PhotoBike Tour 16– Oakland and West Orange County, Florida

Looking north along Florida’s Turnpike from the bridge on the West Orange Trail. This highway takes you, eventually, to Wildwood, where it meets Interstate 75. Follow 75 north and you will, after a few days, be on Michigan’s Upper Peninsula which is, for all practical purposes, Canada.

OFFSIDES!! Biking the West Orange Trail is an excursion into the past, a central Florida which hasn’t existed for over a hundred years. I don’t think most people realize the pedigree of the little towns and unincorporated communities they speed through on their bikes, skates, or even their feet. It’s great to schuss from the Lake County line east to Winter Garden, where you’ll stop to have lunch or a drink or browse the cool little shops; the direct line keeps you on the Trail, but i wonder how many people actually go offsides? I like to explore, and prowl. I see a dirt road, or a path leading through the orange groves, or a lonely side street… and there I go. I figure I’m on my bike and can make a speedy getaway if somebody starts yelling at me or chasing me, though so far that hasn’t happened in a big way. I respect private property, and seldom venture to intrude: if my curiosity gets the best of me in a potentially tender situation, I collar the nearest human and ask permission to prowl or take pictures. So far, everyone has said yes; there must be something about my face that disarms people. Or maybe they think “look at that poor idiot on his bike… let’s be nice to him.” This past Sunday I biked a good twenty miles or so in and out of Oakland and the communities of Killarney, Tildenville, and Hull island. Hull Island? Yes, Virginia, it exists for real as much as it does in your imagination… Near where the Trail crosses Deer Isle Road is the site of the Jones General Store at Killarney, an area settled in 1880. Here, a sawmill office, post office and general store were sited at various times in one building. You can still see part of the foundation.

This is the Hull Family monument, which you can see to the left of the bridge just after you cross it going east on the Trail. It says that the Hull Family has been here since 1905, which is a long time for central Florida. (The Pirates of the Caribbean ride isn’t even that old.) You are standing in the vicinity of one of the oldest orange groves in the entire state, though most of the trees are gone and you are lucky if you find some orderly rows of remnants. Hull Avenue in Oakland is named for the family.

Have you ever turned left onto Hull Island Drive while traversing the Trail? Here’s what you’ll find:

It’s a region of old groves and farms that have been worked for  generations, a real slice of Old Florida. And there’s an ashram here too– a slice of NEW Florida.

J.W. Jones Road is accessed just past the foundation of the Jones store, and you can easily bike it to the houses and three mobile home communities (Killarney Court, South Shore, and Gourdneck Village) nestled along the south shore of Lake Apopka. There’s a nice view of the lake, and a residence flying the actual flag of the Confederacy, not the battle flag we are all familiar with.

Continuing east, I paused at the rest stop just west of Oakland, and saw how the trees reaching toward the canopy reminded me of the soaring arches in a Gothic cathedral, which is where they got the idea: from observing how the trees kept themselves standing. Get off the Trail at Pollard Avenue and make a right; it’ll take you directly into the heart of the town’s African-American neighborhood. Here’s where a Masonic Temple stood up until just a few months ago on Sadler Avenue…

Here’s the non-updated image of the Masonic Temple from Google Earth:

I stopped a woman driving by and she explained that there were only a couple of old guys who still went to the Lodge, and that one had recently died, and so that was that.

There are three cemeteries in Oakland– one for white families and two for black families; it’s just the way it has always been.  (The older of the two black cemeteries is hidden in the dense growth west of town, only recently having been “discovered.”) In the white cemetery is the marker for James Gamble Speer, one of the area’s pioneer settlers. He and his family used to all be interred in the family plot on the north shore of Lake John, south of Tubb Street. When the property was sold to a developer, he removed all the headstones, piled them in a corner, and built houses atop the plots. James Gamble Speer (1821-1893) would NOT approve, and I hope he gives them all hell once in a while.

Here’s approximately where the Speer cemetery was located, south of Tubb Street; you go across the bridge that crosses over the Turnpike, and you’re at Lake Johns Circle. I walked through a belt of trees between two houses, and there was the lake. Southwest from here and across the lake is a peninsula which still does have a cemetery on it, nestled in the remaining orange grove.

The black cemetery serves as the final resting place for Samuel Pollard, for whom the street is named. And look… somebody brought him some sandwiches! I noticed a dirt track leading around the northern border of the cemetery, and so I decided to follow it, carefully. I mean, you never know what you will encounter among the trees. All sorts of possibilities entered my feverish brain, most of them ending dimly, but I was spared; I did see some piles of tires, assorted mounds of refuse, but nothing worse. I suppose people use it as a dump driving up off of Highway 50, from which you can see this cemetery. Sad. This path eventually popped me out onto Sadler Avenue, right where the Masonic Temple used to stand. I biked further east to the Vick house on Tubb Street, which used to be an Oakland schoolhouse for a time. It’s apparently the oldest home in Oakland, built as an inn in the 1860s. It became the Vick home in 1903. Beautiful and simple. A bit further east you come to Brock Street… here’s a gem of a house, perfect in its lines and aspect. It bears a resemblance to a home on Tildenville School Road South on Tildenville School Road, just north of where it crosses Oakland Avenue (438) sits this grand old house built in 1908. It was situated cater-corner of its present site until the 1990s when it was sold; the family let it go for a song and the new buyer had to move it to a new lot– thankfully minutes away, since it IS an Oakland grande dame and should therefore have been allowed to stay in the neighborhood. The present owners were on the front porch and graciously answered questions I had about the area, and then they magically invited me inside. (Do I channel Little Jimmy? Does he make an appearance and charm everyone?) I’d been in the house when it was being sold years ago– there was an estate sale then– and I remember it seeming very enclosed regarding rooms and hallways. The house is now so different– structural walls have been opened up, and everything is painted a bright white. Brick Road ends here at Tildenville School Road, a pleasant country lane that goes east to Winter Garden. (Actually, the Winter Garden city limits encompass Tildenville now). Brick Road is a remnany of Highway 22, which crossed the center of the state; Washington Street in Orlando was part of it, as was Story Road in Winter Garden– once also known as Washington Street until it was renamed for the Story family.

This home is located on Brick Road; it was built by a Willis and occupied at one time by Annie Connell, who taught at the old Oakland-Winter Garden School across the way.

Now we travel to south Tildenville, an African-American community separated from north Tildenville by Highway 50 and the Turnpike. The road becomes Avalon Road here. Just past the Turnpike overpass, on the left going south, you’ll find the entrance to the “West Orange, Country Club.” It was built in 1911 by the Mather-Smiths, a prominent Oakland family who found the existing golfing facilities in town too small– the Mather-Smiths loved to party, so they built their own country club and had a ball. All that remains is this archway. (UPDATE: See comments section regarding the existence of the Club’s guest house.)

I love the name: the O Deli.

Back in Oakland, I biked to the Presbyterian church (its third incarnation), hoping to get inside to see the preserved stained glass windows from the second church, which was a beautiful, ivy-covered brick building. It was Sunday afternoon, and services were over, and I wondered how I’d manage. Hmm. An older guy appeared after a few minutes to take down an Easter banner, and I asked about access. Well, everything was closed, services over , the building hermetically sealed, the works… and so I mentioned the stained glass and the guy said “oh yes, right through that church office door, and that’s open.” Oh. So inside I went, and there was this window… and there’s our man James Gamble Speer…

In that lobby area where this window is located, a man and his two young sons were sitting and waiting for someone; he saw me observing the window and mentioned that there was another one down a hall and in another office area. In that direction I could hear a string ensemble practicing, so I followed the sound of the sliding bow and came across a group of people playing in a room off the hall. They all stopped  and looked up as I looked in– the door was open, and their resin  ground to a halt. I was tempted to ask to join them on the flute, or perhaps the tuba, but before I could the conductor, an elegant older woman, asked if I needed help. I mentioned the second stained glass window and one of the ensemblists jumped up and offered to show me where it was. We had to go through the darkened sanctuary, where I almost stumbled into the older guy I’d encountered earlier: “I managed to find my way in here anyway,” I said, and he looked at me like I was crazy, but he did take me to the second window as the ensemblist returned to his practice… and here you see noted our friends the Tildens!

And finally, the Sadler house, built by the family who gives its name to Sadler Avenue. This was also once the house of artist Joe Burch. It receives a memorable Hallowe’en dressing each year. Right here along the road (Oakland Avenue / 438) are the Sadler oaks, planted by the family and now just as much a part of Oakland as the orange groves.

The next time you’re on the West Orange Trail, take a few detours and explore the historical offsides areas– these are sleepy parts of west Orange County that not many people get to see.

Thanks to Steve Rajtar and Eve Bacon for historical footnotes that lead me to these spots…

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21 responses

  1. You really capture how interesting “old Florida” is through these tours. I think the fact that you do so from your bicycle makes our experience as readers much more intimate as a result. Thanks for sharing. (Good for you for cycling in this heat!)

  2. Jim – I live here in Oakland in one of the houses that was part of the Mather – Smith estate. The house was bought by my friends and used as a B&B for several years and is now listed for sale. Oakland is a very unique part of central Florida. It is a very nice taste of what old Florida was really like. I was also witness to the unfortunate fire that burnt the house on HWY50.

  3. Great post! I’ve cycled through this area for years and wondered about many of the things I saw but didn’t know their history — especially the West Orange Country Club Arch to Nowhere. Thank you for the education and entertainment.

  4. Thanks for the pix, they are awesome! I always wondered what the Hull story was. PS that new bridge over Red Bug at the Oviedo end of the Cady way trail was STILL not open last Sunday June 10. I can’t figure out why. Being the good scofflaw that I am, I just go around the barriers.

  5. Nice work. I’ve been a land surveyor in the area since 1969. I was fortunate to see the old groves, and many other sites you mentioned. The history of central florida is very interesting and rich.

  6. Pingback: Deeper Inside West Orange County, Florida: Oakland, Beulah, and “To Kill A Mockingbird” in Winter Garden | What Can I Say ?

  7. I loved reading this article and seeing the pictures really brought back memories for me. As I grew up in Tildenvile some 30 years ago approx. less than a mile from the entrance of the old west orange country club sign/entrance. My grandmother owned a home that unfortuanly burned down several years ago. All that remands is her chain link fence and the overgrown driveway that I as a little girl had walked up & down over some 30 yrs ago. (Land now owned by my mom & sisters) I wonder does anyone have any pictures of the Avalon area or tildenvile area from the early years?! Would love to see them. I bet no one remembers that there used to be a store on the property next to the W.O country club entrance! We used to walk there sometimes if grandma allowed us!:-) you really brought back some special memories! Lastly this past September I built a home directly across the street from my grandma’s land in the new subdivision, Johns lake Pointe which is next to Tucker’s Ranch! I actually saw him a few times..once when he shot at a guy for crossing his bob wire fence~boy did my grandma have some stories about ‘old man Tucker’ as we called him as little girls!
    Thanks for listening… Jamilia

  8. Good stuff on here. The last time I was in the Sadler house the murals Joe Burch did were still on the dining room walls. Joe also did the mural that was behind the desk at the Langford Hotel in Winter Park. If you get to the keys stop in the Sugarloaf lodge and you can see a batik print he did behind the desk, a pirate in the bar and if you stay in the old wing you may just get one of the rooms where he did the landscape murals on the walls. Thanks for the ride.

    • update 9/15 Joe Burch Batik is no longer behind the desk at Sugarloaf Lodge. Still a wing of rooms with original full wall paintings. Remodel got rid of the bar painting too.

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