Winchester, KY

Downtown


Walking Tour
2015

0.75 miles
21 Points of Interest


For demonstration purposes only!

Rules

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

Start

Make your way to the downtown parking lot on North Main Street. It is directly across the street from 18 North Main.
This is a space for any text that does not belong with the official information.

North Main Street 1

37.994068, -84.176541
Check the Map
Walk back to Main Street. We will start at the brick-lined entrance.
There is one Point of Interest in this section.

Skip to
North Main Street 2
Turn right and walk to the very visible theater marquee. About halfway up the block you will see a pedestrian crosswalk on your left.

Leeds Theater.

Built in 1925, Leeds Theater was one of three movie theaters in town and continued to operate until 1986. It was one of the first buildings in Winchester to have air conditioning.

North Main Street 2

37.994416, -84.176580
Check the Map
Walk back to the pedestrian crossing to cross to the opposite side of Main Street.
There are two Points of Interest in this section.

Skip to
Cleveland Street
Turn left and walk to the third building; it has full height glass windows. There is a historic marker on your left.

Pastime Theater.

The Pastime Theater, a popular movie place in town, was the site of possibly the worst disaster ever to strike here. March 9, 1918, sixteen people lost their lives, and an untold number of others were seriously injured when an extension to the theater collapsed.

The prelude to the disaster began when fire gutted the building next door leaving the high, unsupported masonry wall standing next to the theater. That afternoon, violent winds and heavy rains caused the wall to wobble and collapse.

Continue walking along the sidewalk to the corner. Look at the long brick building on your right.

Kerr Building 1.

The building was referred to as a “business block.” Smith P. Kerr erected it in 1889 with the intention of housing many commercial businesses. When all of the area could not be rented, the building became the site of the Eclipse Flour Mills. Town Branch, the major source of water for the first settlers of Winchester runs underneath this building.
I split the original data because you can't see the rooster from here.

Cleveland Street

37.993118, -84.177283
Check the Map
Cross to the opposite side of Broadway Street. Continue walking to the next intersection.
There are three Points of Interest in this section.

Skip to
Wall Street
Turn right and walk to face the second building on your right.

McEldowney Building.

This is Winchester’s tallest building and was built for one of Winchester’s prominent citizens, M. T. McEldowney in the early 1900s. It was the first building in town to have a reinforced concrete frame and an elevator.

The surface of the building is detailed in the Beaux-Arts classical manner inspired by Italian Renaissance palaces. It housed barber shops, real estate offices, insurance agencies, dental and law offices, and other professional businesses including the U.S. Forest Service.

Continue walking along the sidewalk and down the stairs. Stop at the next building on your right.

Clark Judicial Center.

Hailed as one of the city’s most beautiful buildings, it was completed in 1913. It is an example of Parisian Beaux-Art and is constructed of brick with a marble neoclassical facade. The building served as a U.S. Post Office for 78 years before becoming the James Clark Judicial Center in 1990.
Continue to the corner and look at the building diagonally across the intersection.

The Winchester Sun.

This large commercial structure, “one of the best business houses in the city,” was originally leased to Parrish & Bradless, who ran a wholesale grocery and hardware business in the early 1900s.

It was constructed in 1908 on a site formerly occupied by a jail, jailer’s residence and a place to hold slaves during the slave trade. The Winchester Sun is the oldest business in town, being over 100 years old.

The first published newspaper was known as “The Smooth Coon” in 1878.

Corner buildings look best from across the street and this is the best view.

Wall Street

37.993192, -84.177910
Check the Map
Cross to the opposite side of Cleveland Avenue.
There are two Points of Interest in this section.

Skip to
Court Street
Look at the statue to your left.

Courthouse 1.

The back lawn is the home of sculptor E.M. Vesquesney’s famous World War I statue. The Doughboy faces to the north and has a plaque on the north side listing the names of Clark Countians “who gave their lives in defense of humanity in the World War.”
This was part of the single Courthouse description. The clock is best viewed from somewhere else so it becomes another stop.
Continue walking along Wall Street to the next intersection. Turn right and cross to the opposite side of Wall Street.

City Hall.

City Hall was constructed in 1912. The building has a combination architectural design, complete with tower and round-arched openings. The city’s police and fire departments were housed in this structure until the late 1970s. Following a recent rennovation, the first and second floors house a number of city offices.

In the early 1990s the bell was removed from the bell tower and placed on ground level in front of the building.

This building could be viewed from across the street but I thought that people might like to see the bell up close. Plus, there is no crosswalk from the opposite corner to the other side of Court Street.

Court Street

37.992734, -84.178263
Check the Map
Walk to the left side of City Hall and past the utility pole. There is no crosswalk, so carefully cross back to the other side of Wall Street.
There are two Points of Interest in this section.

Skip to
South Main Street 1
Walk to face the first two storefronts on your right.

22 - 26 Court Street.

The east side of the commercial block was constructed prior to 1886, and a matching west side was built just before 1895. The west building has rock-faced stone lintels and sills, while those on the east half are smooth. The east section was a tailor’s shop and the west section was the office of the Winchester Sun in 1901. The west section was known as the “Police Court.”
Continue along the sidewalk to face the tall brick building on your right.

Fraternity Building.

This handsome four-story structure, built as the Masonic Lodge, was called the Fraternity Building because it was used by most of the sororities and fraternities of Kentucky Wesleyan College. The Edgington Funeral Home occupied the first floor until 1948. The building itself is brick Classical Revival with a fine terra cotta decoration.

South Main Street 1

37.992515, -84.177578
Check the Map
Continue walking to the next corner.
There are four Points of Interest in this section.

Skip to
South Main Street 2
Turn to your right to look at the building on the corner.

Citizen's National Bank.

Built between 1886 and 1889, this building is one of the most impressive historic commercial buildings in Winchester. Rusticated stonework, carved medallion faces, decorated gables and elegant ironwork are featured in this majestic building.

The medallion faces seen on the arch over the entrance are of Lizzie Winn and Mary Miller, daughters of Dr. Washington Miller and Col. R.N. Winn, founders of the Citizen’s National Bank.

This building replaced an earlier bank building that was constructed soon after a disastrous fire of 1855, which destroyed this block of Main Street. The third floor and extending turret were removed in the early 1990’s due to extensive water damage.

Continue along Main Street to the canopy hanging over the sidewalk.

Canopy.

As you look above the second-floor windows, you will notice the intriguing feature of a fine early canopy supported by long chains. The end blocks of the canopy have pineapple finials and ball pendants. It was built around 1890 and later served as a billiard parlor followed by the Winchester Candy Company.
Walk to face the very next building to the left.

Odd Fellows Building.

This building is easily the most distinguishable building in the downtown area. Designed and built at the end of the 19th century, it has an elegant and well-executed design; featured above the second floor windows is a unique motif including a book with initials, an eye with radiating rays and an hour glass.
Continue walking to the corner and look at the building diagonally across the street.

Winchester Opera House.

Also known as Simpson’s Music Hall, this large brick structure was built for James D. Simpson, the first mayor of Winchester. Originally, the stage was set against the rear east wall, and the entrance was on East Lexington Ave. The Main Street side of the building was occupied by storefronts and in 1901 was the location of the Post Office. Housed there also has been a confectioner, a pool room and Dinty Moore Restaurant.

South Main Street 2

37.991865, -84.177679
Check the Map
Turn left and cross to the opposite side of Main Street.
There are seven Points of Interest in this section.

Skip to
The End
Turn around and look at the building diagonally across the street.

Brown Proctoria Hotel.

This splendid hotel building, once the pride of Winchester, is the lineal descendant of hotels that have occupied the same site for 112 years.

In 1804 Mr. Flanagan built a log rooming house, which was the first “tavern” in the town and became known as the Flanagan House. On July 4, 1805, there was a notable gathering at the tavern to hear Henry Clay speak from the stump of a large bur oak tree.

Around 1824, the Flanagan House was replaced by a brick structure that was thought to be one of the first brick hotels in the state until its demolition in 1904 to make room for the present day Brown Proctoria. The brick hotel, originally known as the Old National House, was later renamed the Reese House after Major W.E. Reese purchased the land.

The lower portion of the building adjacent to the Brown Proctoria on Lexington Avenue is believed to be part of the original structure of the Reese House that was used as hotel rooms in the 1890’s. Two Presidents, Andrew Jackson and Jefferson Davis, are known to have stayed here.

The Brown Proctor, as it is commonly referred to, was the most preferred hotel in town in the early 1900’s as it was the farthest from the railroad. The walls are surfaced with Indiana limestone on the first floor and granite brick on the upper floors. It now serves as an apartment complex.

This is another building with a definite postcard view. We are not looking at close-up details so there is no reason to stand next to it.
Walk to the first light pole on your left. Turn to face the building on your right.

1880.

This broad, impressive commercial structure was built for Dr. Washington Miller, president of the Citizen’s National Bank. It was the home of Arctic, Turnbull and Co, a dry goods store with offices on the second floor.

The upper part of the facade is divided into three sections. The central section has a tall window with an “1880” date plaque set on a raised diamond pattern under the segmental arch.

Continue along the sidewalk. When you see a pedestrian crossing sign on your left, look at the building on your right. It will have a number 47 above the door.

Old Clark County National Bank.

This is the only remaining iron-front building in Winchester. It was completed in 1880, and the upper floors were rented as offices. It was once noted in the local newspaper as “the finest bank building in the state outside of Louisville...”
Continue walking along the sidewalk to the second storefront on your right.

Bloomfield Department Store

The Bloomfield Department Store was a Winchester institution from 1885 to the late 1980s. The segmental gable is covered with lowrelief swags. The two protruding bay windows are also decorated with swags.

If you let your eyes wander above the bay windows you will find a likeness of Vic Bloomfield, founder of the department store.

Walk to face the courthouse building on the opposite side of Main Street.

Courthouse 2.

The original courthouse was a two-story, four-room log cabin built in 1794 at the cost of $16. Previous courthouses stood on this spot and were constructed in 1797 and 1822 with the present building constructed in 1853.

It is said that Henry Clay made his debut as an attorney at the Clark County Courthouse as well as his final appearance in court. The Courthouse clock was installed in 1907. The caretaker had to climb into the loft once a week to scare off pigeons roosting on the wooden minute hand. The weight of these pigeons caused the clock to be 15 minutes late. This problem was eventually solved when an electric device was installed to “wind” the clock.

The Courthouse was placed on the National Register of Historic places in 1974.

Now we can cover the building-specific bits with a better view.
Continue walking to the corner and cross to the opposite side of Broadway Street. Turn left to look at the Kerr building across the street. Look up.

Kerr Building 2.

The origin of the rooster perched high above the building is found in the tale of two local businessmen with unwavering political beliefs. In 1932, Franklin D. Roosevelt was running for president against the incumbent Herbert Hoover. Winchester businessman N. Rol Ratliff, a staunch Democrat, made a friendly wager with Ogden Estes, who was a dyed-in-the-wool Republican. They bet on the outcome of the election, each supporting his party.

Money being short, the terms were as follows: If Hoover won, Ratliff had to push a peanut up Main Street with his nose. If Roosevelt won, Estes had to stand on top of the Kerr Building, flap his wings and crow. A large crowd gathered to watch Estes pay off his bet. John McLeod, father-in-law of Francis Ratliff and woodworker by hobby, furnished a rooster for the occasion. The wooden fowl was installed and stood atop the building for over fifty years. A few years later the famous rooster disappeared.

(Enoch, Harry; A History of the S.P. Kerr Business Block and the Eclipse Mills)

The best view of the building is from the previous corner but the rooster is best viewed from this corner.
Turn around and walk down Broadway Street. Look for a door on your left with a 17 on it.

17 East Broadway.

This is the birthplace of Helen Thomas, the recently retired United Press White House correspondent. At the President’s press conferences, Ms. Thomas and the AP White House Chief alternated the honor of asking the first question and closing with a “Thank you, Mr. President.” She was one of nine children of Lebanese immigrants. After working her way through Wayne State University, her first newspaper job was as a copy girl at $17 a week.

You are done! 








Turn around and walk back to the intersection. Turn right and continue walking until you see the parking lot on your right. You are back where you started.














Winchester, Kentucky





The City of Winchester was created in 1793 from 66 acres of land donated by a frontiersman named John Baker who owned 319 acres. It was a wilderness, a farm of cane-covered hills, and its one advantage was a spring large enough to provide water for 500-600 people. He broke the land into lots, laid out streets, and provided free land to the county for a courthouse, a school, a jail, and a stray animal pen. The town was named in honor of Winchester, Virginia, Baker’s former home.


By 1797 Winchester consisted of 11 homes connected by a series of paths through the cane. The streets were laid out but not completely cleared, and there were stumps in the middle of Main Street until 1800. By 1800 there were 20 stores, six taverns, 10 churches, six lawyers and one doctor.


In 1812 Winchester was listed as the seventh largest town in Kentucky. It was a thriving town of 412 people and boardwalks were built to permit crossing muddy streets. There was little organized education in the first years, but in 1810 a school was built at the corner of Hickman and Highland and continued at that site until 1974. The Winchester Downtown Commercial District was placed on the National Register of Historic Places in 1982.


Winchester’s Main Street is known to locals as the “White Way” because of the five-globed lampposts that were originally gas-burning lights. The name comes from Eastern Kentucky poet and author Jesse Stuart’s poem “Up Silver Stairs,” in which he expresses his reaction to seeing the lights while flying over Winchester one night. The lamps were installed in 1912 and were removed in the mid-1950s in favor of brighter lights. In 1983, 10,000 people gathered in Winchester to celebrate the relighting and rebirth of the White Way with two of the original fixtures and many replicas.


Main Street was a dirt pathway until the City Council, in 1910, accepted the plea to cover it with bricks. During the 19th Century, an electric streetcar traveled from Depot Street to Moundale Avenue and was pushed around manually to make its return journey. At the end of the day, the driver would go into a store, call the electric company and have them turn off the power to the streetcar.


Winchester has one of the few elevated sidewalks in the Commonwealth of Kentucky giving this block of Main Street the name “High On Main.”












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