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The streetcar system in Pensacola can be traced to [[Conrad Kupfrian]], a German immigrant who was reportedly inspired by the horsecars he saw in St. Louis on a business trip. He formed a partnership, the [[Pensacola Streetcar Company]], with [[John Henry Pfeiffer]] and [[John Cosgrove]]. The men raised $50,000 in capital for the project and, on [[November 15]], [[1882]], convinced the [[Pensacola City Council]] to pass an ordinance allowing steel track to be placed in the roadways. The first streetcars, which went operational in [[1884]], ran from [[Pensacola Bay]] north along [[Palafox Street]] to [[Wright Street]], then east to the [[Union Depot]], then south along [[Alcaniz Street|Alcaniz]] to [[Gregory Street|Gregory]] and west to [[DeVilliers Street]]. A north-south link at DeVilliers went south to [[Government Street]] and east again to Palafox. A general fare cost five cents, and cars passed about every ten minutes during high-traffic periods. The company addressed the issue of low ridership after business hours by creating an amusement park destination, called [[Kupfrian's Park]], in the [[North Hill]] neighborhood, extending the line west from DeVilliers on [[La Rua Street|La Rua]] and north on [[J Street]].

==Demise of the streetcar system==In 1928 the [[St. Louis-San Francisco Railway]] bought the old dummy line for freight purposes; a bit of trackage still exists on the south side of Main Street between Clubbs and A, where the line curved southwest toward Pine. In [[1929]], the City passed an ordinance authorizing Gulf Power to discontinue service and remove trackage for the portion of the system servicing the [[Hawkshaw]] area.<ref>Ordinance No. 7, Series No. 19, City of Pensacola. [[August 5]], [[1929]].</ref> The City authorized Gulf Power to surrender its streetcar franchise in November [[1931]], "in consideration" of an $18,000 credit to be applied towards the City's debt to Gulf Power.<ref>Ordinance No. 10, Series No. 1, City of Pensacola. [[November 30]], [[1931]].</ref> After adoption of the ordinance terminating the franchise, Gulf Power agreed to reduce the interest rate on the City's debt from eight to six percent per year.<ref>Contract between Gulf Power and the City of Pensacola dated December 31, 1931.</ref> Streetcar service was discontinued in [[1932]], replaced by motor bus service operated by the [[Pensacola Coach Corporation]]. At its peak, a total of 30 trolley cars carried four million passengers per year (1920).<ref>[http://www.dot.state.fl.us/publicinformationoffice/historicdotphotos/rail/pentrolley.htm MyFlorida.com]</ref> Partially covered tracks and barely concealed right-of way are clearly visible in various places along the former routes, including on West [[Gadsden Street]], West [[DeSoto Street]],<ref>[http://maps.google.com/?ie=UTF8&ll=30.422958,-87.220094&spn=0.01286,0.019312&z=16&layer=c&cbll=30.422841,-87.219968&panoid=DKB9xa_j9I6kFEHTAn8nmg&cbp=12,259.17608183457696,,0,14.54100241579118 Google Maps Street View]</ref> and East [[Jackson Street]].<ref>[http://maps.google.com/?ie=UTF8&ll=30.418702,-87.209151&spn=0.01286,0.019312&z=16&layer=c&cbll=30.422921,-87.196446&panoid=ynzkZ_-A2Lj1l73a8mwYUw&cbp=12,76.9141215041957,,0,3.1568518060403385 Google Maps Street View]</ref> The trolley was discontinued six years after Pensacola Electric Company's [[1932]] merger with [[Gulf Power]].

[[Segregation]] of the streetcar system came in [[1905]] via a state law authored by Pensacola representative [[John Campbell Avery]]. Soon after the law was approved by the Florida Legislature, Pensacola's African-American community initiated a boycott of the streetcar system. The streetcar system's management reported on the boycott to the Stone & Webster corporate office:{{cquote|In Pensacola 90% of the negroes have stopped riding even though the company has not issued an order or intimated anything as to what they intend to do. The negroes have appointed Committees who meet negroes visiting their city at the train and present each one with a button to be worn in the lapel of the coat. This button bears the single word WALK.|20px|20px|Letter of John E. Hartridge to William H. Tucker, May 28, 1905.<ref>Ortiz, Paul. ''Emancipation Betrayed''. University of California Press, 2005.</ref>}} However, it the Avery law was declared unconstitutional by the Florida Supreme Court a month later. The [[Pensacola City Council]] responded with an ordinance that was<blockquote>somewhat similar to the state law which was declared unconstitutional. It was drawn however, in such shape that it will hardly be declared unconstitutional if any attempt is made to carry it to the Supreme Court. The street railway company will divide the cars as it did during the time that the state law was being complied with, except that cards will be posted designaling the white and colored parts of a car. The colored population seems to be satisfied and it is not expected that the cars will be boycotted as was the case when the state law bc- [became] operative.<ref>"Jim Crow Law Effective To-Day." ''Pensacola Journal'', October 13, 1905.</ref></blockquote>