In the early 1880s a Scottish investment group led by Sir John Gillespie purchased 60,000 acres from the Florida Land and Improvement Company, sight unseen. That must have been some sales brochure. Gillespie recruited sixty colonists, known as the Ormiston Colonists after his Scottish estate, to sail to the west coast of Florida. They arrived on Christmas Eve, 1885. What they found was land but no improvement; what Gillespie’s had purchased boasted one building and a trail. The Scots did not come unprepared, however. In their party was an architect, Alex Browning, to direct any construction necessary. The Scots platted out a street grid and named all the north-south streets running parallel to the water after fruits. Then they put the land up for sale.

That winter was a cold one, so cold it snowed. Most of the colonists left, they could get that back home.  When no land sold in 1886 and only eight lots in 1887, the directors of the Florida Mortgage and Investment Company ordered a voluntary liquidation of their holdings. Gillespie’s son, J. Hamilton, remained in Sarasota to see what could be made from his personal holdings. It was slow going. By the end of the century the families in Sarasota numbered about 15, fisherman mostly, and the streets were used primarily by cattle and swine. “Fleas,” it was noted, “outranked everything in population.”  

In 1902 Sarasota was incorporated as a town, and Gillespie was the first mayor. Municipal improvements included the paving of four miles of streets with two miles of cement sidewalks. By 1913 Sarasota was incorporated as a city as the population inched over 1,000. About that time Bertha Honore Palmer, widow of Chicago department store pioneer Potter Palmer, was lured to the area by an advertisement placed in a newspaper by A.B. Edwards, the first mayor after Sarasota became a city. Palmer declared Sarasota Bay every bit the equal of the Bay of Naples in southern Italy for beauty and raved about the sport fishing. Her comments were played up in the press and triggered the development of Sarasota as a resort destination. She purchased 90,000 acres in the area and with her sons developed an innovative cattle ranch.

Another pioneering resident was Alfred Ringling, one of the five Wisconsin brothers who established the famous Ringling Brothers Circus. The families of siblings Charles and John followed and not only were the Ringlings major players in the physical development of the city but they carried the Sarasota name around the world when they established the circus winter quarters here in 1919.

Our walking tour of Sarasota will begin in the historic center of town where just over 100 years ago John Hamilton Gillespie stood watching the cows and pigs and wondered if anyone was ever going to come... 

1.
Five Points
intersection of Main, Pineapple and Central streets

This intersection, where the right angle of the Sarasota street grid meets the curve of the bayfront streets has been the historic center of downtown since the first Scottish settlers built a boarding house here in 1885. Plans were hatched to build the town’s first skyscraper here but construction snafus delayed the seven-story First Bank and Trust Building enough that it became Sarasota’s second high-rise. The Neoclassical structure has been demolished and the Plaza at Five Points now stands in its place, looming over Sarasota’s most historic intersection.  

WALK EAST ON MAIN STREET, AWAY FROM SARASOTA BAY (THE PLAZA AT FIVE POINTS WILL BE ON YOUR LEFT AS YOU PASS).

2.
Kress Building
1442 Main Street

Samuel Kress founded S.H. Kress & Co. in 1896 and developed five-and-dime stores nationwide. An avid art collector, Kress took pride in creating beautiful buildings and heartily embraced the Art Deco style of the 1930s and $50,000 was spent to create this Egyptian-flavored Deco palace in 1932. Building ornamentation is executed in buff tile and glazed terra-cotta. Although the Kress stores are no longer, look up to the familiar “Kress” masthead in gilded letters. 

3.
Worth’s Block (The Gator Club)
1490 Main Street

This is one of the first brick commercial buildings to appear in Sarasota and the only one that shoppers from a century ago would recognize. William Worth migrated from Georgia in 1903 and purchased this corner at Lemon and Main. He constructed a wooden store that was adequate until 1912 when his ambitious 22-year old son, William “David,” bought the business and constructed this 100-foot deep two-story building. The first floor was occupied by the family grocery and the Worth family resided upstairs. Worth left in 1914 for business adventures that would take him to Savannah, back into the store for a bit, San Diego and back to Sarasota. The building was converted into the Gator Bar & Grille in the 1930 and after decades under suffocating metal sheathing was rehabilitated back to its original appearance when it became the Gator Club in 1988.

BEGIN WALKING EAST OF 1ST STREET, PAST THE FEDERAL BUILDING, WHICH WILL BE ON YOUR LEFT.

4.
Canandaigua National Trust
1586 Main Street

This two-story buff brick building began life as the headquarters of the First National Trust but the bank was doomed by the Depression. In 1931 the Kickliter Brothers Hardware and Paint Company movedinto the space. Today it is once again a bank and although the first floor looks like a hardware store look up to the Neoclassical styling of arched windows capped by keystones and corner brick pilasters that are topped with cast metal urns. Under the eave is a finely crafted frieze of decorative tile.

5.
First Baptist Church
1661 Main Street

This congregation organized in 1902 with five members. The first Sanctuary, now serving as a chapel, was dedicated December 14, 1924. Property immediately east of the church on Main Street was purchased in 1951 and the present Sanctuary cornerstone was laid May 29, 1962. 

6.
Links Plaza
Main Street and Links Avenue

Born in 1852 in Edinburgh, Scotsman J. Hamilton Gillespie inherited an heirloom set of golf clubs at the age of eight, and when he was sent by his father in 1886 to Sarasota to manage the floundering Florida Mortgage and Investment Company Gillespie was an interested in establishing golf as a new town. Soon after his arrival, he carved the land behind his home into a two-hole golf course. In 1905, while serving as mayor of Sarasota Gillespie laid out a nine-hole course at this location, one of a half-dozen he created in Florida. After Gillespie disposed of his Sarasota interests in 1910 he returned to Scotland to train soldiers for World War I. He came back to Sarasota and was on the golf course when he suffered a fatal heart attack in 1923. 

7.
The Crisp Building
1970 Main Street

This is one of the best surviving examples of Mediterranean Revival commercial architecture remaining in Sarasota from the 1920s. Thomas H. Crisp arrived in Sarasota in 1924 and this was one of his first projects, developing land purchased from Charles Ringling. Crisp’s vision helped stimulate the rise of the east end of Main Street into what the Sarasota Herald declared was the “finest and fastest growing development in the city.”

8.
Sarasota County Courthouse
2000 Main Street 

Sarasota County was carved from Manatee County in 1921 setting in motion plans for this home for the new county government. Land was donated by Charles and Edith Ringling and New York architect Dwight James Baum, who had just completed a mansion for John Ringling, was hired to design the courthouse. When he was up north Baum’s work tended towards the classical; in Florida his designs were almost exclusively Mediterranean Revival. here he created an H-shaped structure with a dramatic tower dominating the hyphen between the rectangular buildings. The courthouse is adorned with polychromed glazed terra cotta tiles and cast stone decorations; nationally known wrought iron artist Samuel Yellin created many of the elaborate grills and railings. Red barrel tiles for the roof were imported from Spain. After later additions to the courthouse covered the original facade along Ringling Boulevard you can only view the composition from the Main Street side.

RETRACE YOUR STEPS TO WASHINGTON BOULEVARD AND TURN LEFT. WALK ONE BLOCK TO RINGLING BOULEVARD. 

9.
Sarasota Terrace Hotel
101 South Washington Boulevard at Ringling Boulevard

Built by Charles Ringling in 1925 on the site of the number one green of the Old Gillespie Golf Course, this building was originally known as the Ringling Terrace Hotel. It later became known as the Sarasota Terrace Hotel. In 1962 it was purchased by Arthur Allyn to house the Chicago White Sox baseball team during spring training. The building was purchased by Sarasota County in 1972. After extensive remodeling, it is now the Sarasota County Administration Center.

TURN RIGHT ON RINGLING BOULEVARD.

10.
Charles Ringling Building
1924 Ringling Boulevard

When he wasn’t looking after his circus interests Charles Edward Ringling was investing in real estate and promoting the development of Sarasota where he established a residence in 1912. Here he purchased John Gillespie’s golf course to create a business section in what had formerly been a sandy wasteland. While architects Clas, Shepherd & Clas out of Milwaukee, Wisconsin were building him a million dollar mansion Ringling also had them draw up plans for this commercial property. For most of its life this stuccoed 1926 Mediterranean Revival building has housed restaurants and nightclubs.

TURN RIGHT ON ORANGE AVENUE.

11.
Federal Building
111 South Orange Avenue

Depression-era Works Projects Administration funds brought this Neoclassical post office to Sarasota in 1931. The symmetrically proportioned building, fronted by an octet of fluted Corinthian columns, was designed by New York architect George Albree Freeman. Then in his seventies, Freeman died a few years later and this is considered his last major work.

TURN LEFT ON STATE STREET. TURN RIGHT ON PINEAPPLE STREET.

12.
First Church
104 South Pineapple Avenue

The first church organized in Sarasota in October of 1891, meeting in a schoolhouse in Main Street when the circuit-riding preacher arrived in town. The church was formally organized with 12 charter members in a small building across from the current sanctuary. The congregation moved here in 1914 and settled into this Colonial Revival church on Christmas Day, 1955. 

CONTINUE ON PINEAPPLE STREET BACK TO FIVE CORNERS. TURN LEFT ON MAIN STREET. AFTER A HALF-BLOCK, TURN LEFT ON MIRA MAR COURT.

13. 
Roth Cigar Factory
30 Mira Mar Court

Tampa took the lead in cigar-making on Florida’s west coast but cigar-making in Sarasota blossomed in 1911 with the founding of the Saratoga Cigar Company by the Hill brothers, Jack and John. Within a short time the Hills were churning out 2,000 cigars a day but the company disappeared in 1916. Another set of brothers, Edward and Michael Roth, got into the game in 1917, rolling cigars at their newsstand on Main Street. In 1923 the Roths moved into this Spanish Mission building roll their 8-cent cigars. Sarasota’s cigar tradition ended when the Roths vacated the property in 1938.

TURN RIGHT DOWN THE ALLEY BESIDE THE ROTH CIGAR FACTORY. AT THE END OF THE ALLEY, ON YOUR LEFT IS...

14.
DeMarcay Hotel
27 South Palm Avenue

Scottish-born Andrew McAnsh ground through a business directory of careers before helping shape the Sarasota streetscape as an important developer in the 1920s. He began his career in Chicago in a haberdashery and ran a grocery and then a restaurant and wound up in the Chicago political machine. He then began manufacturing furniture before shifting into constructing buildings. In Sarasota he erected the the Mira Mar Apartments in 1922, receiving the largest individual building permit ever issued by the city to that point. The Spanish Mission style of this two-story hotel, constructed about the same time, complements the Mira Mar.

TURN RIGHT ON PALM AVENUE. AT THE INTERSECTION OF MAIN STREET, ON YOUR LEFT IS...

15.
American National Bank
1330 Main Street at Palm Avenue

This is the only one of the earliest Sarasota skyscrapers to retain its original appearance. That is a Neoclassical look provided by Ohio-born architect Francis P. Smith who settled in Atlanta and enjoyed a career of over 60 years. Completed in 1926, the nine-story tower follows the convention of designing high-rise buildings in the manner of a classical Greek column with a defined base (the impressive stone street level), a shaft (the unadorned central stories) and a capital (the decorated top floor). The American National Bank had organized in 1925 in the optimism of the Florida land and closed its doors on May 15, 1928 after less than two years in its new home. In 1936 the building was converted into a 125-room Orange Blossom Hotel. Since the 1960s the building has done duty as apartments but through various modernizations has retained its classical exterior visage.

ACROSS THE INTERSECTION, TO YOUR RIGHT IS...

16.
Palm Tower
1343 Main Street at Palm Avenue

This building began life as a two-story boarding house that was transformed into seven stories and became Sarasota’s first skyscraper, although developer W.H. Pipcorn of Milwaukee probably wouldn’t recognize it today. It operated as the Hotel Sarasota until 1974.

CONTINUE ON NORTH PALM AVENUE AS IT BENDS ACROSS COCOANUT AVENUE.  

17.
Sarasota Woman’s Club
1241 North Palm Avenue at Cocoanut Avenue

The Sarasota Woman’s Club has its roots in the Town Improvement Society that began agitating for streetlights and sidewalks in 1903. In 1915 the Woman’s Club moved into this low-slung Tudor Revival clubhouse that also housed the town library until 1941. The club moved on in 1976 and the building became the home of the Florida Studio Theatre.

18.
Frances-Carlton Apartments
1221-1227 North Palm Avenue

Frances was Tampa architect Francis James and Carlton was the name of developers Carlton Olin Teate, Junior and Senior. The complex of Spanish-Moorish style buildings was constructed in 1924 as furnished apartments. James designed the project in tandem with Alex Browning who was responsible for many of Sarasota’s earliest buildings. In the business listings of the 1924 Sarasota Directory, Browning is the only listed architect. The pink stucco was of a darker tint in its fledgling days but the distinctive multi-paned windows - different on each of the three stories - looks the same. When the apartments opened, both Teates moved in.  

19.
F.A. DeCanizares House
1215 North Palm Street

This house was known as Chateau Petite when it was moved here in 1923 but it was anything but exotic - merely a squarish wooden two-story box stripped of any ornamentation. Once here the developer gave the exterior a Mediterranean Revival makeover with stucco and pre-cast ornaments. The roofline was given a stylish shaped parapet and one-story wings were added, including a porte-cochere. The house was purchased by Frederic A. DeCanizares of the Philadelphia suburbs as a winter home.

20.
L.D. Reagin Residence
1213 North Palm Avenue

This Mediterranean-style two-story structure was designed by Thomas Reed Martin and is representative of his work that helped popularize “Floridan Architecture.” Today a restaurant, it was constructed as a house in 1926 for Leslie D. Reagin, owner and editor of the Sarasota Daily and Weekly Times. The paper went out of business in 1929 shortly after the stock market crashed and Reagin went on to serve as Postmaster of the City of Sarasota from 1933 until his working days ended in 1945.

TURN RIGHT ON TAMIAMITRAIL. TURN RIGHT ON 1ST STREET.

21.
Sarasota Times Building
1216 1st Street

The Saratoga Times was reporting the events of the town back in 1899 before there was an official town. When L.D. Reagin purchased the paper he moved the operations from Main Street to this property next to his house. He hired esteemed architect Dwight James Baum, designer of the Saratoga County Courthouse and other prominent buildings, to come up with a new Times building. Well versed in Spanish Mission architecture from his travels in Southern California, Baum created one of his most successful Spanish Eclectic buildings here. On the First Street facade notice the use of three different door types and surrounding frames.  The Sarasota Times unfortunately scarcely lasted long enough to leave ink stains here as it folded in 1929 but the building has survived; currently it has been adapted for a restaurant.

22.
The Gompertz
1247 1st Street

The Levinson family opened the Park-Seventh Movie House in this building in 1925 but went dark during the Depression. Since then there have been long stretches of vacancy and four name changes. Today the salmon-hued Mediterranean-style building is part of the Florida Studio Theatre, featuring a 160-seat performance space. 

23.
Warren Building
1269 1st Street

This delightful Mediterranean Revival commercial building was constructed in 1926; the “Warren” was realtor Clark Warren - “He knows where money grows.” The building was spared a date with the wrecking ball in the 1990s and rehabilitated.  

24.
Selby Public Library
1331 1st Street

The first books were lent in Sarasota in 1907 after Colonel John H. Gillespie donated 300 books from his personal collection and provided a room in the Sarasota Bank for their dispersal. In 1939 the City of Sarasota assumed control of the library with a $5000 yearly budget and built a library on North Tamiami Trail. This facility, designed by Eugene Aubrey, opened in 1998 with space for 300,000 volumes - a thousand times to size of the original collection.

WALK BACK TO PINEAPPLE AVENUE AND TURN LEFT.

25.
Edwards Theater
61 North Pineapple Avenue

Arthur B. Edwards was born in the area before it was even settled and was a life-long promoter of Sarasota during a life that lasted 95 years. When it became a city in 1914 he was mayor and the centerpiece of his vision of Sarasota as a world-class resort city was this theater. Constructed in 1926 and given crisp Mediterranean design by Roy Benjamin, the multi-use building featured shops behind its arcaded street level, offices on the second floor, including Edwards’ own insurance and real estate office, and furnished apartments on the third floor. The 1500-seat auditorium was configured for touring vaudeville acts, opera performances and silent films. Opening night featured concerts and a screening of the silent comedy, Skinner’s Dress Suit, with Reginald Denny in the lead. In 1952 the Florida Theater, as it was called after 1936, hosted the world premiere of Cecil B DeMille’s paean to the Big Top, “The Greatest Show On Earth.” The movie had included scenes shot around Sarasota with Jimmy Stewart and Charlton Heston in the leads. Later that decade a young Elvis Presley performed here. The Florida Theater shuttered in 1973 and was later purchased by the Sarasota Opera Association which spent many years renovating the building prior to a re-opening in 1993. Look up at the corner to see a rendering of “The Opera Imp” sculpted by Ethelia M. Patmagrian.

CONTINUE ON PINEAPPLE AVENUE TO FIVE POINTS AND THE START OF THE WALKING TOUR.