Then the Train Showed Up
If agriculture gave Winter Garden a reason to exist, the railroad gave it somewhere to exist.
Rail service reached the area in the 1880s, and by the end of the nineteenth century multiple rail connections were serving the growing community.
That’s a huge reason downtown Winter Garden is where it is today.
Farmers needed access to transportation.
Packinghouses needed access to trains.
Businesses wanted to be near the people working around both.
So the town grew around the tracks.
Plant Street became the commercial spine, with stores, businesses, packinghouses and residences developing around the railroad corridor.
One person who seems to turn up practically everywhere in early Winter Garden history is Arthur Bullard Newton.
Newton became so involved in the emerging community that he earned the nickname “Mr. First.”
He operated a general store.
He established the local post office in 1892.
He published the town’s first newspaper, The Ricochet.
He worked as a depot agent.
And eventually he became Winter Garden’s first mayor.
That’s a pretty impressive résumé for one guy in a town that was still figuring out what it wanted to be.
According to the City of Winter Garden, Winter Garden was established in 1903 and incorporated as a city in 1908.
By 1920, its population had climbed beyond 1,000, and Winter Garden had become an important agricultural and commercial center for western Orange County.
Oranges and other crops moved from local farms to packinghouses, from packinghouses onto railroad cars, and from Winter Garden to markets far beyond Florida.
The railroad tracks that once defined downtown aren’t carrying those trains anymore.
But the transportation corridor didn’t disappear.
Much of the former railroad route became part of the West Orange Trail.
So when you’re biking or walking through downtown today, you’re traveling along the same basic corridor that helped create the city more than a century ago.
The bicycles are just considerably quieter than the trains.
