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Winter Garden’s history of citrus, railways, tractors showcased in two museums

A 1948 caboose sits outside the Winter Garden Heritage Foundation in Winter Garden. (Patrick Connolly/Orlando Sentinel)
A 1948 caboose sits outside the Winter Garden Heritage Foundation in Winter Garden. (Patrick Connolly/Orlando Sentinel)
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Did you know that Elvis once visited Central Florida on tour and learned how to waterski from a local family on Lake Butler? This is only one of the interesting, fun facts that can be gleaned during a visit to one of Winter Garden’s museums, which serve as focal points of the charmingly historic downtown.

The Winter Garden Heritage Foundation oversees the Healthy West Orange Heritage and Cultural Center (home to a visitors’ center and archive), the Heritage Museum and the Central Florida Railroad Museum.

Jim Crescitelli, the foundation’s director since 2012, remembers visiting Winter Garden in the 1970s when citrus groves were abundant.

Jim Crescitelli, director of the Winter Garden Heritage Foundation, stands inside a 1948 caboose that's open for visitors in Winter Garden on May 20, 2024. (Patrick Connolly/Orlando Sentinel)
Jim Crescitelli, director of the Winter Garden Heritage Foundation, stands inside a 1948 caboose that’s open for visitors in Winter Garden on May 20. (Patrick Connolly/Orlando Sentinel)

“I started driving out here because it was so different than Winter Park and Orlando,” he remembers. “There were big old houses, estates and neighborhoods with little wooden houses. It was 1978. It was so quiet around here. I became fascinated by it and started taking pictures, which led to this job.”

Now, Crescitelli oversees the Winter Garden Heritage Foundation’s extensive archive of photos, antique furniture, documents, uniforms, maps and more, plus both museums.

Inside the Heritage Museum, learn about the Native Americans that first inhabited the area and the early days of Winter Garden, which was established in 1903 and incorporated as a city in 1908.

A historic firetruck sits outside the Winter Garden Heritage Foundation and Heritage Museum in Winter Garden on May 20, 2024. (Patrick Connolly/Orlando Sentinel)
A historic firetruck sits outside the Winter Garden Heritage Foundation and Heritage Museum in Winter Garden on May 20. (Patrick Connolly/Orlando Sentinel)

Settlers were attracted to the area in the 1850s, drawn to the soil around Lake Apopka that proved fertile and productive for growing citrus fruits and vegetables. By 1920, Winter Garden had grown to include more than 1,000 residents as its status as a commerce and agricultural center grew. Meanwhile, Lake Apopka became the large-mouth bass capital of the world.

One room in the Heritage Museum is dedicated to the town’s citrus industry with a sign that informs visitors, “Once Winter Garden shipped more vegetables and citrus than any other town in the USA.” A nearby exhibit details the legend of Hoyle Pounds, who opened the Pounds Motor Company in Ocoee in 1913 and then moved his Case tractor dealership to Winter Garden in 1926.

A cast iron eagle from the Case tractor dealership is display at the Winter Garden Heritage Museum on May 20, 2024. (Patrick Connolly/Orlando Sentinel)
A cast iron eagle from the Case tractor dealership is displayed at the Winter Garden Heritage Museum. (Patrick Connolly/Orlando Sentinel)

Pounds’ claim to fame was inventing the rubber tractor tire, replacing the spiked metal wheels used previously. This helped tractors speed up and avoid damaging paved streets.

Before walking a few blocks to the Central Florida Railroad Museum, look inside the 1948 yellow caboose in front of the foundation’s main building.

At the Railroad Museum, see photos of Central Florida’s train depots, maps of historical routes and plenty of signs recycled from a bygone era of rail travel. The current exhibit showcases china plates and other historic pieces from the golden age of the railroad dining car.

Packing labels, logos and artwork from different citrus companies are in display the in Winter Garden Heritage Museum on April 20, 2024. (Patrick Connolly/Orlando Sentinel)
Packing labels, logos and artwork from different citrus companies are on display in the Winter Garden Heritage Museum. (Patrick Connolly/Orlando Sentinel)

While exploring the history of West Orange County, it’s hard to avoid learning about the downturn in the region’s environment and the city of Winter Garden. Growth was hampered by pollution in Lake Apopka and highways that detoured around the city. However, the West Orange Trail and the revitalization of downtown in the last few decades have attracted many new residents and visitors to the area.

After spending time in the air-conditioned museums, it’s easy to spend a day wandering the brick streets and sidewalks between shops and outdoor plazas that invite visitors to sit and stay for a while. Winter Garden maintains its historic charm due to the brick buildings built more than 100 years ago that still stand (including the Pounds building), many of which continue to house businesses and restaurants today.

Find me @PConnPie on Instagram or send me an email: pconnolly@orlandosentinel.com.

China sets from railroad dining cars are currently on display at the Central Florida Railroad Museum in Winter Garden on May 20, 2024. (Patrick Connolly/Orlando Sentinel)
China sets from railroad dining cars are currently on display at the Central Florida Railroad Museum in Winter Garden. (Patrick Connolly/Orlando Sentinel)

If you go

The Healthy West Orange Heritage and Cultural Center is located at 21 E. Plant St. in Winter Garden, right next to the Heritage Museum. The Central Florida Railroad Museum is at 101 S. Boyd St. in Winter Garden. All three facilities are open from 11 a.m.-3 p.m. Tuesday-Saturday. For more information, call 407-656-3244 or visit wghf.org.

Other Winter Garden highlights

  • The SoBo Art Gallery showcases rotating exhibits focused on Floridian creators and emerging artists in a space that was once Winter Garden’s fire station.
  • Garden Theatre is one of the anchors of Plant Street that first opened in 1935 as a single-screen cinema. The historic space is now home to Broadway shows, concerts, movies and more.
  • The West Orange Trail runs for more than 22 miles between Killarney Station, west of Oakland, through Winter Garden and up past Apopka. The paved trail is popular for runners, cyclists and walkers.
  • Winter Garden Farmers Market sees thousands of visitors every Saturday from 8 a.m.-1 p.m. for an outdoor experience with sunflowers, produce, baked goods, crafts, artwork, jewelry, apparel and more.
  • Plant Street Market has 20 vendors with handmade products and natural food, plus Crooked Can Brewing Company.
  • The Historic Edgewater Hotel was established in 1927 and still welcomes overnight guests for a bed-and-breakfast-style experience.
  • Restaurants and shopping abound in downtown Winter Garden, with local options for all kinds of food, drink, gifts and artisan goods.
The history of Florida's railways is on display at the Central Florida Railroad Museum in Winter Garden on May 20, 2024. (Patrick Connolly/Orlando Sentinel)
The history of Florida’s railways is on display at the Central Florida Railroad Museum in Winter Garden. (Patrick Connolly/Orlando Sentinel)

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