Remember the trip around Lake Okeechobee? Well, if you come from the north, there’s some neat historical stuff along the way. You do have to contend with suburban Orlando traffic. ‘Tis the Land of the Mouse, doncha know. But once you get out of St. Cloud, you’ll feel like you’re in the back of beyond. One of the great things about Florida. Even if you’re in a major metropolis, you can find somewhere within an hour’s drive where you’ll feel like you’ve dropped off the face of the earth. I think Florida will always be that way.
We start off in Osceola County, with Disney World’s closest major suburb here (only 13 miles away), Kissimmee. Coming from the north, you can reach it via US 441 or the Turnpike through Orlando, or US 192 from US 27. I’ll give you directions to things scattered around the outskirts, mostly museums. (see Google map)
- Osceola County Pioneer Village and Museum (750 North Bass Road)
- Kissimmee Air Museum / Flying Tigers Warbird Restoration Museum (233 N. Hoagland Boulevard)
- Osceola Center for the Arts (2411 East Irlo Bronson Memorial Highway)
Now we’ll head downtown. First, though, get to Old Dixie Highway. The Colonial Estate is private, but you can see it from the road. A good zoom lens will allow you to get some decent photos.
The streets in downtown Kissimmee run at an angle, not directly north-south and east-west. It can throw you off for a bit until you adjust. Most of the buildings below are in the boundaries of the historic district. An interesting non-building is the Monument of States, which is built from material accumulated from all the states. Well, except Alaska and Hawaii, since it was built after the Pearl Harbor attack. The buildings are clustered in different spots. Look at the map and decide where best to strategically park. It’s a very busy downtown, but I’ve not had problems finding decent parking. (see Google map)
- Colonial Estate (2450 Old Dixie Highway) (NRHP)
- Kissimmee Historic District (Roughly bounded by Aultman Street, Monument Avenue, Penfield Street and Randolph Avenue) (NRHP)
- Old Holy Redeemer Catholic Church (120 North Sproule Avenue) (NRHP)
- First United Methodist Church (215 East Church Street) (NRHP)
- First Presbyterian Church (15 Church Street) (AGFHA)
- Kissimmee Valley Gazette-Jordan Norris Building (113 N Stewart Avenue) (AGFHA)
- Winn-Hunter House (215 N Orlando Drive) (AGFHA)
- Osceola County Courthouse (Bounded by Emmett, Bryan, Rose, and Vernon Streets) (NRHP)
- Captain Clay Johnson-Steffee House (404 S Vernon Avenue) (AGFHA)
- Billy Makinson and Nathaniel Carson Memorial (200 Lakeshore Boulevard)
- Monument of States (Monument Avenue and Johnston Street)
- I.M. Mabbette House-Lakeview Lodge (104 Monument Street) (AGFHA)
- Walking trail
I’m including the Lanier House, but it’s very out of the way, and Street View doesn’t show much there. It’s possible that the place is gone. Or possibly moved to the Pioneer Village and Museum. There is a Lanier House there. I’d check there first. (see Google map)
- Lanier House (1964 Ham Brown Road) (AGFHA)
Get back on US 441 and head east. You’ll go under the Turnpike, and now you’re in St. Cloud. There was a sugar plantation here, all remnants of which are gone. There’s only a historical marker near city hall to commemorate its existence. When you get to Florida Avenue, take a left. You’ll be able to get to all the sites of interest off this road. Go to the lakefront first and see the Sam Lupfer-Davidson House, and other older houses near it. There’s also a nice city park on the lake if you want to stretch your legs and take in a view of the lake.
Head back down Florida Avenue. There are nice old homes along here too. There’s probably more on the side streets. Consider taking one or two and see what turns up.
When you get near downtown, follow the map below. Like Kissimmee, the historic stuff is clustered. You can see everything by only parking in three or four places. There are also older looking buildings which might entice you to wander further. Another place I’m surprised isn’t a historic district. Or two. (see Google map)
- Sam Lupfer-Davidson House (711 Lakeshore Blvd) (AGFHA)
- St. Luke and St. Peter’s Episcopal Church (813 10th St) (AGFHA)
- Livingstone Memorial Church-First United Methodist Church (1025 10th St) (AGFHA)
- Hamilton Disston Sugar Plantation Marker (South side of 9th St., between New York and Massachusetts Aves) (AGFHA)
- St. Cloud Hotel (1004 New York Ave) (AGFHA)
- St. Cloud Heritage Museum (1012 Massachusetts Avenue)
- Grand Army of the Republic Memorial Hall (1101 Massachusetts Avenue) (NRHP)
- First National Bank Building-Golden Age Club (1200 New York Ave) (AGFHA)
- Walking trail
Get back on US 441. If you want to get to Lake Okeechobee by an off-route, head back west until you get to Canoe Creek Road, then head south. You’ll think you’re never going to see the end of civilization, but eventually you will. Then there’s only miles of road and trees, with a blip of the modern world when you drive over the Turnpike. You can’t get lost. There’s a trailhead for the Sunset Ranch Interpretive Trail, if you feel like hiking for a while. Keep going south and you’ll pass over the Turnpike again. You’ll be in Kenansville, then back on US 441. (see Google map)
- Sunset Ranch Interpretive Trail (1003 State Road 523)
But I’ll extol the virtues of Kenansville later. If you choose not to go down Canoe Creek Road, head east on US 441 when you’ve finished exploring St. Cloud. Before you know it, the buildings will thin out. You’re heading into rural Osceola County. When you reach the US 92/US 441 split, you can keep on US 92 and see the Holopaw State Forest. It doesn’t look that big, and I’m not sure what facilities it has, if any.(see Google map)
- Holopaw State Forest (Holopaw State Forest)
Now you’re going down a road that most casual tourists don’t see. Since the Turnpike parallels US 441 most of the way until it jogs east on its way to Miami, only locals go down this road. Or those going to the city of Okeechobee. Even those probably take the Turnpike at least to Yeehaw Junction. This is why I like this section of US 441. It’s so completely opposite of what you’ll see on it going through Orlando. And the speed limit is close to that of the Turnpike, so you’re not losing that much time.
This is agrarian Florida. More specifically, cattle country. People outside Florida (and even inside) think citrus and tourism are our major industries. But cattle ranching is still right up there with the rest. You’ll see prairies with roaming cows all the way down. This is what much of Florida was like a hundred years ago. Development is encroaching, but I think it’ll stay concentrated on the coast and around urban areas like Orlando. Unless something radically changes, I expect a lot of this part of the state will look the same a hundred years from now.
It’s almost 70 miles until you reach Okeechobee. There are a few picnic spots on the side of the road, if you need to pull over and rest. But there are some small towns along the way, with more amenities, if needed.
The first is 18 miles from Holopaw. I mentioned it earlier; Kenansville. I think it started out as a train stop. I don’t believe it was ever a bustling metropolis, but it did appear to be a small thriving community. Enough so to have a bank and rather large cemetery. You’ll find them all on Canoe Creek Road. Nearest are the old bank and the Heartbreak Hotel. The rest are to the west. The old cemetery is the farthest, just before you get to the Turnpike overpass. There’s a modern convenience store on the corner, where you can get knoshies to tide you over until you get to the big city of Okeechobee. (see Google map)
- Piney Woods Inn-Heartbreak Hotel (1350 South Canoe Creek Road) (AGFHA)
- Kenansville Bank (1351 South Canoe Creek Road) (AGFHA)
- Kenansville School (795 South Canoe Creek Road) (AGFHA)
- Post Office (795 South Canoe Creek Road) (AGFHA)
- Kenansville Cemetery (199 South Canoe Creek Road)
- Walking trail
Now one of my favorite places, for name value. Another of my many travel interests are unusual Florida place names. I’ve visited DeFuniak Springs, Wewahitchka, Two Egg, and Zolfo Springs. I’ve been to Venus and Jupiter. The towns, not the planets.
But right up there is Yeehaw Junction. The few times I went this way to or from Miami, I stayed on the Turnpike. I saw the exit for Yeehaw Junction and always wondered what it was like. Finally, I took the plunge.
Not much to see, honestly. A company was trying to do residential development here, but didn’t get too far. The economy and gas prices would likely have killed the project, but malfeasance got there first.
Can’t say I’m really sorry. Don’t let Yeehaw Junction become the next Clermont (now more of a bedroom community for Orlando).
If you’re going to south Florida, and want to save some money, get off at this exit and take SR 60 to Vero Beach and catch I-95. It’s about 20 miles, with a 65 mph speed limit almost the whole way.
Back to the Junction. You’ll drive over the Turnpike, and it’s only a couple miles further. Right at the intersection of US 441 and SR 60 is the furthest south NRHP in Osceola County, the Desert Inn. It’s decades old, started as a place for cowboys to stop on cattle drives across this part of the state. I don’t know how much it’s still used by cowboys, but bikers seem to like it, which is always a good sign. I got a sandwich there, and it was pretty good. So if you didn’t get any food before this and are feeling hungry, give it a try. If you need gas, there are a couple of stations east on SR 60 on the way to the Turnpike. One of them is also a Stuckey’s. (see Google map)
- Desert Inn and Restaurant (5570 South Kenansville Road) (NRHP)
The next major stop after this is Kissimmee Prairie Preserve State Park. There’s a northern entrance, supposedly, but I’ve not been that way. I’m going to direct you to the southern entrance.
It’s easy to get to. Drive to the back of beyond, turn right and go past the middle of nowhere, hang another right until you get to BFE, keep going and there you’ll be.
Not much of an exaggeration, really. It’s about 18 miles down US 441 to the turnoff for the park. Another 10 miles will get you to a small collection of streets and mobile homes, where you’ll have to drive real slow. I think 25 mph. Signage directing you to the park is good, so if you’ve followed it, you’ll reach the entrance gate. There’s no ranger station there, it’s an honor system park. You still have even more miles of dirt road to traverse before you get to camping areas and the turnoff for the ranger station and museum.
This is the park I would send people to if they complain about how overdeveloped Florida is. There’s getting away from it all, really getting away from it all, then there’s coming here. I’m not much for camping, but I may spend the night here someday. The view of the night sky here is supposed to be spectacular. I’d say it’s the furthest away place from city lights in Florida. A cool fall evening here would be something else.
From here, you can go along the road on the map indicated and see the remnants of Fort Basinger. Not much more than a historical marker, really. The few buildings left are on private property, far from the road.
Or you can go all the way back to US 441 and head south for 15 miles until you reach Okeechobee. Not a lot to see either way except prairies. But if you’re like me, and enjoy the journey as much as the destination, you’ll be happy whichever one you choose.
That’s it, y’all. See you on the road!
Route length: 95 miles