A walking tour of the old red light district in Hudson, New York

Fifteen years ago Bruce Edward Hall published Diamond Street: Hudson New York; The Story of the Little Town with the Big Red Light District, a very entertaining description of the lurid underside of Hudson’s long history.

The Quaker Meeting House on Union Street

The Quaker settlers who founded Hudson in 1783 were seeking a port for their whaling vessels that was far enough inland to escape the harassment they had experienced on Nantucket from the British navy during the Revolution. Hall speculates that the “brazen harlots” who had been recruited to entertain British troops found their way to the new port of Hudson after the victorious Americans kicked them out of New York City that same year. Whether this legend is true or not, there is no question that Hudson’s reputation as a center for vice began just after the Revolution and continued until state troopers led a huge raid on the local brothels in 1950.

Sadly, Bruce Edward Hall died in 2003 at the early age of 49. The walking tour included in his book, which he calls “The Hudson Red Light Walking Tour; A Self-guided Lowlife Adventure,” is based on his observations of the town in 1994, and much has changed in the ensuing fifteen years. We decided to follow the exact route set by Mr. Hall, to photograph the scenes of so much mischief and mayhem, and to accompany the photos with some choice quotes from Bruce Edward Hall.

The Hudson Opera House

Our first stop was the Hudson Opera, which has been thriving since 1992 as the venue for over a thousand performances of all kinds. From 1873 to 1962 the city police station was on the left side of the ground floor. The Hudson municipal offices were on the right side. Doubtless, many envelopes of illicit cash were exchanged on these premises.

Hudson Opera House theater

The upstairs auditorium was the scene for everything from political rallies to vaudeville shows. Funds are currently being raised to complete renovations of the theater space.

Site of the Lincoln Hotel

Turning left from the front door of the Opera House, we came to an empty parking lot where the Lincoln Hotel once stood. Long ago, a recovering prostitute threatened to throw herself from the roof to avoid testifying against her highly placed clients.

Where Mrs. Benson warned her granddaughters

Across the street is an old mansion at 306 Warren, where Mrs. Benson forbade her granddaughters from sitting at the windows, lest they be mistaken for ladies of easy virtue.

Upper Warren, where the well-to-do lived

Only a block from the red light district, this part of Warren (then Main) Street was home to the wealthiest of Hudson’s citizens.

Site of the General Worth Hotel

The Hudson Electric Supply, at 217 Warren, now occupies the site of the old General Worth Hotel. According to Hall, “for most of its history, bellboys and waiters were on various Madams’ payrolls, receiving a cut for every customer they steered in the right direction."

The Tainted Lady Lounge?

Across the street from the hotel, where there is now an empty lot, “the Tainted Lady Lounge touted Hudson’s old reputation until the 1980s."

Where Legs Diamond's bodyguards kept watch

In what is now an empty lot at 248 Warren, Mike Finn ran a barbershop in the 1930s. “Whenever Legs Diamond came here to get his hair cut, Mr. Finn would pull the shades down while Mr. Diamond’s henchmen stood outside, carrying their tommyguns in violin cases.”

Allen Street, where the middle class lived

Following Hall’s directions, we turned left on Second Street and walked two blocks to Allen. “This was a solid middle-class neighborhood in 1875, when most people who resided here could expect to live at least into their sixties. The same year in Hudson’s poorest neighborhood (the corresponding blocks on the opposite side of Warren Street, the average age of death was nineteen.” We could not help but wonder about the mortality rates among Hudson's poorest and wealthiest residents in our own time.

52 Front Street, once the Langlois Saloon

Following Allen Street downhill to Front Street, we came to 52 Front “once painted bright purple as the home of the Langlois Saloon. Inside, the slovenly women at the bar provided very cheap thrills for those on a budget.” The building is now vacant, except perhaps for a few slovenly ghosts.

Half Moon Bar on the site of the Curtis Hotel

On the other corner of Allen and Front, where the Half Moon Bar now stands, was “the infamous Curtis Hotel, a house of assignation where philandering couples could go, no questions asked. It burned down in 1931.”

The port of Hudson, where seagoing vessels docked

Across Front Street is an old bridge leading over the Amtrak line to what remains of the once proud seaport of Hudson, now a marina for small craft. As late as the 1930s, dayliners carried travelers to New York from this point.

The Promenade, where Hudsonians showed off their finery

The Promenade, a public park originally called Parade Hill, was given to the city by the Quaker proprietors in 1795, and rose fifty feet above the busy seaport where whaling vessels and other seagoing craft docked. According to Hall, "Parade Hill, with its beautiful view of the river, provided the rich or the merely pretentious a place to walk in public and show off their finery."

Saloon of the notorious desperado, John Kiere

Hall tells us that the large three story building on the corner of Front and Warren was the saloon of the notorious desperado John Kiere in 1876. That was the year Kiere was again involved in a shooting as he had been in the famous shoot-out of 1869 at the Central House Hotel at Warren and 5th Streets.

In 1876 this was Hudson's largest brothel

At the corner of Front and Partition Streets, Mary Mackey operated the town's largest brothel of the 1870s. The building, formerly occupied by Maxie's Urban Bistro, is now vacant.

Vinegar Hill today, once "a hangout for disreputables of both sexes"

Continuing four more blocks on Front brought us to a narrow unmarked alleyway that is officially listed as Prison Lane. Across from Prison Lane, the knoll where the original log jail stood was later known as Vinegar Hill, “a mid-nineteenth century hangout for disreputables of both sexes.” The Hudson Terrace Apartment Houses now occupy the site. It was here I happened to witness my first drive-by shooting a couple years ago on the way home from the train station.

Kiere's bordello on right, Larry Mack's saloon on left

Walking back up Warren Street, we followed Hall’s route and turned left on Second Street. Just past Prison Alley on Second Street yet another brothel flourished, this one owned by none other than John Kiere. “A murder on its steps once precipitated one of the biggest sensations of the 1800s," according to Hall. "In the brick building next door was Larry Mack’s saloon, where the body was taken and a mob formed to lynch the alleged murderers – or was it a murderess?”

The murder grew out of an drunken attempt by a young man to rescue his wife from a life of sin and shame. Annie Spaulding, a married woman of fifteen, had left her husband Giles one winter day in 1876 and walked two blocks down Diamond Street to start a new life in the house of ill fame run by John Kiere’s devoted wife Ellanora. Giles was not happy with this turn of events but was unwilling to risk facing Kiere. Waiting until the saloon keeper took Ellanora off for a trip to New York, Giles recruited a friend, Charles Hermance, and after a few drinks to fortify themselves, they set off together for the house of infamy. Their first efforts being rebuffed by the ladies at the house, the two had a few more drinks before returning to rescue Annie.

Did Annie Spaulding watch the murder from
this balcony at Kiere's bordello?

This time John Kiere was at the bordello and greeted the would-be rescuers with a loaded revolver. He fired and Hermance fell dead. Ellanora went promptly to the police station to turn herself in for the crime. The jury, however, did not buy the story that she, and not her husband, was the killer and convicted Kiere of murder. He was sentenced for life to Dannemora prison.

Tidy houses on the 200 block of Diamond Street

Turning right, we walked along the once infamous 200 block of Diamond Street (renamed Columbia Street in the 1930s) Originally, the location for a sperm oil works for the whaling industry, this block hosted dozens of small brothels over a period of 150 years. The editor of the 2005 edition of Hall’s book warns that most of the Diamond Street sites described by Hall in 1994 have been demolished. We found several tidy new houses, many empty lots and a few older buildings.

Where lives were ruined by Hudson's
infamous floating crap game

An empty lot on this block is most probably the location of the garage described by Hall as the last home of "the high-stakes floating crap game that netted some $70,000 per month and was responsible for destroyed lives and ruined careers up and down the Hudson River.”

Boarded up bordellos on the 300 block of Diamond Street?

Who can say what this ancient staircase
on the 300 block has seen?

Between Third and Fourth Streets was the most notorious section of the red light district, known simply as “The Block.” Hall reports that almost every old dwelling on this block was a bawdy house at some point between 1800 and 1950, when Governor Tom Dewey initiated a massive raid by state troopers that brought an end to an era. The addresses occupied by some of the most colorful characters, such as #325 where Kate Best ran a bordello during the Civil War, are now empty lots.

The Mansion House, biggest brothel
of the 1930s, once stood here

A parking lot is all that remains of the Mansion House, at 330-334 Columbia (Diamond) Street, the biggest brothel of the 1930s. “Its ladies were famous for their versatility and the drinks cost a whopping one dollar."

#350 & 352, where Ma Brown and
Mae Gordon kept brothels

Columbia County Human Services
now occupies much of the old "Block"

A few of the old houses described by Hall in 1994 are still standing, including #350 where Ma Brown kept a brothel with its own small bar/restaurant and #352 where Mae Gordon maintained an establishment. Mae was one of the last madams in town and was arrested in the big raid of 1950. Later on, she went to live with her daughter in Albany.

The former insane asylum viewed across
the site of the old high school

The Hudson City Library, formerly an insane asylum and orphanage, can be seen across the empty field where the high school once stood. “When there was a fire on the Block one early-1930s afternoon, students in the science lab rushed to the windows, gleefully picking out familiar faces among the half-dressed johns fleeing the flames out the brothels’ rear windows.”

4th & Warren, once a favorite gathering place
for idlers and troublemakers

Turning right on Fourth Street, we came to the corner of Warren, “an intersection known in the nineteenth century as Central Square. It was a favorite gathering place for idlers and troublemakers, with a plethora of saloons in the surrounding blocks.”

Location of Macabees speakeasy

Diagonally across is 401 Warren. On the second floor of this building was “Macabees Hall, a popular speakeasy. With the repeal of Prohibition, Macabees was closed and forgotten.” Hall tells of the 70-year-old graffiti and the classic peephole in 1994, but the editor of his 2005 edition says that the interior has been much changed in the intervening years.

A woman was hanged here in 1817

Turning right on Warren, we passed the home of the Register-Star. “It was built in 1800 as a replacement for the old log jail, and was then located just beyond the edge of town. In 1817 its front yard was the scene of a public hanging of a woman for the murder of a child.”


As we return to the Opera House, Hall invites us to “imagine yourself as one of the hundreds of people jeering and catcalling at the johns, girls and gamblers hauled in by the truckload one steamy summer night nearly forty-five (now fifty-eight) years ago, ending an era many view with nostalgia.”

Nostalgia aside, Hudson remains the same small city where the well-to-do coexisted uneasily for two centuries with a poorer and more desperate underclass, and many middle class folks lived their lives without much contact with either.