The Railroad:

Florida’s Boston Herald Locomotive
The year 1879 was Do-or-Die for the City of Orlando. As Mayor Munger had dissolved the city by proclamation in July, concern for the future naturally was on the minds of everyone. The county had been getting closer than ever to getting a much-needed railroad, but with Orlando dissolved, railroad organizers had little choice but to threaten to bypass the county seat.
Orlando had been attempting to out-grow its 417’ x 417’ cow-town reputation since the town’s 1875 incorporation. Failed attempts to secure an operating railroad in 1870, 1874, 1878, and now again in 1879, however, threatened the survival of a sprawling wilderness cow-town. As the county seat approached its 23rd Anniversary as a village, landowners were well-aware that without the county seat title, Orlando could become yet another Central Florida ghost town.

1875 Orange County Courthouse , Orlando, Florida
Property owners north of Orlando knew well the importance of resolving the railroad dilemma. Thousands of citrus trees had been planted on the outskirts of town, particularly in Section 13, where James W. Wilkinson had begun planting his grove in 1873. Surrounding Wilkinson by 1879 were the groves of Dr. Shattuck of Pennsylvania, and John Sinclair of New Hampshire. James Peery Sanxay, of Brooklyn, New York, and others.
One could argue that the railroad was in some ways more important to Section 13 landowners and their neighbors than the county seat itself.
The Problem:
Orlando’s William Allen Patrick and Palatka’s Robert R. Reid were both claiming to be rightful owners of an L shaped 120 acres surrounding Orlando’s Courthouse. Visitors in 1879 had to walk across the disputed land to enter the Courthouse building.
Four years earlier, over the summer of 1875, local landowners agreed that Orlando needed to be incorporated. They even agreed to enlarge the town’s size from its 417’ x 417’ four acres to 640 acres - one-square mile of undeveloped land having the courthouse steps as ground zero. But absent from the 1875 meeting were Patrick and Reid.
“Questions were raised about the legality of the city’s incorporation,” wrote Historian William F. Blackman in his 1929 History of Orange County, “causing the citizens to decide that they should dissolve their city,” so Mayor Munger did just that in July of 1879.
Dissolving Orlando, however, raised serious concerns for railroad planners hoping to start laying iron rails southbound from Sanford within the coming months. Historian Sherman Adams, in 1884, wrote that the railroad announced that it would not enter the county seat unless it could be assured that it would receive a clear title from the property owners.
The threat to bypass Orlando meant a train would run either one mile east of the courthouse or one mile west of the courthouse. Either way, that spelled disaster for the county seat and growers on the northern outskirts of town – like those in Section 13.

Altamonte: A History of Altamonte Springs, Florida
Seminole County Historical Society’s Quarterly Meeting
Tuesday, January 14, 2025 at 7PM
Casselberry Recreation Center at Triplet Lake
The Resolution:
Desperate times, as they say, call for desperate measures, an age-old saying that is appropriate in explaining how Orlando approached its 1879 moment of truth. To rescue their county seat the citizens looked first to its oldest county citizen, the one resident most knowledgeable of how the Orange County seat had come into existence a quarter century earlier.
James G. Speer, 58 years of age in 1879 and a resident of West Orange County, the lawyer who in 1856 participated – along with his first wife – in founding a village of Orlando, was recruited to make a long arduous journey to Talladega, Alabama. The trip, if successful, was to be step one in a series of legal maneuvers necessary to resolve Orlando’s land ownership problem.
On 5 October 1857, Attorney Speer had conveyed a deed gifting four acres to Orange County for a courthouse from “Benjamin F. Caldwell of Talladega, Alabama.” As Caldwell had been a casualty of the Civil War, Speer instead went to Talladega to get a signed release “from the heirs of Benjamin F. Caldwell.” James G. Speer witnessed the signatures on 21 April 1879 of “Louise, the widow of Benjamin F. Caldwell of Cass County, Texas, and William S. Caldwell, Benjamin F. Caldwell Jr., sons of said Benjamin F. Caldwell Sr., deceased, all of Talladega, Alabama,”
Benjamin F. Caldwell, the donor of land for the courthouse at Orlando, had been the half-brother of James G. Speer’s first wife, Isaphoenia Cleopatra (Ellington 1820-1867) Speer.
The living heirs of Benjamin F. Caldwell transferred any rights they might have had on the land surrounding the Orange County courthouse to Robert R. Reid of Palatka, Florida.
While James G. Speer was returning home from Alabama, Robert R. Reid’s attorney, on 17 May 1879, met with Orange County Commissioners James M. Owens, Benjamin F. Whitner, Henry Overstreet, and Christopher C. Beasley, and stipulated in writing that Robert R. Reid claimed no legal rights to the four (4) Orange County acres, “the same four acres conveyed to the county from by Benjamin F. Caldwell by James G. Speer” on 5 October 1857.
Among the four commissioners accepting the agreement, one especially, Benjamin F. Whitner, was no doubt pleased to learn progress had been made on resolving a dispute that was delaying his long-envisioned railroad corridor.
Attorney James G. Speer filed the Caldwell release on 27 July 1879 with the clerk of court in the dissolved town of Orlando. And with Caldwell now out of the picture, Robert R. Reid of Palatka could begin his next and most important step in finalizing the land conflict.

The Patrick family had been residents of Orlando a dozen years before Benjamin Caldwell gifted four acres for an Orange County Courthouse on land William A. Patrick claimed was his family’s property. The Patrick conflict had been compounded by a deed to William A. Patrick, a deed from James & Mary Yates that had been dated 24 April 1878.
The Yates-Patrick deed of April 1878 is the most perplexing of recorded land deeds because of its recent date. In 1860, James Yates had described his land as limited to 40 acres north of Lot 1 in the 1857 Town Plat of Orlando, whereas the 1878 deed conveyed 120 acres to Patrick. Other deeds complicated the matter even more, but timing called for a resolution to all the confusion.
Backers of the South Florida Railroad had reached an agreement to secure the franchise to build a train to Orlando in February of 1880. They began laying rails that same month, agreeing to have the railroad complete to Maitland, Florida within six months.
Whatever their differences, Robert R. Reid and William A. Patrick had to resolve their dispute, for failure to do so would cost both individuals financially if the railroad failed to enter the town of Orlando.
On 24 June 1880, as the laying of iron rails from Sanford on Lake Monroe approached Maitland, William A. Patrick agreed to settle on 40 of the 120 acres, leaving Robert R. Reid to take 80 of the 120 acres.
Months later, iron rails reached Section 13 north of Orlando, where a new town of Willcox welcomed the arrival of the South Florida Railroad. A Willcox Post Office had been established on 24 August 1880 to make the town on the outskirts of Orlando all the more official.
In Orlando, Robert R. Reid’s 80 acres ran North Street (now Robinson), south to South Street, as did Gertrude Avenue, (now Gertrude’s Walk), the west border of Reid's 80 acres. William A. Patrick’s 40 acres ran west from Gertrude Avenue.
The first South Florida Railroad train arrived in Orlando on 11 November 1880, traveling on track that had been laid north to south down the center of Gertrude Street, the dividing line between Patrick’s land on the west and Reid’s land on the east.
Orlando had been saved not by the ringing of a bell, but rather by the blowing of a South Florida Train’s whistle. The little remote cow-town wilderness village of 1880 Orlando lived to see not only another day, but another 145 years - and counting!
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