The Windsor Family

The Windsor Hotel stands on Northwest Front Street, as stately as it was when it was constructed in 1892 as the Central Hotel, following a fire that nearly destroyed downtown Milford. However, this was not the first Windsor Hotel to serve Milford visitors, and both of these locations are named for the Windsor family, who has a colorful and interesting history in Milford.

Thomas Windsor, born August 6, 1849, arrived in Milford in 1894 from Gumboro where he had operated a general store. He was the son of Captain John Windsor and Nancy Cannon. He joined an older brother, John Cannon Windsor, born in 1887. His wife, Mariah Elizabeth “Lizzie” Wooten Windsor, born June 1, 1853, was the daughter of Isaac James and Elizabeth Caroline Gray Wooten.

The couple had nine children. Harry B. was born August 19, 1872; Lelia Kyle was born January 14, 1874; James John Edward wasw born in September 1876 Genevieve “Jennie” was born July 1878; Thomas Thaddeus was born July 31, 1880; Charles Cullen was born March 15, 1883; Frederick C. was born August 1885; Norman L. was born September 19, 1889, and Ruth Dorsey was born November 22, 1889.

The Windsor family made their home at the corner of Northeast Front Street and Pearl Alley; behind the hotel he purchased from the heirs of William Nicholas Washington Dorsey on South Walnut Street. Other than the Causey Mansion and the original section of the Parson Thorne Mansion, the Windsor home was the oldest in Milford, built in 1811 by Henry Hudson, one of the founders of Milford.

The Windsor children were a rough-and tumble group, described as high-living, hard-drinking, self-reliant country folk. The Windsor boys were not bound by social and religious convention like most of Milford’s society at the time. Arriving here from Gumboro, which at the time was a rural, agricultural community, with no family roots to temper their behavior, the boys were known for their socializing, dancing and drinking lifestyle. The rough-and-tumble lifestyle, however, led to tragedy.

On July 3, 1901, J. Edward asked his father if he could borrow the family carriage and team of horses to celebrate July 4^th at Slaughter Beach with friends. Thomas told his son he could have the carriage as long as he was sober and prepared to be responsible for the horses. When J. Edward arrived the next day, however, he was not sober and his father refused to allow him to take the team. There was an altercation in the hotel saloon. J. Edward left and returned with a shotgun, shooting his father in the stomach.

Thomas called for an attorney and revised his will, eliminating his son from the estate and died soon after. When the sheriff arrived to arrest J. Edward, he was persuaded to allow the young man to attend his father’s funeral the following day. According to Charles, J. Edward’s younger brother, family members were sympathetic to J. Edward and loaned him money to flee. He was smuggled out of town in a wagon covered with hay.

A newspaper account a few months after the murder indicated that a body found in Ellendale Forest was that of J. Edward. However, George Hobbs who knew J. Edward claims it was not. Hobbs was in the service and stationed near San Francisco where he told friends and family, he ran into J. Edward on the street in 1906. The men went to a bar and restaurant where they caught up and when it began getting late, Hobbs had to get back to his base. The men made plans to get together again the next Friday night. The San Francisco earthquake struck between the two meetings. Hobbs could not locate J. Edward again after that and he believed he died during the earthquake.

The oldest son, Harry, assumed responsibility for the hotel and restaurant. During the early 1900s, liquor was handled by what was known as “local option,” which meant liquor in the town might be permitted one year and not the next until national prohibition halted liquor sales from 1920 until 1933. During the years liquor was prohibited, Harry operated a newsstand and soda fountain in what eventually became the Zoo Bar in later years. A billiard parlor was established behind the soda fountain, and it is highly likely bootleg liquor was served in the billiard parlor.

At the time, the Central Hotel stood on Northwest Front Street. Originally constructed by Maritinius de Waele, an immigrant from France, the hotel was a frame structure originally. The first structure was built around 1811. When de Waele died intestate, the hotel descended to his widow, Joanna, who leased it to Jabez Collins Shockley who later married Regina de Waele, the daughter of Joanna and Martinius. At that time, the hotel was known as the Union Hotel.

The hotel was operated under various owners after the death of Regina and Jabez until Kramlich took it over in the early 1880s. It was Kramlich who changed the name to the Central Hotel. He also improved the exterior with the addition of a four-story brick addition while parts of the older section of the hotel remained on the western side.

A fire in downtown Milford on January 28, 1891, burned the stable and icehouse of the hotel. It also damaged wooden portions of the building. Kramlich rebuilt the damaged portions, adding a wrought iron railing and sidewalk canopy. This time, the entire building was constructed of brick. An advertisement in a local paper provided details on the upgrades.

“New furniture, new house, new management, the house lighted throughout by electric light and heated by hot water.”

Electric was relatively new to Milford so the fact that the hotel offered electricity was newsworthy. In 1910, the Milford Emergency Hospital was located on the top floor in the ballroom after moving from the Masonic Building. This was a temporary solution as the hospital moved by 1913 in the Marshall building.

The Central Hotel was in competition with two other hotels in Milford. The Windsor Hotel on South Walnut Street as well as the National Hotel, located where Penny Square stands today. When the Windsor’s arrived in town, the National Hotel was owned by Justus Lowery, the brother-in-law of Governor Peter Causey, who was also a colorful local character.

After the death of his father, Thaddeus, who was known as Thad, ventured out in a business of his own, purchasing the Central Hotel on Northwest Front Street and renaming it “The New Windsor Hotel.” Thad was one of Milford’s most notorious characters, despite being an astute businessman. He kept wild animals in cages at the rear of the hotel, including bears, wolves, birds and monkeys. There was also a raccoon named Steve that was well-known to Milford residents.

A 1905 article in the Morning News reported that “Jocko, who is probably the most noted monkey in this state was yesterday placed in the Wilmington Free Zoo, a gift of Thaddeus T. Windsor of the Windsor Hotel in Milford.” The paper continued stating that the monkey was of the “baboon species” and brought to this country by a ship captain and eventually given to Thad. Accounts in other papers claim that the monkey “appeared to be vicious and snapped at everything placed within reach of his paws. He is strong and at times rocked his cage, a large crate, with great violence.”

Newspaper accounts of the day were filled with reports of Thad’s wildlife conquests. In 1909, the Evening Journal reported Thad caught a large sea turtle at Bowers Beach weighing about 50 pounds. When it was brought to Milford, it “attracted considerable attention.” Another in 1904 reported that Thad and his hunting friends had “great luck” in Rehoboth, “bagging 26 rabbits, five squirrels, one raccoon, six quail and one hawk.”

Not only were there live wild animals behind the hotel, but Thad’s hotel also reflected his own lifestyle. The dining room often offered wild game and waterfowl which he had personally bagged during his hunting excursions.

An avid hunter and sportsman, Thad took many safaris to western areas of the country to hunt big game. Many of the animals he hunted were preserved and displayed in the saloon operated by his brother. This led to the name “The Zoo Bar” and a preserved mountain lion is now on display at the Milford Museum.

Adored by the younger population in Milford, Thad was a fixture in local theater events and led parades on a beautiful palomino horse. He loved the limelight and made sure his hotel was the center of many social events. At that time, high society in Milford existed in the northern part of town and the New Windsor Hotel was the focal point for that society from 1914 to 1950.

With the railroad bringing visitors to Milford, the New Windsor thrived. Salesmen and visitors met the hotel hack at the railroad depot and were transported for free to the hotel. There, they were greeted with a freshly prepared meal, great entertainment and a bar that was second to none. In the evening, guests would sit on a raised platform front porch protected from rain where old-timers told stories and swapped local news. Salesmen displayed their products in a rear section called the sample room.

There was still steamboat service in Milford even after the arrival of the train, but rail travel was more convenient. As many as seven trains came and left Milford daily while steamboats made only one trip to and from Milford based on high tide. When the Coleman duPont Highway, now Route 113, was completed, more visitors arrived by automobile than train.

In December 1921, Thad and his brother, Harry, were involved in an accident in West Chester, Pennsylvania. The car they were in overturned, pinning Harry underneath. Although Thad was able to move the car off of Harry, another passenger was too frightened to move him, and he died of his injuries.

Harry and Thad’s younger brother, Norman, purchased the original Windsor Hotel from his siblings and became sole proprietor. The soda fountain was leased to two men from New York, Cohen & Levi, but once prohibition ended, Norman saw potential in the bar business. When the soda fountain lease ended, Norman built a new brick hotel just south of the current one, naming it the Norman Hotel.

Thad married Mary Hall and had a son Thad Theodore “Ted” Windsor. Thad died in 1950 and the hotel was purchased by Seymour Gellens and his wife, Lillian, who renamed it the Milford Hotel. The Gellens’ focused on the dining room. They also opened a package store in the west wing while rooms were rented on the upper floors.

Lelia, the oldest Windsor daughter, married William H. Jenning on April 30,1912. At one time, the couple lived in Cedar Creek, although most of their marriage was spent in Milford She died July 21, 1966. Jennie, the second sister, married Oliver Fearing Gilbert although the date of their marriage is unknown. They moved to North Carolina where they had two children, Mary M. in 1906 and Oliver F. in 1909. Jennie died in 1946.

Charles married Stella D. Sharp in 1917. It appears the couple had no children. He died November 7, 1971. Frederick died January 27, 1929, at the age of 44 and there is no indication he ever married. Norman never married and died March 26, 1942, at the age of 53. The youngest sibling, Ruth, never married and died on June 6, 1977. She remained in the Windsor home until her death. The home was demolished to build the new library.

The New Windsor Hotel was sold in 1967 after the death of Seymour to Thomas Hanley and Orville Shockley. The new owners added a new bar area and dance floor. Upper floors were rooms rented to low-income tenants who were often transient. Very little maintenance was done to the upper floors, and it began to deteriorate.

Gene and Jeanie Fitzgerald purchased the hotel in 1974, but the upper floors were, by then, unusable. They operated the bar and package store as the Kent and Sussex Inn for many years. They did renovate a few of the rooms for use as a hotel.

In 1996, Riverbank Associates has purchased the Jump Block on Walnut Street and built a new office building. There was a need for additional parking, so the group purchased the Kent and Sussex Inn from the Fitzgerald family. Riverbank Associates invested a considerable amount in the building, completely renovating the interior.

On August 20, 1999, the New Windsor was rededicated at a gala celebration. Today, the building houses State of Delaware and other offices. The lobby and staircase still provide insight into when the hotel was the place to stay in Milford. Today, the hotel is noted on the National Registry of Historic Places.