Where the Roads Take You: History of Winter Garden's streets Part 1

Plant. Tilden. Boyd. Dillard.

Every day, folks travel the roads and streets of Winter Garden, yet many residents don’t know the history behind the names. Some were named for the area’s first settlers, and others likely were named for the earliest families who lived along the route.

The Winter Garden Heritage Foundation has an extensive collection of family files that chronicle the earliest pioneers’ journey to the area and the lives of the residents who lived here before us.

At turn of the 20th century, only a handful of families lived in the area — J.L. Dillard, J.W.F. Bray, W.P. Vining, E.D.M. Perkins and G.W. Swan were the heads of these pioneer family households.

As more people came to the area, roads were carved out and named and maps were created to record the city’s boundaries and provide a formal guide.

In an article on maps in the Winter 2016 issue of the WGHF newsletter, Jim Crescitelli writes: “In our collection are the Sanborn Water and Fire Maps of Winter Garden and Tildenville, dating from 1917 and 1924. The 1917 edition contains nuggets of information. … Both of the Sanborn maps show all the structures on downtown streets … (and are) layered with updated graphics literally pasted on through the 1950s.”

How did these streets in the historic section of Winter Garden get their names?

PLANT STREET

It is believed that Plant Street was named for Henry Bradley Plant (1819-1899), the founder and president of the Plant System of railways, steamship lines and hotels. He organized and served as president of the Southern Express Company, Texas Express Company, Plant Investment Company and Plant Improvement Company. Plant developed and promoted the west coast and central sections of Florida.

TILDENVILLE SCHOOL ROAD and TILDEN STREET

The Luther Fuller Tilden family and descendants, no doubt, had a great impact on West Orange County, as several streets, an elementary school and a small community are named for the Tildens. Generations of the family were involved in the lucrative citrus business, and many of them lived in the Tildenville.

L.F. Tilden, born in 1834, moved to the area for health reasons when he was in his 40s. He bought 561 acres from William C. Roper for $9 an acre. His first Winter Garden homestead was constructed from the pine trees that grew on land he owned in Apopka; they were rafted across Lake Apopka to his new residence he shared with his wife, Emily Willis, and four children.

This house and another one built by Tilden still stand today at 632 and 634 Tildenville School Road.

Tilden successfully grew tomatoes, citrus and sugar cane, and he and his sons, Charles H. and Luther Willis, earned a reputation for his fruit and vegetable practices. He established churches and schools in the area and donated a large piece of land for Lakeview High School (now Lakeview Middle) in 1927.

DILLARD STREET

James Lafayette (1858-1942) and Mattie Agnes Showalter (1854-1922) Dillard came to Winter Garden in 1887, when deer, panthers and bears roamed the territory, according to an article in a 1934 issue of the West Orange News.

They settled in an area then known as Washington Place, which is now a part of incorporated Winter Garden. J.L. Dillard built the first house on the street that now bears his name — at the southeast intersection of North Dillard Street and Agnes Street. Their second home was at Dillard and Newell streets. The Dillard homestead extended from Ninth Street, north of Plant Street, west to Boyd Street and north to Tilden Street.

They had three children: Marvin, Mabel (Mrs. L.A. Grimes) and Gladys (Mrs. J.C. Bowyer). After the death of his first wife, he married Francis “Frannie” Bedingfield, a widow, and had one daughter, Jimmie Lee Dillard McClung.

Dillard donated the property for the First Baptist Church Winter Garden, planted the first lettuce fields in the area, owned a packinghouse on South Dillard Street, was a well-known truck farmer and became one of the leading fruit and vegetable producers in the area. He served on the first city council (1908) and county commission and in the 1918-19 session of the Florida Legislature.

J.L. developed other businesses and pursued other interests. The Dillard & Boyd General Merchandise store stood at the corner of Plant and Main streets. He acquired large real estate interests, developed housing and, with business partner B.T. Boyd, built many of the commercial brick buildings in downtown after fire destroyed the wooden business district of Winter Garden. 

In recollections of his 1908 arrival in Winter Garden, written in 1940, W.B. Burch said Dillard had the only garage in town, M.V. Dillard & Co., at the northwest corner of Plant and Main streets. In her memories, recorded in 1977, Mabel Dillard Grimes recalled her father wanting to sell cigars, so he brought some from Tampa and set up shop on Plant Street above the garage. The cigar business wasn’t much of a success, she said.

AGNES STREET

The first home of James L. and Mattie Agnes Showalter Dillard was at the crossroads of North Dillard and Agnes streets; this street possibly could have been named for her.

BOYD STREET

Benjamin Thomas Boyd, who served as president of the Bank of Winter Garden for years, was a business partner of James Lafayette Dillard. Dr. H.M. Boyd was a physician and surgeon in office in the Dillard and Boyd Building.

In 1909, the year after the city of Winter Garden was incorporated, B.T. Boyd was elected as an alderman.

(NEXT WEEK: Part 2)

All maps and photos courtesy of the Winter Garden Heritage Foundation: