Home' The River Weekly News : RWN 121115 Contents Historic Downtown Fort Myers, Then And Now:
Winding Through McGregor’s History
by Gerri Reaves, PhD
Fort Myers is known around the world for historic McGregor
Boulevard, a classic thoroughfare lined with royal palms.
Soon, the city’s Flexible Pavement Reconstruction proj-
ect will refurbish a two-mile stretch of the road in conjunction
with the Florida Department of Transportation. The project will
involve changes to infrastructure and aesthetics between Poinci-
ana Avenue and Colonial Boulevard.
So, it’s a good time to refresh our knowledge of the iconic
boulevard’s rich history. The very royal palms that inspired the
title City of Palms, as well as the road’s name and two memorials
along its path, reveal important chapters in local history.
What evolved into McGregor Boulevard was first a Seminole Indian trail and later a
military trail during the Second Seminole War (1835 to 1842). When Union soldiers
occupied the U.S. Army Fort Myers in December 1863, they reopened what they
called the Colonel Persifor Frazer Smith Trail to Punta Rassa.
The boulevard also had a history as a cattle trail as far back as the Civil War, and
therefore played a major role in the area’s economic development.
Cowboys drove cattle down oyster-shelled McGregor Boulevard to Punta Rassa for
their shipment to Cuba, the West Indies and Central America. That trade lessened
after the railroad came to town in 1904, but the last cattle drive down McGregor did
not occur until 1922.
In the town’s earliest years, the road was appropriately named Riverside Drive, at
least the section to Manuel’s Branch, which at that time was the far reaches of the
town. In those days, West First Street didn’t exist, and the drive truly lay closely along
The road’s name change in 1915 is multi-part story that involves some of the city’s
most notable benefactors. The modern boulevard is actually a memorial – in fact, a
double memorial of sorts.
Ambrose and Tootie
McGregor came to Fort
Myers in 1891 for the
health of their son, Brad-
ford. The wealthy couple’s
positive influence on the
development of the young
town is difficult to measure.
Ambrose died in 1900,
followed by Bradford’s
death in 1902. Tootie
remarried in 1905, to Dr.
Marshall Orlando “MO”
In 1912, Tootie
McGregor Terry made a
proposal to the City. She
would build a 50-foot-wide
macadam road from Whis-
key Creek to Punta Rassa,
if the city would extend it
from the creek to Monroe
Street in downtown Fort
No longer would River-
side Drive be “paved” with
oyster shells; it would be
a modern road. She also
offered $500 per year for
Both the city council
and the county commission
continued on page 4
THE RIVER - DECEMBER 11, 2015
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and Ken Rasi
Gerri Reaves, Ph D
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Marion Hauser, MS, RD
Ross Hauser, MD
Capt. Matt Mitchell
Cynthia A. Williams
By 1961, McGregor’s majestic royal palms were its signature
look, as seen in this southwesterly view near the Edison Winter
courtesy Florida State Archives
This 1918 northeasterly view of Poinciana Park shows the beginnings of the subdivision boom along McGregor Boulevard, which peaked in 1925. The Caloosahatchee River is visible in the
distance to the left of the Myron and Carrie Patch house.
courtesy Southwest Florida Historical Society
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