like before, the roof line details was not carried around the corner. Instead, there is a checkerboard panel of rough stone blocks; this catches the eye better than another section of bricks.

But, the brick details on either side are nice. They are deep enough to create some large and not-at-all-subtle shadows. And then there are the scooped-out areas of the top edge that break up that long straight edge.

You are done!

Cross to the opposite side of Broadway Street. Continue walking until you see the parking lot on your right. You are back where you started.


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