Hiking the Eastern Loop Around Orlando on the Florida Trail

This suburban and urban section is an iconic section of the Florida Trail. It gets maligned quite a but it was one of my favorite sections because of its uniqueness. It is not a road walk through a city as its reputation might suggest.

Welcome to Suburbia

The next twenty-five miles are no longer in the wilderness. It is a stark contrast to the bulk of the trail so far, even including the long desert road walk.

The next day or two provides ample cell signal, convenience stores, grocery stores, restaurants, and many other businesses of interest to the hiker. There are hotels that the trail passes right by further north in Lake Mary, or a quick hitch or Uber ride at the southern end in Oviedo or centrally in Winter Springs. There is even one campsite near the middle of the city walk.

The majority of it is on rail trails or other dedicated bike paths, but some of it is on normal sidewalks. All of it has some sort of dedicated non-motorized footpath. From the State Forest to the north to the State Park to the south, it is not a road walk. It follows most of the Cross Seminole Trail which spans the entire Seminole county. Even when it is just a widened sidewalk along a road, it is an officially dedicated and purpose-built foot and bike path.

This entire section is within 12-15 miles of the downtown center of Orlando. Orlando is not a small town, and you would expect just a tangled mass of four-lane city streets. But this is not the case. There are many of these large feeder highways that you cross over on dedicated pathways most of the time, but sometimes they are conventional crosswalks. it is true suburbia, except for the section in Lake Mary near Interstate 4, which I consider urban. It is barely urban, though.

Starting From Oviedo

As you exit the Little Big Econ River State Park, you are deposited at a trailhead that begins a sidewalk hike just east of the small town of Oviedo, FL. This town is not known for much, but just ten miles south is the University of Central Florida, one of the fastest-growing Universities in the state, partially due to its location close to the Kennedy Space Center and all the tech companies located in the area.

The trail here is on the sidewalk. And you are also introduced to the first convenience store of this suburban walk within the first mile. For me, that means an ice cream sandwich stop. It also means paying attention to traffic as you have to cross many roads to get to the city center.

Leaving the city center of Oviedo on the dedicated Cross Seminole bike and pedestrian trail.

Once you reach the city center, there are many interesting places to visit. For me, that meant the pizza shop right across the street from the trail. There is also a public library, and public restrooms right at the park that you are walking through. Just a few blocks away are the Post Office, a few restaurants (including an ice cream shop), and a convenience store.

The trail here at the park now transitions from a sidewalk to a dedicated path for bicycles and pedestrians as it bends around the lake. As you cross the main north-south road, the path now enters a wooded area in the middle of neighborhoods. Sometimes the houses are so close you are peering into their backyards, and other times you can see only woods but can hear the trappings of suburban life. Aka lawn mowers and cars.

Since the trail is in suburbia, it will pop out to road crossings every quarter mile or so. Unlike many other trails in suburban areas, this one forces all the cars to a complete stop with posted stop signs. I am used to no signage, maybe a crossing painted on the street, maybe a sign for the cross traffic warning drivers of pedestrians, or maybe a blinking sign. The traffic is usually given the right of way, but this trail prioritizes pedestrian traffic. That was a nice and unexpected touch.

This is pretty good hiking. It’s dry, there are interesting things to look at, and the cars must stop at every intersection.

There are many little creeks to cross, and one of them at Howell Creek is quite large and has an elaborate boardwalk, trestle, and resting area built high over the water below. It has a suburban wilderness feel to it. I would be spending a tremendous amount of time on this trail if I lived in the area.

It’s a fancier trail when it becomes an elevated path above the creek below.

Winter Springs

It is hard to tell where Oviedo ends and Winter Springs begins, but it could be at the overpass for the Seminole Expressway. The personality of the trail definitely changes here. No longer is it a woodland nestled between houses. The houses give way to multi-family housing, and the trail makes its way next to the road.

The first large complex you come to is labeled as “luxury condominiums.” The condominium part is easy to figure out, but the luxury part is a bit harder. What is the difference between a standard condominium and a luxury one? They looked nice. But I like my tent better.

Even when the trail is next to a road, it’s still a designated non-motorized trail.

There is an outdoor plaza here, but I did not bother to go off-trail to explore the shops. There is also a large baseball complex. But the public restrooms are the highlight of the eastern part of Winter Springs for me. Never underestimate the power of a flushing toilet.

In the middle of this section, the trail turns away from the road and enters the Spring Hammock Preserve. This is a heavily wooded section that has a surprise for those who do not like to stay in hotels. Enough said about that. This area was busy with folks on bikes and runners. It is a popular area.

After you exit the preserve, then it becomes more suburban again, but with a few convenience stores and dining options. I was really looking forward to stopping at Mama’s Empanadas, but she closed the business the month before I arrived. Mama’s is no longer, but a new restaurant is opening in the same location, and there was a Subway sandwich shop next door, so I did not go unfed.

This intersection crosses CR 427, one of the few large roads you cross via crosswalk instead of a pedestrian overpass. This also marks the end of Winter Springs and the transition into Lake Mary.

Lookie, lookie - I found Trucker Bob. Or rather, he found me.

Lookie lookie – I found Trucker Bob. Or rather, he found me. You can almost see the disappointment on my face as in the background is the former Mama’s Empanadas which closed less than a month ago. Trust me, I am not crying… yet.

Lake Mary

Since Orlando is just one giant mass of suburbs, it’s hard to tell when you officially enter Lake Mary. Maybe there is a sign that I missed, but when you hit Lake Mary High School, you have definitely arrived.

Right next to the high school is a park and a library with outlets, Wifi, and restrooms. They have some shade trees that provide ample shade and grassy areas for a quick nap. The FarOut app shows the trail staying on the sidewalk, but the real Seminole trail actually wanders off the road and snuggles in between the library and the park. Not that it really matters much.

A critical mistake was made just before this area. I dozed off and missed the turn to go to the high school and kept going about a quarter mile past the turn. It would have been easy to bushwhack through the neighborhood (on roads, not people’s backyards) to get back on track, but I turned back instead. This same mistake was repeated again later when I missed the turn to hit the suspension bridge over Interstate 4.

The trail turns to follow the high-tension power lines right of way. You are close to neighborhoods and lakes, and there are no trees anywhere near the power lines, obviously. So this is a very sunny section, but there are interesting things to look at.

There is a tunnel to go under Greenwood avenue and a neat overpass for West Lake Mary Boulevard. At the latter, there is a huge shopping area with many restaurants and other businesses. There is a Planet Smoothie that hikers love, but I stopped at Jason’s Deli for a quick snack.

One of the fancier pedestrian overpasses. This is the one over Lake Mary Boulevard.

This time we get to go under the road via a tunnel.

And the crossing I have been waiting for… the suspension bridge over Interstate 4.

The section along Rinehart road is probably the closest thing to an “Orlando City hike” that people would fear. It is still the Cross Seminole Trail, but it is just a very wide sidewalk along the side of a very busy street. But one thing to make up for the unpleasantness is they have bottle-filling stations about every quarter mile.

This is where I missed another turn. I was supposed to cross the street just before the Postal center, but I kept on going past it. I could have bushwhacked again, but then I would have missed the suspension bridge over I-4. No Bueno. That is one of the reasons I took the eastern route around central Florida. I backtracked and made my pass over I-4 on the coolest bridge on the entire trail.

Once you cross the bridge, you are in another commercial area, but it has a more urban feel to me. This is where you will find several large hotels, including the Lake Mary Marriott. There are several places to eat in this area, too, and another large grocery store as you are exiting Lake Mary.

The trail then begins to revert back to how it started in this suburbia. It becomes a dedicated path near roads, then slowly into woods, then it dumps you back out onto a road so that you can cross the Wekiva river.

The trail returns to a woodland oasis in the city as you get closer to the Wekiva river and Seminole State Forest.

This section has been completely rebuilt in the last few years. it used to be just a sidewalk or road walk across the river, but they have built a really nice dedicated path the entire way until you hit the entrance road to the Seminole State Forest. I was impressed.

Pick One Emotion

I need to pick either anticipation or surprise.

This is one stretch I have wanted to hike for thirty years. It is one of the reasons I chose the eastern route around central Florida instead of the western route that goes closer to my home. It’s hard to talk yourself into a section hike that just goes through a concrete jungle.

Or at least I was told it was a concrete jungle. It started out that way and was that way in the middle of Lake Mary, but the rest of the trail was quite pleasant and really fun.

I was surprised that so much of the trail was on a dedicated paved path. I was surprised that for much of the trail through neighborhoods, the pedestrians had the right-of-way and not crossing vehicles. I was surprised at the number of overpasses or tunnels that completely avoided all of the busy and crowded roads I knew spewed out across this area from Orlando. I was surprised at how heavily wooded some stretches of the trail were. And I was surprised to find a campsite right in the middle of it all.

I expected convenience stores and restaurants. In fact, I think I expected more. That was somewhat of a surprise. I didn’t expect to miss two turns and have to backtrack a quarter of a mile each time. That surprised me.

And I was surprised at how much I enjoyed this stretch through town. I don’t fear it at all. I’m not sure I want to make a section hike out of it or anything, but I would gladly hike it again.

So I think surprise wins my vote for the emotion I experienced in this section of the trail. I wonder what the emotion would be if I hike it again now that I know about all of the surprises that await me.

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Comments 3

  • Jacqueline : Mar 10th

    Dear Jim,

    Wonderful and very interesting blogs!

    I would really like to do this eastern loop/Orlando walk. I searched for a map of this route. Could you tell me where on the internet I could fine one or maybe email one to me?

    Thank you and joyful hiking to you!


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