Which way do you turn out of Trailhead Park?
The city calls the spot at Rinehart Road and Lake Mary Boulevard the unofficial entrance to Lake Mary, and the description holds up once you're standing there. There's a fountain, a sign, a Planet Smoothie counter, and the start of a paved trail that eventually covers more than 20 miles of Seminole County. What the sign doesn't tell you is that the trail changes character almost immediately depending on which way you go, and the difference matters more than the mileage number ever will.
Head north and you're on pavement that runs beside Rinehart Road with almost no tree cover, closer in feel to a long sidewalk than a nature trail. Head south and within a handful of blocks you're under a canopy that won't break for miles, moving through a string of parks that most people never connect to this one trailhead. Same pavement, same trail name, two different mornings.
Two Directions, One Trailhead
| Direction | What it actually feels like | What's along the way | When it works best |
|---|---|---|---|
| North, toward I-4 | Exposed, parallels busy Rinehart Road, little shade | Crosses the pedestrian bridge over I-4 to the Seminole Wekiva Trail, continuing toward the Sanford Riverwalk | Early morning, before the sun clears the roofline |
| South, toward Greenwood Lakes Park | Wooded, shaded, threads through quiet residential streets and public parks | Greenwood Lakes Park, Big Tree Park, Soldiers Creek Park, Black Hammock Trailhead, Central Winds Park | Any hour, thanks to the canopy |
The county's own measurement puts the trail at 23 miles from the Aloma Avenue and Howell Branch Road intersection in Winter Park up to the pedestrian bridge over I-4 in Lake Mary. That's the number most maps quote. But the trail doesn't stop at that bridge. Riders who cross it and keep going pick up the Seminole Wekiva Trail and can continue on toward Sanford's Riverwalk and Lake Monroe Wayside Park, adding roughly five more miles beyond the county's official count. From Trailhead Park, you're standing close to the midpoint of a corridor that runs from one end of Seminole County to the other.
What the City Already Fixed
The northern stretch's lack of shade isn't a secret to the city that maintains it. The section of trail that starts right at Trailhead Park, officially named the Rinehart Trail, has been redesigned with a fitness course, new landscaping, and rest stations along the way. None of that solves the shade problem outright. Trees take decades the city doesn't have. But the additions read as an acknowledgment: if the corridor can't offer tree cover for another twenty years, it can at least give you a reason to stop moving for a minute, a bench in the sun instead of no bench at all.
Trailhead Park itself backs this up. Three miles of walking trail radiate from the parking area, along with picnic tables, a playground, and the Planet Smoothie stand that serves as the closest thing to a finish line this end of the trail has. Restrooms and water fountains are on site, which matters more on the exposed north stretch than it would under tree cover, where the heat builds faster and the next stop is farther away.
The Shaded Half Has a Story of Its Own
Turn south from Trailhead Park and the trail passes Greenwood Lakes Park before curving near Lake Mary High School and continuing into Big Tree Park in historic Longwood. This is where the trail earns its reputation among people who've ridden the whole thing.
Big Tree Park is named for what's inside it. The Senator, a bald cypress estimated at 3,500 years old, stood there until it was destroyed by arson in 2012. A clone taken from its tissue, now called The Phoenix, has been planted near the playground. The tree that carries the "Big Tree" title today is Lady Liberty, a bald cypress estimated at 2,000 years old. A boardwalk leads visitors past both trees, the living one and the charred remains of the one that came before it. It's not a detour built for tourists. It's a park that happens to sit on the trail's route, which means anyone riding south from Lake Mary passes it whether they planned to stop or not.
From Big Tree Park the trail continues into Soldiers Creek Park, then toward the Black Hammock Trailhead in Winter Springs, where a concrete pedestrian bridge carries the path over State Road 434. From there it passes Central Winds Park, described by longtime trail cyclists as the county's premier public park, before threading into Oviedo and eventually meeting the Cady Way Trail at the Orange County line. The entire southern run stays largely wooded and away from major roads, which is the reason experienced riders consistently rate it above the northern stretch for anyone not in a hurry.
The Exposed Half Still Gets You Somewhere
The northern route out of Trailhead Park doesn't get the same praise, but it isn't pointless. It's the fastest way out of Lake Mary on two wheels or on foot without touching a car, and it's the only direction that connects to Sanford. Cross the I-4 pedestrian bridge and you're on the Seminole Wekiva Trail, which continues toward the newly extended Sanford Riverwalk and ends at Lake Monroe Wayside Park. For anyone training for distance, or anyone who just wants to see Lake Monroe without driving there, this is the direction that gets you across county lines fastest.
The tradeoff is exposure. Longtime riders describe this segment bluntly: a wide, sun-exposed path running alongside a busy road, with little relief until the bridge. It's a stretch better suited to early morning or late afternoon than the middle of a Florida summer day, and the rest stations and fitness equipment near Trailhead Park make more sense once you've felt what the next four miles are like without them.
Two Different Saturday Mornings in the Same City
Trailhead Park isn't the only outdoor institution in Lake Mary running on a Saturday schedule. A few minutes away by car, Central Park behind Lake Mary City Hall hosts the Lake Mary Farmers Market every Saturday from 9 a.m. to 1 p.m. The market runs year round and includes produce, baked goods, plants, honey, handmade jewelry, and pet treats, and it's dog friendly, same as the trail. The Lake Mary Historical Museum sits across the street, close enough to fold into the same stop.
Neither of these replaces the other. The trail rewards showing up before the market opens, when the north stretch is still cool and the south stretch is quiet. The market rewards showing up once the sun is higher and you're ready to be around people instead of moving past them. Two different rhythms, both native to the same square mile of the city, both starting from a parking lot a few minutes apart.
What ties the two halves of the trail together isn't the pavement. It's that Lake Mary sits at a hinge point on a much longer system, close enough to Sanford to reach it by bike and close enough to Big Tree Park's four-figure-year-old cypress to reach that too, all from one lot at Rinehart and Lake Mary Boulevard where the smoothie stand marks the start of both trips.
Jen King has spent more than twenty years learning which corner of Lake Mary to be on at which hour, including which direction to point a bike out of Trailhead Park before the July sun makes the decision for you. If a morning on this trail turns into a bigger conversation about what it's like to live along it, reach out to Jen King.
