Trail Snapshot


22.5 miles. Some sections of trail do not as of this writing connect. See review. The Cross Seminole Trail runs from its connection with the Seminole Wekiva Trail at Heathrow in the north, to Lake Mary, Longwood, Winter Springs, Oviedo and then turns south west towards Goldenrod and it's connection with the Cady Way Trail. The Cross Seminole Trail is a paved recreational trail that has been designated as one of Seminole County's Showcase Trails because of its length, beauty, and accommodation of various users. The section of Cross Seminole Trail from downtown Oviedo to the I-4 Pedestrian Bridge in Lake Mary has been designated as part of the Florida National Scenic Trail, a 1300-mile trail running from the panhandle to the Everglades.



Outdoor Travels Rating:

2.75 out of 5 bikes.

Thumbs Up and Down

Thumbs up:

  • Connects with two other Orlando area trails
  • Several places to eat or stop for refreshments
  • Big Tree Park section is very pretty
  • Thumbs down:

  • Traversing the areas between the disjointed sections can range from confusing to horrible.
  • Nuts & Bolts


    The Cross Seminole Trail runs from its connection with the Seminole Wekiva Trail at Heathrow in the north, to Lake Mary, Longwood, Winter Springs, Oviedo and then turns south west towards Goldenrod and it's connection with the Cady Way Trail. Orlando, Florida


    Lake Mary Trailhead has full facilities including nice restrooms, parking, water and a restaurant.
    Other Trailheads include: Big Tree Park and Black Hammock.

    Access and trailheads:

    Lake Mary
    Parking for the trail is available at the intersection of Rinehart Road and Lake Mary Boulevard at the large Lake Mary sign and fountain.
    Black Hammock trailhead
    From Downtown Orlando, take the East-West Expressway toll road to SR 417 (the Central Florida Greeneway – toll road). Follow SR 417 north to SR 434. Exit on SR 434 and take a left, heading west for about 750 feet. The trailhead is on the left.
    146 Division Street Oviedo, FL 32765




    Biking, skating, walking, jogging


    Seminole County Trails & Greenways 520 West Lake Mary Blvd., Suite 200 Sanford, FL 32773 (407) 665-2093

    Maps Links and Photos

    Maps and Links:

    Seminole County Trail Map

    Map My Ride Map

    Useful Links

    Trail Photos:

    Lots of great photos to give you a good idea of what riding here is like!

    Cross Seminole Trail

    Where the Crossings Trail connects to the Seminole - Wekiva Trail (note I-4 bridge in background)

    Very cool I-4 pedestrian bridge

    At the Rinehart Road crossing (the other side of the bridge)

    Riding along Rinehart Road

    Facilities at the Lake Mary Trailhead

    Bridge at the Lake Mary Trailhead

    Bridge at the Lake Mary Trailhead

    Pretty scenery

    Bridge over 92 and 15

    Heading through Big Tree Park

    Where it - DOH!

    Looking back at the "end" at Big Tree Park

    Looking at Old Sanford Oviedo Road from the "end"

    Bridge over 419 and 434

    Passing under Florida 417 Toll Road

    Howell Creek Trestle

    Access in Oviedo right after Smith Street

    Where the trail resumes after crossing Red Bug Lake Road

    Heading towards Cady Way

    At the southern terminus / connection with Cady Way Trail


    Cross Seminole Trail

    Orlando, Florida
    A key link in the Orlando Trail Network
    Dana Farnsworth, Outdoor Travels

    The Cross Seminole Trail in Orlando, specifically Heathrow, Winter Springs, Oviedo and then onto Goldenrod is as of October, 2009 a nearly completed 22.5 mile multi use trail that serves as one of the backbones of the Orlando biking trail network. That said, the sections that are not yet complete can be challenging to navigate. More on that later.

    The initial commitment to this trail was obvious. Beginning at Heathrow, a large expansive bridge spanning eight lanes of I-4 has been finished for several years. This bridge connects the norther beginnings of the Cross Seminole (or Crossings trail as this section is known) with the Seminole Wekiva Trail (reviewed on this site) on the west side of the bridge. Also the full service trailhead at Lake Mary Blvd. and Rinehart Road was completed early on and features parking, nice bathrooms, a small hot dog shop and a nice bridge that spans West Lake Mary Blvd. So far, it looks like the initial commitment was a good indicator of progress. In 2004 only two non connecting 4 mile sections existed. Within a few short years many miles of asphalt has been laid and several bridges have been built. If I had a guess I would think that within the next few years, the gaps that exist now will be ironed out and all will be completed.

    Moving along... Here's a brief run down of the Cross Seminole Trail beginning from the north at Heathrow. The trail is very diverse and it's personality varies from urban to wilderness to industrial and about everything in between.

    A great beginning

    North from the bridge at Heathrow heading south. After 2 miles, you'll arrive at the lake Mary trailhead, which is a good place to start, as the 2 miles leading up to it run along the side of Rinehart road and are of little interest unless you are using it to shop or commute. THe Lake Mary trailhead is full service featuring restrooms, food and water. Here you'll cross over West Lake Mary Road using a nice overpass. The Cross Seminole trail then briefly follows Greenwood Blvd. and then into a power line easement that runs between a residential neighborhood and then passes under Greenwood Blvd. via a cool and inventive underpass.

    Abrupt confusion

    After exiting the underpass, there is approximately another half mile along the power line easement and BAM! The trail ends abruptly at Green Way Blvd. Standing there and looking across Green Way Blvd. one can see more power lines, behind a brick wall. I am assuming that eventually the trail will continue along the easement in the future, but as of late October, 2009, it stops. If one didn't know better, it appears to be the end of the road. So ends the initial 4 miles of trail that was built first and is often referred to as the Crossings Trail. To access the next section of trail, requires traversing the largest gap that currently exists in the Cross Seminole Trail. Facing south, turn left onto Green Way Blvd. There is a widened sidewalk, but honestly I was freaked out riding against traffic on a widened sidewalk, so I got in the road. Follow Green Way Blvd. east approximately .5 miles and take a right (south) onto Longwood Lake Mary Road.

    Of note, the large sidewalk continues on the west side of the trail. Curiously, it currently is not marked as being the Cross Seminole Trail if one is heading in this direction. On the return, there are signs directing a rider. At any rate, I believe that the widened sidewalks are pretty dangerous. If you are comfortable riding on the road, I suggest doing so.

    Continuing south on Longwood Lake Mary Road, you'll travel approximately 1 mile. You'll then come to the crossing with North Ronald reagan Blvd. This is a busy intersection, and crossing over requires two crossings. One of Longwood lake Mary Road and the finally crossing Ronald Reagan. Once across, you'll see a widened sidewalk that is clearly marked as being the Seminole Wechiva trail. Use this sidewalk.

    Into the wild

    Almost immediately after accessing the sidewalk on Ronald Reagan Blvd. The trail makes a right into Big Tree Park and transforms itself from a widened sidewalk back into a proper multi-use trail. The park is aptly named as large tall trees shade a really lovely portion of the trail. Watch out for tree debris on this section. I ate pavement when I pegged a large seed pod / nut thing. Keep both hands on the wheel through here. A cool bridge spans 600 and 17 and then continues on through the forest. A little after mile 7 the Cross Seminole Trail crosses over 419 and continues along Park Road / Osprey Trail before turning south (right) and begins following a power line easement through the middle of thick Florida forest. The fun ends all too soon.

    Confusing connections, industrial wasteland and the need for a cyclecross bike...

    As you probably guessed, the trail comes to another abrupt "end". The trail, once in what is probably the prettiest section of the Cross Seminole Trail, now stops at the beginning of what looks to be a nasty, dirty, ugly semi-abandoned industrial area. Dismounting our bikes we walked across a sandy section that spans the end of the trail to what is Sanford Road. Please note, that unless you are familiar with where the trail goes, this traverse is very confusing. You'll want to turn left (your only choice) onto Old Sanford Oviedo Road. The surface is sandy, gravel strewn broken blacktop (no fun). Next, turn right (south) onto Wade Street and take that to 419. At 419, take a left (east) a short distance to the entrance of Layer Elementary School. Turn left into the driveway for the school. The trail, not too soon, resumes on your right. I'm not sure how, if ever these sections will connect.

    Hit the trail

    This next section is also a very nice stretch of trail, in that there are just a few intersections over the next couple of miles. Soon the trail passes by Winter Springs high School, turns back into the woods briefly and then crosses over 434 and 419 via a nice bridge. The next several miles are wooded and mostly intersection free. Of note, the Howell Creek Trestle offers up a pretty view of Howell Creek. The trail then passes under the Florida 417 Toll road and the Eastern Beltway as you enter a residential section on your way to the small town of Oviedo.

    The Oviedo connection

    The bad news? The trail is once again, non-contiguous here. The good news? It's easy to find your way, even if the locals I asked for directions didn't have a clue. First off, there isn't a trailhead in Oviedo, well, not one near the trail that I could find. If you want to access the trail from here, you'll need to park in a parking lot of one of the businesses there or at the address that I found after my ride (listed in the Trailheads above). Back to the trail. At the "end" in Oviedo at North Central Avenue and Myrtle Street, take a right (south onto North Central Avenue (the main drag in Oviedo) and ride a short distance. Once you see Smith Street on your right, you'll see a sidewalk heading west (right) into some trees - that's the trail. There must have been some access issues here a the trail soon resumes again. Continuing on through a wooded suburban area for a bit, you'll arrive at your next navigational challenge.

    County Road 426

    Once again, and all too soon, the trail morphs into a sidewalk that intersects West County Road 426. there are no signs here directing a rider where to go. The way to go is left (south) onto West County Road 426. There is a bike lane on 426 as well as a sidewalk. As always, I recommend the bike lane. Pretty soon, you'll arrive at the prodigious intersection of Red Bug Lake Road, West Mitchel Hammock Road and 426. Apparently the project to build a bridge over this intersection has, as of this writing, been put on hold, due to 4-5 million dollars not sitting around the county courthouse. The Cross Seminole Trail begins again after the intersection on the west side of 426. At this point it runs in front of a shopping center that has several food choices if you so desire.

    Onto the Cady Way!

    The next few miles are fairly uninteresting from a recreational / scenic standpoint, but very important from an access / commuter standpoint. Paralleling 426 for a bit, the trail heads towards it's intersection with the Cady Way Trail. Once the trail turns away from 426, it begins to parallel Florida 417 Toll before passing under it and continuing to an intersection with Tuskawilla Road, Within a mile, the trail ends (or begins) at the intersection of Howell Branch Road and 426 (Aloma Ave.). The Cady Way trail is accessible on the southern side of 426.

    Overall Impression

    The Cross Seminole trail is at once frustrating and interesting. An important piece of the Orlando trail network, the Cross Seminole trail connects with the Seminole Wekiva Trail in the north and the Cady Way in the South. The Cady Way connects with the Little Econ Trail. The plan is coming together nicely. However, the news isn't all good. Finding one's way from one section to another can be challenging to the uninitiated. Plans are in the works to fix most of these ills and create an easier transverse. I for one am looking forward to our next update. Oh, once again, watch out for those rogue tree nuts - they lead to sporadic bouts of road rash.

    Sierra Trading Post