Longwood Inn

300 North Ronald Reagan Boulevard

Longwood founder Edward Warren Henck commissioned Josiah B. Clouser to construct the hotel in 1883. This was Henck’s second hotel in Longwood, having just completed the first (“Original Longwood Hotel”) on East Warren Avenue earlier that year.

This large frame Vernacular-style building was mainly completed in 1885. Orlando realtor John Sinclair listed it for sale that year at a price that was a “large sacrifice.” Sinclair represented that it could be completed within 30 days.

It was purchased by Carlos Cushing, who finished the construction in 1886. Cushing named it “The Waltham,” after a district in Boston. Cushing lived on the south side of Lake Brantley in what is now Altamonte Springs, and his wife was responsible for the construction of the Lake Brantley Union Chapel.

In a flyer published by Henck in 1887 promoting Longwood, he described The Waltham as follows:

“This new house is furnished with all the improvements of a first-class hotel, having electric bells and bathrooms, is nicely furnished, and can offer to tourists and invalids all the comforts of a winter home. It is situated at the junction of two railroads, forty-one hours from New York, by Pullman cars. Longwood is an incorporated town eight miles from Sanford, amid young and bearing orange groves. It has five churches and two schools, a post office, a depot, and a telegraph office within a three-minute walk of the hotel. A large store filled with an excellent stock of goods. The sportsman will find the best of hunting and fishing in the vicinity. The proprietor’s long experience in conducting homes at Rye Beach, New Hampshire, is a guarantee that this hotel, while under their management, will run for the comfort and pleasure of its patrons. Open Jan. 3, 1888. Terms $3.00 per day, with a reasonable reduction to permanent guests.”

Like many Florida hotels at the time, it was only open during the winter season. The hotel proprietors engaged in the common practice of “pairing,” where they worked in cooperation with a New England resort that operated during the summer months. The managers alternated between the two resorts during the two ends of the year.

The hotel entertained numerous visitors, who enjoyed the excellent hunting and fishing along the Wekiwa River. The Waltham was a haven for winter tourists and a center of local activity, attracting lumbermen, cowboys, farmers, and townsfolk.

The hotel was shuttered for many years after the devastating freezes on December 26, 1894, and February 7, 1895. After the Great Freeze wiped out groves, many area residents moved away, and visitors dried up. The hotel reopened as the “Longwood Hotel” in 1910 after it was purchased by Charles W. Entzminger, who refurbished it and added gaslights in the lobby.

George Clark bought the hotel from Entzminger in 1922 and renamed it the “St. George Hotel.” Clark was a successful shoe salesman for the Bass Shoe Company, and he also ran a girl’s camp in Maine during the summer. Clark rejuvenated the hotel and brought a lot of excitement for the town’s prospects at the dawn of the Great Florida Land Book.

On April 3, 1923, the Clarks invited the whole town for an ice cream social to celebrate the end of a booming tourist season. During the festivities, George’s wife noticed he was missing. She went searching for him and found him at the rear of the hotel, where he had fallen in an accident. George tripped over a rug and hit his head forcibly on the floor. He died in his quarters at the hotel the following day.

After George’s death, his brother Fred Clark took over the management and renamed it the Orange and Black Hotel. Fred promoted it with sportsmen, and it became well-known. It was also said that “bootleg whiskey, gambling, and painted ladies were all popular and available at the Inn. (1)”

In April 1924, the hotel hosted the governors of thirty-two states in a brief stopover on their way to the National Governors’ Conference.

In 1926, Ed Crocker, head of a syndicate that included baseball great Joe Tinker, purchased the building and renamed it back to the “Longwood Hotel.”

With the depression in the 1930s, the Longwood Hotel went into decline, and Florence Bunker Clark regained title to the property. In February 1947, Mrs. Clark sold the hotel to F. S. Saunders, and in a short time, it was resold to Maximillian Shepard, a restaurateur. Shepard waged an impressive publicity campaign and attracted several conventions, including the United Federalist Convention of 200 people. The Longwood Hotel restaurant was famous all over Central Florida for its cole slaw and Southern cooking.

George Barr, a well-known National League umpire for 19 years, conducted the George Barr Umpire School at the hotel from 1952 to 1957.

Maximillian Shepard sold the hotel at auction to Louis T. Hunt in 1957. The hotel had special meaning to Hunt and his wife, Bobbi Jo (Allen) Hunt, who had been previously married at a ceremony there. Bobbi Jo was the daughter of the grocery just across Church Avenue. The Hunts managed the restaurant and lived in an apartment on the second floor. When Bobbi Jo died, the ownership went to her son Louis Hunt Jr., who ran the hotel as a low-rent boarding house for migrants.

In late 1964, the hotel (and surrounding parts of the town) was filled with film crews and movie stars. A feature movie initially called “The Cry of the Laughing Owl” (later renamed “Johnny Tiger”) was shot here. It starred Robert Taylor, Chad Everett, and Linda Scott and debuted in theaters in 1966.

In the fall of 1972, Mrs. Robert S. Bradford (a founding member of the Longwood Historic Society) bought the hotel, formed a corporation with her son and daughter-in-law, and changed the name to the “Longwood Village Inn.” She was instrumental in having the Florida Bicentennial Committee dedicate the Longwood Village Inn as a Historical Landmark along the Bicentennial Trail on July 26, 1976, the first such site named in Florida.

The Bradfords began renovation work in November 1972 and had their grand opening party on January 2, 1973. The lobby of the Inn was decorated with Victorian antiques, and two dining rooms served as many as 300 meals a day. The inn hosted banquets, private parties, and wedding receptions. Two or three weddings took place each week on the stairs in the lobby. Florida Governor Rueben Askew was one of the many distinguished visitors to the Inn during the Bradfords’ brief ownership.

In 1973, Mr. and Mrs. George St. Laurent, Sr., of Closter, New Jersey, bought the hotel. Their daughter, Carrie, and son-in-law, Spyros Christoulatos, managed the restaurant and converted the second floor into offices. They redid the second dining room as a country-western bar and incorporated a Greek-style walkway to the parking area in the rear, replacing the old garden.

When Mr. St. Laurent, Sr., died, his wife donated the hotel to Cornell University in 1978. Both she and her husband had been students at Cornell. After receiving ownership, the University leased the hotel offices and restaurant to several managers.

Cornell University sold the Longwood Village Inn in 1983, and it was renovated as an office space.


The Longwood Hotel is significant for its Italianate design influences. These influences are exhibited in the window architraves, the central roof protrusion, and the heavy roof overhang support brackets. The heavy fascia provides a “hat” for the building, as Louis Sullivan advocated at that time in Chicago and St. Louis. The doubled central windows on each floor lead the eye from the magnanimous double entrance door to the apex of the pedimented roof protrusion. The arched beams connecting the six columns in the lobby open the room in an airy Italian atmosphere while supporting the heavy upper floors. The flanking stairways lend a touch of elegance, and the bulbous-turned newel posts and decorative balusters are another Italianate feature. This stairway winding around the central lobby is open to the third-floor ceiling, lending its shape to the chimney architecture and furthering the design’s openness.


1 – Interview: Hal Freeman by M. Ostrander, Longwood, Florida, 6 October 1983.


Longwood Village Inn Menu from the 1970s