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Biking Central Florida's West Orange Trail

Author: JimmyBoi2
Date of Trip: October 2010



Here is the original Sadler home, built in 1906. It replaced the original 1880's structure, which was divided into two parts and set behind this house. People did sensible things like that back then.

In beautiful downtown Oakland is this home, which -- when the town was a thriving, busy railroad town featuring hotels, an opera house, and more -- served to house workers for the different railway yards.This was built around 1875.

The Oakland Town Hall, right there on the bike trail.

At one time this home featured a sign that said "The 1879 House." It's on the northwest corner of Brock Street and Oakland Avenue (438).

Another dignified Oakland lady.

This home was once the dining annex for the Oakland Hotel, which was attached at the left. The hotel was built in 1910 but this house stood in 1890.

The tumble-down walls above, on Tubb Street, are all that remain of the Smith estate; they now front a new subdivision. Grace Mather Smith lived here with her husband at the turn of the twentieth century, and she was -- compared to the rest of Oakland's more sober Protestant citizens -- somewhat of a hellion: she liked to give parties, dance, and play golf. There's this story: Grace was speeding into Orlando one day for an item she needed for a party, and was stopped by the police and told she'd have to pay a speeding fine of ten dollars. She handed the officer a twenty dollar bill and said "keep the change, I'm coming back through here like hell in a few minutes!"

monolithic first baptist church floridaGrace and her husband built the West Orange Country Club south of Tildenville on Avalon Road. Up until some years ago, its labeled brick archway still stood, but it appears to be gone when I look on Google Earth. It was built to resemble Grace's walls.

A closer look at Grace's wall, fronting a new house. And in the center of town near the Town Hall and post office is a small green called Grace Park, established by the Smiths near a hundred years ago.

The dock at the north end of Tubb Street facing Lake Apopka. I had a nice chat with this guy about alligators.

These are piers which once supported a much larger dock that featured a bandshell.

Just south of the northernmost house on the east side of Tubb Street, this home's front porch once collapsed to the ground due to overcrowding during a wild party. Don't you wish you could have been there? The Manhattans must have been REALLY good.

An orange grove in the center of Oakland.

Centennial Plaza in downtown Winter Garden. The trail goes right through the heart of this cool little town to the east of Tildenville.

Downtown Winter Garden.

Monolithic First Baptist.

Down one of the side streets in Winter Garden. I could live in this little apartment house!

City Hall in Winter Garden -- a deco dream.



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