Pensacola stakes its claim to 450 years and the oldest European settlement in the United States to a 1559 Spanish expedition helmed by Tristan de Luna sailed into Florida’s largest land-locked deep-water harbor. Luna brought a fleet of 11 vessels with the purpose of settling the area - in the contingent of 1,500 were many builders and craftsmen, including African and Indian slaves. But only weeks after coming ashore a violent hurricane sunk all but three of the Spanish ships and within two years even the most determined of settlers had abandoned the beleaguered outpost. For the next 140 years the only history made here would be the unrecorded activities of the indigenous peoples who lived here.

Late in the 17th century the French began actively poking around the lower Mississippi River and the Spanish constructed a fort in 1698 to guard the perimeter of their North Americans possessions here. One would be the Spanish construct of Fort San Carlos de Austria that would lay the foundation for what would become Pensacola. Their fears were not unfounded - the presidio would be sacked by the French in 1719. That began a stretch of 100 years where Pensacola would be controlled by the French, then the Spanish, then the English, then the Spanish again and finally, in 1821, the Americans. Andrew Jackson took possession of the Florida Territory for the United States in Pensacola and was made Territorial Governor. Jackson, never comfortable with the Spanish culture, stayed about four months and was back in Tennessee when the first legislative council of the new Territory of Florida convened here in 1822.

Pensacola was early Florida’s largest city, although it didn’t grow much beyond its treasured port. At the outbreak of the War between the States in 1861, when Confederate troops seized the town it was four blocks wide and about eight deep. In the last decades of the 19th century, after fire gutted the business district in 1880, Pensacola boomed with great stores of timber and lumber shipping out of port and America’s greatest catch of red snapper steaming in from the snapper banks of the Yucatan Peninsula.

Pensacola’s fabric has been interwoven with the United States military from its earliest days when President John Quincy Adams established a Navy shipbuilding yard on the southern tip of Escabambia County to take advantage of the hard and curvy wood of the abundant live oaks that grow there. In 1914 the United States Navy located its first naval aviation training base in Pensacola, bringing tens of thousands of recruits to town. A century later “The Cradle of naval Aviation” is still the town’s defining identity.

Another nickname for Pensacola is “The City of Five Flags” for Spain, France, Great Britain, the United States and the Confederate States of America. Of these, our walking tour will encounter the influence of this jumbled heritage. There will be the orderliness of the British street grid and the high balconies and wrought iron railings reminiscent of French settlements west of Florida and cottages constructed in the Spanish Colonial era and we’ll start, appropriately, at the spot where Pensacola once changed ruling hands...

1.
Plaza Ferdinand VII
bounded Palafox, Jefferson, Government and Zaragoza streets

This has been an open space since the first Spanish occupation and was used by the British as a drilling field. It picked up the name Plaza Ferdinand VII for the King of Spain beginning in 1813. When Florida became an American territory General Andrew Jackson was sworn in as first Territorial Governor in this plaza, now a National Historical Landmark. The large obelisk in the square remembers Colonel William D. Chipley, railroad tycoon and one-time mayor of Pensacola.

EXIT THE PLAZA AT THE SOUTHEAST CORNER, ACROSS JEFFERSON STREET. 

2.
T.T. Wentworth Jr. Florida State Museum
330 South Jefferson Street

This handsome Spanish Mission style building was constructed in 1907 as the Pensacola City Hall and housed the city government until 1985. The symmetrical yellow brick building features a central parapet over an arched entrance. A quartet of square towers are topped by wide bracketed eaves and a red tile roof. The building was adapted to house the collection of T.T. Wentworth, a cornucopia of eccentricities that began as a roadside stand. Wentworth’s treasures grace the first floor and the rest of the building is devoted to Florida Panhandle history and a science museum.

TURN RIGHT ON JEFFERSON STREET, WALKING TOWARDS THE BAY.

3.
Pensacola Cultural Center
400 South Jefferson Street

Mobile architect Rudoph Benze designed this monumental Neoclassical structure for Escambia County as the Court of Record in 1911. It is actually two matching buildings linked by a courtyard. Among its functions was as a court and jail space. On the third floor was a built-in gallows where hangings took place until 1920. The jail cells were ripped out in a post World War II renovation. The building was closed when the county departed in 1978 and renovated by the Pensacola Little Theatre (PLT) with a centerpiece three-story performance space. The PLT was organized in 1936 by the Works Progress Administration, which created theater companies across the country as part of the federal government’s recovery program after the Great Depression.

4.
Pensacola Museum of Art
407 South Jefferson Street

This two-story Mission Revival structure was built in 1908 as the city jail. The first perps were hauled to the jail in a horse-drawn paddy wagon called “Black Mariah.” The building served as a prison until the 1950s when a modern facility was constructed. The Pensacola Art Association moved in and transformed the old cells into gallery space. In 1982, the building became known as the Pensacola Museum of Art, and in 1988 the museum, with permanent collections that include works by Alexander Calder, Andy Warhol, Pablo Picasso, Salvador Dali, Thomas Hart Benton and Louis Comfort Tiffany,  finally purchased the building from the city.

TURN LEFT ON MAIN STREET. CROSS THE RAILROAD TRACKS AND CONTINUE PAST BARRACKS STREET.

5.
Louisville & Nashville Terminal
207 East Main Street

Chartered in Kentucky in 1850 the Louisville & Nashville Railway, familiarly known as the L & N, survived the Civil War and was a dominant line for 132 years. This terminal was constructed in 1892, providing a link between the ships in port and the freight cars on the train tracks for the lumber and fish that flowed across the docks. The building has been restored to its Victorian Stick Style appearance with prominent bracketing and eclectic roofline. 

TURN LEFT AND WALK INTO FOUNTAIN PARK AND UP TO ZARAGOSSA STREET. ACROSS THE STREET IS...

6.
Seville Square
Adams and Alcaniz streets between Zaragoza and Government streets

This and Plaza Ferdinard VII were the only two blocks retained as public squares when the original Spanish settlement was divided into building lots by the British in 1784. Traditionally Seville Square was used as a marketplace. Under British rule soldiers could be found parading here. The 1.7-acre oak-filled park became the centerpiece of the historic residential area; its centerpiece gazebo was added in 1981.

TURN RIGHT ON ZARAGOSSA STREET.

7.
William Fordham House
417 East Zaragossa Street

This single story Folk Victorian Cottage was built as a wedding present in the mid-1870s by Don Francisco Moreno for his daughter Laura on the occasion of her marriage to William Francis Fordham, a doctor who hailed from New Orleans.

8.
Perry House
434 East Zaragossa Street 

This pyramidal cottage was constructed in 1882 with four equal-sized rooms. Floor-length windows provided ventilation and access to the porch area, an arrangement found on many town homes. Charles Perry was a local ship’s navigator who went on to become an officer of A. H. McLeod, a sail-making firm.

TURN RIGHT ON SOUTH FLORIDA BLANCA STREET. 

9.
Barkley House
410 South Florida Blanca Street

Local shipping merchant George Barkley used bricks salvaged from abandoned British forts to put this house together overlooking Pensacola Bay between 1825 and 1830. Today it stands as one of the oldest masonry houses in Florida and one of the city’s best-preserved examples of a 19th-century High House. The house is owned by the State of Florida and managed by West Florida Historic Preservation, Inc. for the University of West Florida.

TURN AND WALK NORTH ON FLORIDA BLANCA STREET. TURN LEFT ON GOVERNMENT STREET. TURN RIGHT ON ALCANIZ STREET.

10.
Quina House
204 South Alcaniz Street

This cottage was built in 1810 which makes it the fourth oldest house in Pensacola and the only one that has remained in its original location for 200 years. Raised on brick piers, the home was constructed of local pine, cypress and oak and boasts an early colonial-style porch. Desiderio Quina, who operated the first known drug store in Pensacola, bought the house in 1821.

WALK BACK TO GOVERNMENT STREET AND TURN RIGHT. TURN LEFT ON ADAMS STREET.

11.
Clara Barkley Dorr House
311 South Adams Street

Eben Walker Dorr was born in Maine in 1823 into a family that had arrived from England 150 years earlier. The Dorr family moved to Pensacola in 1827 and when Florida became a state his father became the first sheriff of Escambia County. Young Door wound up in the timber business and, unable to serve in the Civil War, managed the mammoth Simpson and Company sawmill in Bagdad. When hostilities ended, Dorr was made a partner. He died during a yellow fever outbreak in 1870 and his timber money trickled down to his widow, Clara Barkley, who used it to build this handsome two-story house in 1872.

12.
Christ Church
405 South Adams Street

Construction on this Norman Gothic church began in 1830, anchored by a two-tiered square tower decorated with battlements and surrounded by a cross. Constructed of locally hand-made brick, the price tag was $4,500. The first services were held here in 1832, making this the oldest church building in Florida still standing on its original site. The parish moved in 1903 and the last service was held in Old Christ Church on Good Friday. The City of Pensacola took possession of the building in 1936 and did a twenty year stint as a public library. Today it is open as part of Historic Pensacola Village.

TURN RIGHT ON ZARAGOSSA STREET.

13. 
Lear-Rocheblave House
214 East Zaragossa Street

John and Kate Lear built this Queen Anne-flavored wooden house in 1890 but split up before ever moving in. Benito Rocheblave, captain of the local tugboat Monarch who ran guns and ammunition to Cuba during the Spanish-American War, settled his family here from 1897 to 1910 but for most of its life the structure has done duty as a boarding house. The two-story veranda features intricate sawnwork details. 

TURN RIGHT ON TARRAGONA STREET.

14.
Museum of Industry
Tarragona Street at Church Street

This low-slung rick building, painted white, was built in 1884 for the Pensacola Ice Company. After almost 100 years of warehouse duty it was acquired by the City in 1968 and is now a part of the Historic Pensacola Village telling the tale of the town’s early industries: fishing/ice, clay/brickmaking, timber and transportation. Parked beside the building is a T.R. Miller Mill Logging Train from 1904.

CONTINUE TO GOVERNMENT STREET AND TURN LEFT. WALK PAST PLAZA FERNIDAND VII TO PALAFOX STREET. THE HIGH-RISE LOOMING OVER THE SQUARE IS...

15.
American National Bank Building
226 South Palafox Street at northeast corner of Government Street

For its new headquarters in 1908 the American National Bank retained architect James Edwin Ruthven Carpenter, Jr., the man most associated with bringing high-rise luxury living to New York City. Carpenter used his $250,000 budget to create one of the most lavishly decorated buildings in Pensacola. Carved ornaments include women’s heads above the over-sized arches. Continuous verticals framing the bays emphasize the height of the ten-story building that was the tallest building in Florida when it was completed and remained the tallest in Pensacola until 1974. The American National Bank did not fare as well as its building has - a real-life run on the bank in 1914 drained its coffers and closed the bank.

ACROSS THE STREET IS...

16.
Escambia County Courthouse
223 South Palafox Street at Government Street 

The federal government established a presence in Pensacola in 1854 with a customs house that cost $60,000 to build. The three-story structure burned to the ground and was replaced with this Renaissance Revival limestone building in 1887. in the 1930s even more room was required so an inter-governmental trade was executed that brought Escambia County here and a new United States Post Office and Courthouse was constructed on the site of the old courthouse. 

TURN RIGHT ON PALAFOX STREET, WALKING AWAY FROM THE BAY.

17.
First National Bank
213 South Palafox Street

Louis Montayne Mowbray and Justin Maximo Uffinger Sr. formed an architectural partnership in 1903 and quickly establish a reputation for creating classically formed bank vaults. This opulent Beaux Arts confection, rendered in pure white marble on a base of dark Maine granite in 1906, was one of their earlier designs. It boasts twinned fluted Doric columns supporting a lavishly decorated pediment and fine ironwork. After a century of service in the financial industry the building became part of the Escambia County Government Center.

18.
Saenger Theatre
118 South Palafox Street

Armed with degrees in pharmacology from Johns Hopkins University, brothers Abe and Julian Saenger moved to Shreveport, Louisiana in 1890. Inside their drug store and soda fountain was a “kinetograph” peep show machine that was operated by the insertion of coins followed by the turning of a handle to display a moving picture. In 1911 the brothers made the leap into the amusement field and built their first Saenger Theatre. They moved to New Orleans in 1917 and built one of the most powerful theater empires in motion pictures with movie houses across the South. Architect Emile Weil was dispatched from New Orleans in 1925 to design the chain’s Pensacola theater. After $500,000, his Spanish Rococo-flavored movie palace and vaudeville hall opened on April 2, 1925 with a screening of Cecil B. deMille’s The Ten Commandments. “The Grande Dame of Palafox” thrived until 1975 when it suffered the fate of most downtown theaters and closed. The Saenger was one of the lucky ones; the University of West Florida brought the venue back to life in 1981.

19.
Thiesen Building
40 South Palafox Street at northeast corner of Romana Street

Christen Thiesen, a Danish seaman, was serving as navigator when his ship pulled into port at Pensacola in 1882. Apparently the ship’s captain figured he could find his own way home because Thiesen was left behind during a yellow fever epidemic. Thiesen pulled through his bout with the disease and found a job tending bar. When the saloon owner died of yellow fever in 1884, Thiesen married the widow and became a saloon owner. In 1901 Thiesen erected this five-story Renaissance Revival building, the tallest in town. It was Pensacola’s first “modern” building with an elevator and steam heat. Some in town ridiculed the project and called it “Thiesen’s Folly.” Thiesen, according to tradition, responded by vowing to fly the Danish flag every April 1, which he did until his death in 1934.  Today’s appearance dates to a 1990s restoration. 

20.
Brent Building
17 South Palafox Street

Pensacola-born and raised Francis Celestino Brent survived the Civil War and returned to town where he accumulated interests in banking and lumber and land. In 1906 he spearheaded the construction of this three-story commercial office building with 240 feet of frontage on Palafox Street. The Brent Building had by far the most square footage for offices and stores in Pensacola. Although the building has lost some of its ornamentation designed by architect Higdon Hawley it retains its century-old form. 

21.
Blount Building
3 West Garden Street at Palafox Street 

William Alexander Blount’s father Alexander gave up his successful law practice that included a stint as North Carolina State Attorney, for a life of plantation farming in Alabama, where young William was born in 1851. After a few years of digging in the dirt Alexander Blount moved the family to Pensacola to resume lawyering and politcking. William and his brother both followed their father’s lead and by 1883 were practicing as Blount & Blount. William Blount also dabbled in real estate, purchasing a three-story building on this site in 1894. After it burned to the ground in the Halloween Night Fire in 1905, Blount set about constructing this building. His son Fernando Moreno Blount served as architect, following the convention of the age of fashioning high-rise buildings in the image of a classical Greek column with a base (the granite-sheathed lower floors), an unadorned shaft (the plain brick center stories) and a capital (the decorative terra-cotta detailing of the upper floors and copper cornice). After it was completed in 1907 the Blount Building spent a few years as Florida’s tallest building.

22.
Masonic Temple
2 South Palafox Street at southeast corner of Garden Street

The building was constructed in 1897 and its first tenant was A.M. Avery Hardware. A.L. Avery had come to Pensacola in the early 1850s and launched a hardware business. His son A. Minor Avery moved the concern, that operated into the 21st century as Pensacola Hardware, here. Its most recent incarnation has been as the Vinyl Music Hall.

WALK ACROSS THE INTERSECTION ONTO THE MEDIAN IN THE CENTER OF NORTH PALAFOX STREET.

23.
Pelicans in Paradise

The Pensacola News Journal brought these colorful five-foot penguins to the Pensacola streets as a public art project. Originally a total of 41 pelicans were painted and planted on cement perches around town. Some were removed and returned to their sponsors but many, like these, remain in their original locations. Here in the intersection of Garden and Palafox streets are Pelicans of all the branches of the armed forces that call Pensacola home.  

CONTINUE UP NORTH PALAFOX STREET ON THE EAST SIDE OF THE MEDIAN (YOUR RIGHT).

24.
Isis Theater
2-4 North Palafox Street at northeast corner of Garden Street

With business going gangbusters at the Saenger Theater down the street in 1938 the Saenger Amusement Company purchased this 1913 building and remodeled it for a second-run theater. Sometimes that run would be on the same night as porters would carry each reel from the sold-out Saenger to the projection room at the Isis. The building ceased to house a theater in 1950. 

25.
Rex Theatre
18 North Palafox Street

This building began life as the Rhodes Futch Collins Furniture Company store. In the 1930s the Saenger Amusement Company purchased the building and refurbished it with a stylish Art Deco makeover to serve as a second-run movie theater. The Rex opened in 1937 and had a forty-year run. In the years since there have been repeated efforts to revive the Rex as an entertainment venue but nothing has survived.

26.
Winston E. Arnow Federal Building
100 North Palafox Street at Chase Street

Works Progress Administration funds during the Depression created this United States Post Office and Court House in 1938. The Spanish Colonial Revival design was provided by architect Rudolph Stanley-Brown, a grandson of President James A. Garfield. The building was vacated in 1998 and after a decade of renovations was re-occupied and named in honor of federal judge Winston E. Arnow, who made a number of landmark civil rights decisions in the District Court of North Florida.

TURN LEFT, CROSS THE MEDIAN AND TURN LEFT, WALKING BACK DOWN NORTH PALAFOX STREET (TOWARDS THE BAY AGAIN).

27.
St. Michael Church
19 North Palafox Street

With roots extending back to 1781, this is the oldest congregation in Pensacola. The current Gothic-flavored sanctuary, that replaced a wooden church which burned in 1882, was dedicated on June 6, 1886. The church was constructed at a cost of $27,000. The exterior walls, now stuccoed, were of the very best red brick; the interior woodwork was all Florida pine, stained and polished. Pews, with the date stamped on the bottom of each, were added in 1897.

28.
United States Courthouse
1 North Palafox Street

For most of the 20th century this prime location was the site of the posh Hotel San Carlos. The grand hotel was demolished in 1993 and replace with a new United States Courthouse in 1998.

TURN RIGHT ON GARDEN STREET. TURN LEFT ON BAYLEN STREET AND WALK THREE BLOCKS TO GOVERNMENT STREET. TURN RIGHT.

29.
St. Joseph Catholic Church
140 West Government Street

The Sisters of Mercy opened St. Joseph Colored and Creole Schools in 1877 and the St. Joseph Catholic Church, a two-story frame structure, was dedicated on December 4, 1892. It was the first black parish in the Diocese of Mobile. Plans were hatched almost immediately for a sturdier brick building and this Gothic Revival church was dedicated and holding services less than 18 months later.

TURN LEFT ON SPRING STREET. 

30.
Pensacola City Hall
222 West Main Street at Spring Street

This is the latest building to house the offices of the City of Pensacola, coming online in 1987. After Hurricane Ivan, the 10th most intense Atlantic hurricane ever recorded, struck in 2004 an inspection for damage revealed substandard work and caused the building to be closed for two years.

31.
Site of the Panton-Leslie Trading House
northeast corner of Spring Street and Main Street

Alexander McGillivray was a Creek chief and son of a prominent Scottish trader who was facile in both Spanish and British society. He negotiated treaties and alliances and built a trading monopoly with the Indians in the 18th century by playing the British, Spanish and Americans off of one another. As a result, he amassed a tremendous fortune in slaves, cattle, and land and became one of the most powerful Creek Indians of his era. Under Spanish rule after 1783 McGillvray found a reliable supply of quality European goods hard to come by and he entered into a deal with a new mercantile firm of Scottish traders founded by 38-year old former British governor of East Florida, William Panton. Panton, Leslie & Company established its headquarters here to oversee an empire that extended to the Mississippi River. There is no trace of the Panton-Leslie store but the property is marked by a model of the store. When Colonial rule ended the Indians lost their leverage as trading partners and Patton-Leslie gobbled up three million acres of Indian land to pay off bad credit debts.

TURN LEFT ON MAIN STREET. 

32.
Bear Block
402 - 410 South Palafox Street

Bavarian immigrant Lewis Bear arrived in Pensacola in 1876 and set up shop as a grocer and ship chandler. The enterprise prospered and by 1892 Bear was able to move into this classically appointed warehouse and store. Bear would die in 1895 but the company reorganized with his sons Morris and Max at the head of the business. In 1901 the Bears signed an agreement to distribute Budweiser lager beer an arrangement that has kept the Lewis Bear Company humming for more than a century. Although the company left downtown in the 1950s, the Bear Block, with its ornamental cast iron arcade, retains its 19th century appearance. 

TURN LEFT ON PALAFOX STREET TO RETURN TO THE TOUR STARTING POINT IN PLAZA FERDINAND VII.