The Windsor Family


Few other families have had more of an impact on the formation of downtown Milford than the Windsor Family. As owners of the Dorsey, Norman and New Windsor Hotels, the Windsor’s provided many travelers with lodging after long train rides. However, the Windsor’s were also well known for their interesting outlook on life, their love of nature and their rough-and-tumble ways.

Thomas Windsor arrived in Milford in 1894 after operating a general store in the Gumboro area for many years. He was married to Elizabeth Wootten Windsor and the couple had eight children, Harry, Lelia, J. Edward, T. Thaddeus, Charles, Frederick, Norman and Ruth. Thomas was sheriff of Sussex County during the Collingwood P. Hallett case when Hallett was convicted of the murder of James Deputy. Hallett was sentenced to hang, but escaped and was never captured. Soon after the trial, Thomas relocated to Milford.

According to Milford Historian, Dave Kenton, Thomas purchased a home at the northeast corner of Southeast Front Street and Pearl Alley, behind the hotel he purchased from the heirs of W.N.W. Dorsey. The home was the second oldest home in south Milford with only the Causey Mansion dating further back. It was built in 1811 by Henry Hudson, one of the founders of Milford. The home was demolished in 1964 after Lelia Windsor Jennings, the last of the family, passed away.

Thomas operated the Windsor Hotel, which was formerly the Dorsey Hotel, until his death, a death that was one of the most famous in the city. Thomas was a fair and understanding father but also took great care of his horses. His son, Edward, requested to use the horses and carriage in order to transport revelers to and from Slaughter Beach during the Independence Day celebration of 1901. His father agreed, but since Edward was known to have a taste for alcohol and was unmanageable when drinking, Thomas told him he could only use the horses and carriage if he were sober.

When Edward arrived on the morning of July 4, 1901, he was in poor condition as he had been drinking heavily the night before. Thomas refused to allow him to take the team, leading to an altercation in the hotel’s saloon. Edward left and returned with a shotgun, firing a shell into his father’s stomach. Thomas did not die immediately, despite being shot in the left chest. He called for an attorney as he lay on his deathbed and disowned Edward. Thomas died at the age of 54 at 7 PM on July 5. The sheriff arrived to arrest Edward, but the family convinced him to allow the young man to attend his father’s funeral the following day.

In an account from Charles Windsor as told to Francis Wootten, family members were sympathetic to Edward’s plight. They loaned him money and helped him flee Milford in a wagon covered with hay or straw. All money was repaid to the family and Edward was never captured. A letter written by Marjorie Poore and archived in the Milford Museum relates a story she heard from her husband, Herschel. The letter was written to Catherin Holcomb and tells the tale of George Hobbs who lived next door to Mr. Poore’s father’s grocery store. Mr. Hobbs was in the service and fought in the Spanish American War.

According to Ms. Poore in 1992, Mr. Hobbs was stationed at a base near San Francisco and often went into the city when on leave. At one of these times, he met Ed Windsor on the street and they stopped to talk. They eventually went to a bar or restaurant to continue the conversation. Mr. Hobbs had to get back to base so they made plans to meet again at the same place the following Friday night. Between the first meeting and the next that was planned, the 1906 San Francisco earthquake occurred and Mr. Hobbs could not get back to their meeting place.

“When Mr. Hobbs was able to get back to the meeting place, he could not find Mr. Windsor anywhere,” Ms. Poore wrote. “For many leaves or passes to come, he went back to the same place and walked around and asked questions but never again saw or heard from Ed Windsor. This lead him to believe he was lost in the earthquake.”

Harry Windsor, the oldest son, took over the hotel and restaurant after his father’s death. During that time, liquor was served with what was known as a “local option,” which meant liquor may be available after one election but not after another. In Milford, liquor was available until the national prohibition from 1920 until 1933. During times when liquor was not permitted, the saloon, which later became known as the “Zoo Bar,” became a newsstand and soda fountain. There was a billiard parlor in the rear of the building for many years.

Eventually, Thad Windsor, the younger brother of Harry, purchased the Central Hotel on Front Street, renaming it the New Windsor Hotel. He renovated the hotel extensively and became one of Milford’s most memorable characters. Behind the hotel, he kept wild animals including bears, wolves, birds and monkeys. He was an avid sportsman and hunter, taking safaris to hunt big game. Many of the stuffed animals displayed in the saloon were those that he hunted, although some may have been donated by his friends. The animals included a mountain lion, buffalo, polar bear, moose, hawks and a tuna fish.

Harry Windsor died in an automobile accident while traveling with Thad in West Chester, Pennsylvania. A car overturned on Harry and, although Thad was able to remove the vehicle, a fellow passenger was too frightened to pull Harry from the wreckage and he succumbed to his injuries.

Thad loved to hunt and enjoyed living among wild animals. However, he soon found that sleeping in the swamp could be uncomfortable. He bought a used Model-T stake body truck and had local millworks create a small house that was attached to the flatbed of the truck. A door in the back allowed entrance and there was a small coal stove, table and two bunks. Windows on each side allowed light in during the day and a lantern provided light at night. It is believed that this was the first recreational vehicle in Sussex County.

Norman Windsor, another brother, purchased the Dorsey building from his brothers and sisters. He leased the soda fountain and newsstand from 1925 to 1935 to two men from New York who were known as Cohen and Levi. When prohibition ended, Norman saw the potential for profit in a bar and hotel, so when Cohen and Levi’s lease expired, he built a new hotel just south of the old Dorsey building. He called the new hotel the Norman Hotel and ran it along with the bar in the Dorsey building until he died in 1942. Apartments and rooms were rented on the second floor with various commercial businesses renting the first floor.

The Norman Hotel and Dorsey Building remained the property of the Windsor family until it was sold in 1981 to Daniel V. and Ruth Sizemore. The Dorsey Building was demolished in 1992 in order to create the Riverwalk. The Norman Hotel now houses businesses on the first floor and apartments on the second. The New Windsor Hotel houses office buildings after extensive renovations in 1999.

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