It’s not often that the two of us join a group ride, but Sunday was an exception.
John had gotten a personal invitation from his old friend Curtis – someone he’d shared adventures with when they were both Boy Scouts in the 1960s and 1970s – who was putting on a bike trip in Osteen.
Since the starting point would give us an opportunity to try a piece of bike path neither of us had done, plus net me more miles on the East Central Regional Rail Trail, we decided to tag along.
Especially since Curtis had billed this as an easy ride, and expected two new-to-cycling riders to be a part of the group.
We circled Beck Ranch Park, looking for the starting point. Since the widening of SR 415 ended back when we lived in Sanford, we saw a constant flurry of construction and activity across from Reed Ellis Road, so we never stopped.
It had been a good dozen years or more since I last hiked at Brickyard Slough, part of Lake Monroe Conservation Area.
So it was quite a surprise to see that the conservation area had its own big parking area, large enough to accommodate not just a crowd, but horse trailers as well.
While we waited for the other cyclists to arrive, it rained. I dove back into the car and waited it out.
By the time everyone was ready to go, we did one more lap around the park before taking on the bike path paralleling SR 415. We’d use it as a connector up to the East Central Regional Rail Trail.
I’m not all that fond of bike paths that sit just a couple of feet away from a highway, and the gray skies did not make the ride compelling.
Still, it felt a lot safer than riding in the bike lane, and traffic turning at intersections did stop for us.
We whizzed past the Osteen Diner, which was pretty busy on a Sunday morning, and continued on to meet the East Central Regional Rail Trail where it came down off the bridge, just off Railroad Street.
It was about this time I heard Joe mention to John that his surname was Osteen, which is why he’d driven halfway across Central Florida to try this ride.
John had cycled this piece of the ECRRT – which is a portion of the statewide C2C – when we lived in Sanford. It was my first time on it.
After we exited Osteen, where the path goes behind a handful of homes, I was appreciative of the forested corridor.
I knew Maytown Road was near, but the only time I noticed it was when the trail jogged out towards it to make its way around homes whose drainfields were plopped right on top of the old railroad right-of-way.
The ECRRT ended, as it did several years ago, at Guise Road. That was somewhat disappointing, as we’d hoped that by now it had been extended towards Maytown.
No such luck. Curtis wanted to check on a campsite at Hickory Bluff Preserve, so we all rode down Guise Road to reach the preserve.
The preserve was one I’d discovered back when I was working on Five Star Trails Orlando, and had visited it several times since to hike out to the bluffs on the St. Johns River.
As I’ve been nursing a bit of a knee sprain that I picked up on our last trip, I opted not to ride off-road on the loop out to the river, which the group planned to do.
Instead, John and I turned around and headed back, figuring I could take my time and not stress my knee too much. As we returned to the ECRRT, the skies cleared up, making for a pleasant ride back into Osteen.
Once we were within sight of Beck Ranch Park, I noticed that my knee was starting to bother me. We’d racked up more than a dozen miles already.
Given the beautiful blue skies, I suggested to John that he continue up the SR 415 bike path to the St. Johns River.
That way, he could both get a bit of sprinting in, and take a look at what – from the highway – appeared to be an underpass that led the bike path from the east side of 415 to the west side.
Reaching the top of the Douglas Stenstrom Bridge, John was rewarded with quite a view towards Lake Monroe, showcasing the wetlands of the conservation area and the meandering path of the river itself.
As we’d thought, the bike path did a little twirl under the bridge to reach the west side.
Strangely, the path simply ends at Celery Avenue, the first turnoff after you cross the bridge into Seminole County.
A broad sidewalk continues, but it doesn’t appear to be meant to be a bike path, unlike the one extending to Osteen.
We’re curious if any connectivity is planned up to the Riverwalk in Sanford, or if this was just a way to get cyclists over to Celery Avenue, which has far less traffic on it than SR 46.
Returning back over the bridge and to the trailhead, John finished up with a little over 17 miles for the ride. We packed up and headed to the Osteen Diner, arriving just in time to grab a table for the group so we could enjoy a post-ride meal.
If you’d like to try a gentle adventure like this with a group leader who knows their stuff, check into a Meetup Group near you!
- Michael Crotty Bicentennial Park - November 3, 2026
- A.J. Henry Park - November 1, 2026
- Okeeheelee Nature Center Trails - October 22, 2026