Of the three segments we’ve broken the trail into, the Middle Keys give you the biggest “wow” panoramas, but these are usually from the bike lane on US 1 on highway bridges.
While there are nice stretches of bike path on most of the islands, accessing them northbound means a lot of darting across US 1, which can be difficult to impossible at times.
You’ll ride many road miles through this section, most notably over highway bridges, the longest of which is the Seven Mile Bridge.
The four restored railroad bridges along this segment provide incredible views, but the bridges are also very popular with anglers who set up for the day on them.
Along the route, there are many stops worth making, from natural attractions and parks to museums, cafes, and quirky roadside statues.
Striking a balance between ocean views and the busy corridor of Marathon, this segment also has many more options for lodging than in the Lower Keys.
Our resources for exploring the area
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Location: Spanish Harbor to Islamorada
Length: 43.6 miles linear
Land manager: Florida State Parks
Open daylight hours to pedestrian and bicycle use. Hikers should use sunscreen and insect repellent. Leashed dogs welcome. Please pick up after your pet.
Class 1 ebikes (pedaling required) are permitted on state trails but other motorized transport is banned on bike path segments.
Because this is an island hopping route, sun and wind play a factor in your enjoyment of the ride. Check wind direction and speed before deciding which direction to ride, or to ride at all.
Facilities are a bit more limited on the other islands but not like in the Lower Keys. Lock up your bike when leaving it unattended at restrooms and trailheads.
Read our information about poisonous plants in Florida before you ride. Along this trail are forests where both poisonwood and manchineel trees are present. Avoid touching them.
Florida’s Toxic Trees
Southeast Florida is home to two poisonous trees, the poisonwood and the manchineel. Learn how to recognize them so you don’t get too close, and find out how truly dangerous they are.
Leaving the gate of Bahia Honda State Park, traffic determines whether you backtrack the half mile towards the bridge to use the underpass, or cross US 1.
You can also use the US 1 bike lane northbound, which we did since you are forced over to it anyway at the north end of this island.
Across the length of the state park, which occupies the island, the bike path is on the bay side. For a stretch, a fence runs along it to separate it from the cabin camping area.
Then the mangrove-lined edge of the island isn’t at all far from the trail. This portion washed out during Hurricane Irma but should be repaired.
At the north end of the island, the trail comes to an abrupt end at a closed bridge, with a split-rail fence adjoining the pulloff area.
Cross US 1 (no underpass provided, use caution) and get in the northbound bike lane for the bridge crossing to Ohio Key.
As seen from the bike lane on the Bahia Honda-Ohio Channel bridge, the waters in the channel are a gorgeous aquamarine.
Again, the bike path is on the bay side so it’s no help northbound, and the next historic bridge along it is closed. So stay along the US 1 bike lane across Ohio Key.
Cross the next highway bridge over the Ohio-Missouri Channel to Missouri Key. The bike lane is also on the bay side across this island.
Stay with the bike lane, since the bike path hits yet another closed bridge up ahead. Cross the Missouri-Little Duck Key Channel on the highway bridge.
The bike path starts up again on the bay side. Unless you plan to stop at the Seven Mile Bridge monument stay on the bike lane. Veterans Park is on the right and gives you a rest stop.
We swapped over to the bike path for the monument and to take a hydration break. At 3.2 miles, the path comes right up into the wayside park adjoining both the old and new bridges.
While you can walk or ride out on the old span, it doesn’t go through. Cyclists must use the bike lane on US 1 and yes, the bridge stretches 7 miles over the ocean.
Some cyclists opt to have a friend meet them here for a hop to Marathon to avoid the bridge. Traffic is high speed along it but the bike lanes are wide.
The ride is windy, not just from the breezes off the water but from passing traffic, and fully exposed. There is no bailout or shelter along it.
There is a significant rise in the middle of the span to allow larger boats passage beneath.
It’s quite a view from the top, but easy to pick up too much speed on the downhill towards Marathon.
Along the old bridge, which is broken in the middle, is Pigeon Key. It has bunkhouses from when the Overseas Railroad was built and is now a historic site.
Reaching shore, there’s an immediate traffic-based decision to make. If no traffic is approaching, quickly cross US 1 to the bay side, where the bike path resumes to cross Marathon.
If it’s busy, a new underpass was under construction last we checked and should be complete. It adds 0.9 mile via Knights Key Blvd back under the bridge to the bay side.
The bike path stays on the bay side across busy Marathon, the largest community in the Middle Keys. Watch for cross traffic and parked vehicles on the trail.
Passing the 7 Mile Grill, a popular restaurant at 10.9 miles, the trail is crossed by many entrances into businesses.
Some of these are museums and nature-based attractions you may be interested in visiting, such as the Marathon Turtle Hospital.
Slightly north of this sea turtle rehab facility is today’s first opportunity for a quirky Keys photo op at the shark in front of Shady Palm Art Gallery.
At 12 miles, you cross 33rd St. A city park is a block west at the bay and has restrooms adjoining the boat ramp.
Marathon Community Park is a very large park almost a half mile farther along, but it’s on the opposite side of US 1. You see it across the highway just before the giant tropical fish.
In front of Crane Point Hammock – an excellent nature attraction with miles of interpretive trails through a historic site – is a traffic light.
It’s an important one for connections. To the east, Sombrero Beach Blvd leads 2 miles to a park on the beach, with a bike path paralleling it out there.
A Publix shopping center on that side of US 1 is where the Miami-Dade Transit bus stops.
Other major shopping and a couple of parks are on that far side of US 1 too. This is one of the rare spots where pedestrians can cross with a crosswalk and light.
The path continues north from the traffic light in front of more driveways and roads. One of these belongs to Herbie’s, a great place to try conch fritters, a Keys delicacy.
By 13.9 miles, the bike path makes a long arc in front of the Marathon International Airport.
North of the passenger terminal and parking lots, a sign brought attention to a vintage aircraft museum right next to the trail, the EAA Museum.
The airport ends, and businesses begin again. A nature attraction is along the bike path just before Vaca Cut bridge, the Florida Keys Aquarium Encounter.
Vaca Key is part of Marathon but less crowded. Once over the bridge at Vaca Cut, you’ll pass numerous business entrances along the bike path.
Island Fish Company is the last restaurant in Marathon. Pass that and the Vaca Key Wayside, and the trail becomes a pleasant ride into Curry Hammock State Park.
This next section is called the Grassy Key Trail, and stretches 4.4 miles north from Vaca Key Wayside past another trailhead. It’s a good destination for a short ride.
Grassy Key Trail
A pleasant piece of the Florida Keys Overseas Heritage Trail that is entirely a paved bike path, the Grassy Key Trail runs 4.4 linear miles through Curry Hammock State Park.
Along it, there’s a shaded rest stop and benches with an ocean view, as well as a nature trail and access to Curry Hammock State Park across US 1, which has a campground.
At the end of this segment through a tropical forest corridor, a sign points you back out to US 1. Cross the highway to rejoin the bike lane northbound.
Since Hurricane Irma, we’re not sure if the mom and pop motels and restaurants on the ocean side of Grassy Key rebuilt.
But a little over a half mile north of where you rejoin US 1 is the Wreck & Galley Grill, followed by an enormous dolphin statue in front of the Dolphin Research Center.
Jolly Roger RV Park, a rare private campground that allows tents and has cabins to rent, is also on the bay side.
A half mile north of that complex, the bike path resumes on the ocean side, so you can easily segue over to it from the bike lane.
At 23.8 miles you reach the next of the historic railroad bridges, the Tom’s Harbor Channel bridge.
The bike path leads you across it and then evaporates. Back to the bike lane on Duck Key, pass the entrance to Hawks Cay Resort.
Soon after it the bike path resumes over the Tom’s Harbor Cut railroad bridge, ending at the other end of the bridge at Conch Key.
Rejoin the US 1 bike lane, passing by the Bayview Inn before you get to a resumption of the bike path on the ocean side as it approaches a paved parking area.
Here, 26.4 miles into the ride, you come to the second longest bridge in the Florida Keys, the Long Key Viaduct.
When it was completed in 1912, it was the longest bridge in the world and an engineering marvel. It remains the longest concrete arch bridge in the Keys.
Restored for the trail to cross in 2001, it clocks an impressive 2.3 miles over the ocean. Most anglers cluster at the ends near the parking areas.
That enables you to pick up some speed in between or just stop and savor the surroundings, a stunning ocean crossing by bike without any vehicles nearby.
At the north end of the bridge, the paved parking area is frequently busy and we’ve encountered drivers parking right atop the bike path.
After passing some residences, the path continues on the ocean side through Long Key State Park. Like at Bahia Honda, a fence separates the trail from the fee portion of the park.
Crossing the park entrance drive at 30.7 miles, continue north along the trail into the town of Layton, passing the pretty Lime Tree Bay Resort.
Early Western novelist Zane Grey made this island his home for 15 winters, penning many stories at the Long Key Fish Camp while enjoying fishing the surrounding flats.
The trail stays on the ocean side of the island until it gets to its north end, where there is a crosswalk to the bay side.
Unless you are stopping at the large Channel Five parking area on the bay side, don’t cross the road. Join the US 1 bike lane to go up and over the highway bridge.
It’s a sweeping descent onto Craig Key, where the bike path resumes on the bay side, necessitating crossing US 1 once you can.
While the Channel Five railroad bridge remains broken in two pieces, the location of the bike path seems to point to its restoration someday.
There is very little land on Craig Key, and only a couple of homes. Most of the ancient limestone reefs are under water.
So the views across US 1 out into the flats behind the reefs along the Atlantic Ocean are especially beautiful as you cross this island.
At 35.9 miles, you reach a small parking area and then the bike path takes you across the historic Channel Two railroad bridge.
This is another long bridge, more than a mile span. Since there are parking areas at both ends expect to encounter many people fishing or sightseeing along it.
Crossing Channel Two brings you into Islamorada, a collection of islands governed as a municipality. This is the southernmost island of the chain, Lower Matecumbe Key.
Along its scenic southern end, the views are nice as the bike path leads you past Anne’s Beach, a county park on the opposite side of US 1.
A quarter mile later, you cross the first road on the island, which leads into the gate of Florida Sea Base, a Boy Scouts of America high adventure camp for sailing.
Once the bike path reaches the convenience store at 37.6 miles, it’s time to keep alert for vehicles as it crosses driveways and roads leading to neighborhoods.
The trail joins the old highway paralleling US 1 for a stretch in front of small Keys-style hotels and residences along the bay side.
A lane is marked along the road as a bike lane, but don’t be surprised to find vehicles parked on it.
After the road and then the residences end, the bike path continues along the bay side, dumping you out into a residential side road along US 1 that leads into Robbie’s Marina at 40.7 miles.
This is one of the toughest places to cross US 1 back to the northbound bike lane, but it must be done to get across the next several islands, as there are no old bridges remaining.
There is a yin and yang to the remainder of the ride. As you cross these bridges and causeways, the views are outstanding across the channels and the water.
They are the last place along the trail that you’ll see panoramas like this, looking off to Indian Key and Lignumvitae Key.
At the same time, all of the bridges must be crossed in the US 1 bike lane. Traffic tends to be heavy here much of the time.
While there are bike paths across the causeways on both sides of the highway, vehicles commonly park atop them, forcing you into the highway.
The final bridge is a short hop onto your destination, Upper Matecumbe Island, within view of Bud N’ Mary’s Marina.
The Upper Matecumbe Wayside is only a half mile north of the bridge, but it’s on the opposite side of US 1. Crossing this highway is especially tricky on this island.
If you aren’t wrapping up your ride at the wayside, stay on the ocean side of the island and pick up our narrative of the ride with the Upper Keys section.
Bike paths run up both sides of US 1 on the island, the better for local residents to get around.
South to north access points along the bike route. Click on any icon above for directions.
A limited amount of parking is available at pulloffs adjoining the historic bridges along this part of the trail. Do not assume you can park overnight at these locations.
For overnight or multi-day trips, make arrangements in advance to leave your car at a state park or a business you’ll be patronizing along the route, such as a hotel.
Between Marathon and Islamorada, Miami-Dade Transit runs route 301, the Dade-Monroe Express. Bikes are welcome. Link to their schedule is at the bottom of the page.
Buses should be hailed at their designated stops: Key Largo (MM 98), Tavernier (MM 87), Islamorada (MM 74), and Marathon (MM 50).
You can use both Miami-Dade Transit and Key West Transit to go the length of the Florida Keys, as both routes overlap at Marathon.
See our Lower Keys section for Key West Transit details.
Bahia Honda State Park
There is a fee for day use parking at Bahia Honda, but there are restrooms and a snack bar on site, as well as camping: reserve it well in advance.
Check with the park about leaving your vehicle here overnight for a fee during a multi-day ride.
Little Duck Key Wayside
This bayside wayside is between the old and new Seven Mile Bridge, so you’ll find the original bridge monument here. The bike path ends here before the bridge.
Veterans Park is on the ocean side of the approach to the Seven Mile Bridge along the US 1 bike lane. It has restrooms and parking.
Marathon Community Park
Large park complex on ocean side of US 1 with restrooms, potable water, multiple day use parking lots.
Crane Point Hammock
Museum, nature center, and gift shop at Sombrero Beach Blvd in Marathon on the bay side adjoining the bike path. Entry fee to museum and trail complex.
Key Vaca Wayside
Large paved parking area adjacent to the trail on the bay side. Primarily used by boaters for launching into Florida Bay.
Grassy Key Trail trailhead
Trailside parking for a handful of cars along US 1 bay side in Curry Hammock State Park, a mile south of the park’s main entrance.
Curry Hammock State Park
Parking lot adjoining picnic area and restrooms inside Curry Hammock State Park, 0.5 mile east and across US 1 from the trail. Entry fee applies.
Tom’s Harbor Parking
A paved parking area adjoining the bike path oceanside as it accesses the south end of the historic Tom’s Harbor railroad bridge.
Conch Key Wayside
Paved parallel parking adjoining the bike path as it comes up to the Long Key Viaduct crossing.
Long Key Viaduct
A paved parking area is oceanside along the bike path where it comes off the historic Long Key Viaduct, a 2.3-mile bridge that the trail crosses. It’s a worthwhile destination on its own.
Long Key State Park
Day use parking and restrooms are available at Long Key State Park at a parking lot 0.3 mile from the bike path. Entry fee applies.
Channel Five Parking
A large paved parking area adjoins the south end of the historic Channel Five Railroad Bridge on the bay side. This bridge does not go all the way through.
Channel Two Parking
A large paved parking area adjoins the north end of the historic Channel Two Railroad Bridge, which the trail crosses.
Often mobbed on the weekends, Robbie’s Marina features boat rentals, a restaurant, gift shops, and kayak rentals for paddling over to Indian Key.
If you’ve never seen a tarpon, stopping here to feed them is a tourist tradition. Contact the marina about potential overnight parking.
Upper Matecumbe Wayside
At the south end of Upper Matecumbe Key, this wayside park has picnic pavilions along an unpaved strip of land on the bay side. We end our Middle Keys mileage here.
|0.0||Bahia Honda State Park main entrance|
|1.6||Ohio-Bahia Honda Channel pulloff|
|2.2||Ohio Key pulloff|
|3.1||Veterans Park (ocean side)|
|3.2||Little Duck Key Wayside (bay side)|
|3.3||Seven Mile Bridge|
|10.4||Marathon bike path (bay side)|
|12.4||Marathon Community Park (ocean side)|
|13.2||Crane Point Hammock / Sombrero Beach Blvd|
|16.2||Florida Keys Aquarium Encounter|
|17.2||Key Vaca Wayside parking|
|18.5||Grassy Key Trail trailhead|
|19.4||Curry Hammock State Park main entrance (ocean side)|
|23.7||Tom's Harbor parking area|
|24.1||Duck Key pulloff|
|24.7||Tom's Harbor Cut pulloff|
|25.0||Conch Key pulloff|
|26.2||Conch Key parking|
|26.4||Long Key Viaduct|
|28.8||Long Key Viaduct parking area|
|30.7||Long Key State Park main entrance|
|34.0||Channel Five parking area|
|35.0||Channel Five north parking area|
|35.9||Channel Two parking area|
|36.4||Channel Two north parking area|
|36.8||Anne's Beach (ocean side)|
|42.7||Tea Table Key|
|43.6||Upper Matecumbe Wayside (bay side)|
Sombrero Beach Trail
A side path running 2.1 miles east in Marathon, this paved path leads to one of the nicest beaches in the Florida Keys, with picnic areas and restrooms.
At the southern tip of Marathon, Sombrero Beach offers beachgoers a natural strand and an easy beach walk within sight of the Keys’ largest lighthouse.
Learn more about the Florida Keys Overseas Heritage Trail
Florida Keys Overseas Heritage Trail
Spanning from Key West to Key Largo, this 108-mile linear state park corridor is an island-hopping slice of tropical paradise along the former route of the Florida Overseas Railroad
Along the Route
Visit these parks along this ride
Bahia Honda State Park
Long known for its natural beaches, Bahia Honda State Park continues to heal after the ravages of Hurricane Irma stripped much of its tropical vegetation
Crane Point Hammock
Part native, part cultivated, Crane Point Hammock is 63 acres of tropical hammock in the heart of Marathon, with one of the most extensive trail networks in the Florida Keys.
Curry Hammock State Park
Bring your binoculars for fall birding at Curry Hammock State Park, where migrating raptors cruise overhead by the hundreds following a major flyover route.
Long Key State Park
Spanning shore to shore across much of its namesake island, Long Key State Park offers a bounty of botanical wonders across a variety of rare Florida Keys habitats.
Indian Key Historic State Park
The original seat of Dade County, settled in 1836, lies in limestone ruins swaddled in a tropical forest within sight of US 1, but offshore. Indian Key takes a little planning to visit, but is well worth the journey.
Lignumvitae Key Botanical State Park
Wrapped in a dense blanket of mosquitoes, Lignumvitae Key Botanical State Park is one of the United States’ most significant botanical treasures, a virgin tropical forest home to more than a thousand lignum vitae trees.
Articles from our rides and explorations along this trail
The Florida Keys, Revisited
Nine months after Hurricane Irma, we headed to the Florida Keys to see how both the infrastructure and the natural areas are healing. Here’s an overview of what we found, from Key West to Key Largo.
Indian Key: An unusual ghost town
John takes a trip back in time with Florida Keys historian Brad Bertelli to discover the layers of history found on Indian Key, once the county seat of Dade County
Paradise, Palms, & Mosquitoes
My first exploration on the hiking trails of Marathon lead to thatch palm hammocks: the Curry Hammock Nature Trail at Curry Hammock State Park, and the trails of Crane Point Hammock, including the beautiful Palm Hammock Trail.