Along the Upper Keys portion of the Florida Keys Overseas Heritage Trail, you’ll run into a lot of locals.
This is the most densely populated portion of the Florida Keys, with the largest number of hotels and resturants as well.
So this part of the trail is more of a connector between communities and services than a scenic ride, particularly since ocean views are limited to glances from bridges at a couple of passes.
You’ll need to be alert along this ride because of the amount of traffic crossing the bike path and the spots where it dumps you into the bike lane.
The trail takes you by several state parks and lesser-known local preserves, and a couple of natural attractions worth seeing.
At both the beginning and end of this ride, there is a bike path on both sides of US 1, the better for you to avoid crossing the highway except at traffic lights.
Our resources for exploring the area
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Location: Islamorada to Key Largo
Length: 26.8 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.
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.
When visitors think of Islamorada, they think of Upper Matecumbe Key. But in fact, Islamorada spans across several islands, with Upper Matecumbe the most densely populated and busiest.
From the south end of the island, you have the option of following a bike path up either side. Both have lots of driveways and side roads to cross.
Changing sides of US 1, however, can be an issue. So if you start your ride north from the Upper Matecumbe Key Wayside, follow the bike path on the bay side.
In the first mile on the bay side, the trail leads you past two little-known but lovely natural areas preserved by island residents, the Key Tree Cactus Nature Preserve and Green Turtle Hammock Preserve.
Both have interpretive nature trails that showcase native plants and habitats, plus parking. They are gated so mind the hours posted at the gate.
Passing a massive outfitter, Bass Pro Shops, you reach the public library and behind it, pretty Library Beach Park with a beach along Florida Bay at 1.6 miles.
If you’ve ridden up the ocean side of US 1, a significant stop at this mileage point is the Hurricane Monument.
It is a burial crypt and WPA-era memorial which honors the hundreds who lost their lives during the 1935 hurricane that destroyed the Overseas Railroad.
The island has many hotels, and you’ll see the entrances to most of them along the ride.
Within the next half mile on the ocean side, the bike path passes the Keys History & Discovery Center, one of the larger history museums in the islands.
At 2.2 miles, the bike path ends at Southwinds Park on the ocean side, and you’re directed into the narrow bike lane along northbound US 1.
On the bay side, the bike path narrows to sidewalk width around this point. Watch for a break in the traffic to switch sides of the road.
The bay side also has the Historic of Diving Museum, 3 miles along the route, and a large Publix supermarket, with the path, at this point a sidewalk, ending at Park Rd soon after.
In the northbound bike lane, cross the Whale Harbor Channel bridge, which has a nice view towards the east.
The next key in the islands of Islamorada is Windley Key. The west side of the island is a state park, but the east side is quite busy.
The bike lane continues past a marina and hotels up to CR 905, where a sidewalk parallels the bike lane in front of a classic marine attraction, Theater of the Sea.
While narrow, the sidewalk is asphalt and suitable for riding. It broadens to a bike path as soon as it is past the attraction.
The trail stays within a median east of US 1 between the old and new highways, passing the entrance to Windley Key Fossil Reef Geological State Park at 5 miles.
When the bike path ends, resume the northbound bike lane to cross Snake Creek on the US 1 bridge.
The view from the bridge is the broadest clear glimpse you get of the Atlantic Ocean along this ride through the Upper Keys.
It’s a little hectic when you first get onto Plantation Key as there is a weigh station for trucks that the bike path slips in front of in a very narrow lane. Watch for exiting traffic.
For the next five miles, it’s a ride in the bike lane. While John darted across US 1 to get a photo at the giant Keys lobster in front of the Rain Barrel, it’s rare that the road is clear enough to do so.
If you do, however, there is a bike path on the bay side that starts just north of the lobster and can be followed up to Founder’s Park, a good stop for cold water and restrooms.
That bike path continues north up the bay side of US 1 to Plantation Blvd, mostly bounded by a large residential area.
If you stay on the ocean side, it’s worth slipping onto Old US 1 (SR 4) as soon as it appears. It lets you parallel US 1 but avoid being so close to traffic. And it’s far less busy.
It also has a marked, dedicated bike lane along most of its length, but on the southbound side of the road.
You can pretty much follow it to the north end of the island, exiting at a turnoff north of the traffic light at Plantation Ave to rejoin the US 1 bike lane.
Plantation Tropical Preserve is on the opposite side of US 1 here. The traffic light provides a way to connect to it for parking purposes.
Reaching the bridge over Tavernier Creek at 10.8 miles, enjoy one final look at the Atlantic Ocean to the east.
The bike lane leaves Islamorada and continues into the town of Tavernier, paralleled by a concrete sidewalk.
Once beyond the mangrove flats, you enter another residential and commercial area, with a large shopping center on the bay side at a traffic light at Ocean Blvd.
The bike lane simply ends here. Your options are to ride in the traffic lane or on the adjacent concrete sidewalk.
There is a good bit of cross-traffic here to keep alert for, as well as pedestrians. The bike lane returns just a block past the Driftwood Trailer Park, with the sidewalk paralleling.
At 12.6 miles, you reach the traffic light for Burton Drive. Here, the bike path resumes in the intersection.
Join it here, or you get stuck with a guardrail between bike lane and bike path north of this traffic light.
While the bike path still parallels US 1, you have the satisfaction of riding by a dense tropical forest for over a mile.
The north part of Tavernier is partly residential but largely protected east of the bike path as part of the Florida Keys Wildlife & Environmental Area.
It is a wild area with just one cleared and landscaped spot where a sign calls your attention to the preserve.
When the commercial and residential appears again, you’ve entered Key Largo. On this part of the island, hotels are on the bay side and some cafes are on the ocean side.
After another stretch of tropical forest, the trail leads you across a crosswalk on US 1 to the median at 16.4. There is no light and traffic is 60 mph, so cross carefully.
The ride up the median has northbounders facing southbound US 1 traffic on the west side of the median, which begins wooded but turns commercial.
Just a quarter mile past a convenience store is the REEF Marine Conservation Center at 18.3 miles. Nicely shaded, it has picnic tables and interpretation of native species.
Within the next mile you pass several restaurants and cafes. The median ends at Atlantic Blvd, one of the busiest intersections in Key Largo.
You have a choice of paths here, on either the bay side or the ocean side. Both crossings are at the traffic light with a crosswalk. We recommend the ocean side.
At 19.6 miles, a right at Laguna Ave by the Holiday Inn leads back to YMCA Park, a large city park with ample parking, restrooms, and water fountains, should you need them.
After a handful of hotels and businesses, there is another nice long stretch of tropical forest adjoining the trail.
Just north of it is Hibiscus Lane at 21.1 miles, with Friendship Park immediately to the right, a closer-to-the-trail stop for restrooms and water.
Past the park is a busy entrance with traffic light to a large shopping center with a Publix supermarket and a library.
The next road on the right after the shopping center leads back to Key Largo Kampground, another rare commercial campground that welcomes tent campers.
Passing Hobo’s Cafe soon after, there is a lengthy stretch of residential with many small side streets cutting across the trail.
When the side streets stop and the tropical forest begins, the split-rail fence signifies you’re along the edge of John Pennekamp Coral Reef State Park.
Cross the entrance road into this popular park at 22.6 miles. More residential streets start again north of the park.
The bike path bumps you into US 1 to cross the Adams Waterway, then resumes north of it. On the bay side is another campground with tent camping, Kings Kamp RV Park.
A mix of residential incursions into the tropical forest follows, with some nice scenic stretches of dense tropical hammock as the trail nears its end.
Rowells Waterfront Park is on the bay side where Esther St is on the ocean side at 24.5 miles. A handful of commercial establishments front the bike path.
Once you’re past the Key Largo School, the dense tropical hammock takes over the east side of the trail again.
At 26.3 miles, the trail reaches Garden Cove Rd. It’s here that US 1 curves west and Card Sound Rd continues due north, paralleling the bike path.
John rode the last half mile along Card Sound Rd, but it appears the bike path may be extended to meet the state park at its terminus.
The Florida Keys Overseas Heritage Trail ends at 26.8 miles at the parking area for Dagny Johnson Key Largo Hammock Botanical State Park.
The park has a small parking area. Walk a tenth of a mile up the paved path inside the park archway to find picnic tables and a composting toilet.
Cyclists continuing along the East Coast Greenway will follow Card Sound Rd north from here. It’s narrow and rough in spots but nowhere near as busy as US 1. There is a toll bridge.
Fill up on water before doing so, since there is none until Florida City, 26 miles north. That convenience store just before the state park is the last chance stop for water.
South to north trailheads along the bike route. Click on any icon above for directions.
A limited amount of parking is available at preserves along this part of the trail. Do not assume you can park overnight at these locations. They are gated and have hours posted.
Unlike the Middle and Lower Keys, you will find no trailside pulloffs along the Florida Keys Overseas Heritage Trail through the more densely populated Upper Keys.
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.
Upper Matecumbe Key has the most options for day use parking, with four parks and the Upper Matecumbe Wayside. With the exception of the wayside, the parks have very limited parking.
We used Green Turtle Hammock Preserve as a staging point since it had a larger parking area, picnic tables, and a portalet, plus a nice hiking trail to explore.
On Windley Key, the only parking option is the state park. There is a fee, and it has very limited operating hours and is not open every day of the week.
On Plantation Key, Founders Park on the bay side is your best bet. It has a large parking area fronting US 1 next to a visitor’s center, plus restrooms and drinking water.
Two smaller preserves on the bay side also offer a limited amount of day use parking: Plantation Hammock Preserve and Plantation Tropical Preserve.
Tavernier is home to Old Settlers Park at Albury Blvd, but we don’t list it on the trailhead map simply because the parking spaces are posted “for park use only.”
Harry Harris Park is a beachfront park in Tavernier that is 1.3 miles off the trail at the east end of Burton Drive. A bike lane runs up one side of Burton Dr.
The REEF Marine Conservation Center made a sweet rest stop along the ride and might allow cyclists to park for day use.
Two city parks, the YMCA Park by the Holiday Inn and Friendship Park, are on the ocean side and have restrooms and water fountains. Parking at both is free.
The bayside Rowells Waterfront Park tends to be much busier because of its beach on Florida Bay.
For a fee, parking is available at Pennekamp State Park, but it’s less costly to park at the actual end of the trail at Key Largo Hammock, where exact change is needed for the iron ranger.
|0.0||Upper Matecumbe Wayside bayside|
|0.6||Keys Cactus Preserve bayside|
|0.9||Green Turtle Hammock Preserve trailhead|
|1.6||Library Beach Park / Hurricane Monument|
|3.7||Whale Harbor Channel|
|4.4||Theater of the Sea|
|5.0||Windley Key State Park entrance bayside|
|6.9||Founders Park & Plantation Hammock Preserve bayside|
|10.6||Plantation Tropical Preserve bayside|
|13.2||Florida Keys WEA|
|16.4||Cross US 1 to median|
|18.3||REEF Marine Conservation Center|
|19.5||Atlantic Blvd. Crosswalks to bike paths on both sides of US 1|
|19.6||YMCA Park 0.1E restrooms & parking|
|21.1||Friendship Park restrooms & parking|
|22.6||John Pennekamp Coral Reef State Park entrance|
|24.5||Rowells Waterfront Park bayside parking|
|26.8||Northern Terminus @ Key Largo Hammock|
Learn more about the Florida Keys Overseas Heritage Trail
Along the Route
Visit these parks and trails along this ride
On a wild sliver of Upper Matecumbe Key, footpaths wind through a rockland tropical hammock where a rocky crevice emits sulfur fumes and you must beware of crocodiles near the mangroves
Preserving a patch of tropical forest surrounding a quarry opened in 1908, Windley Key Fossil Reef Geological State Park showcases the uniqueness of the Florida Keys in both botany and geology, with vast slabs of coral frozen in stone awaiting your inspection.
Adjoining Founders Park on Plantation Key, Plantation Hammocks Preserve showcases some of the Florida Keys most interesting flowers under a generous canopy of well-established tropical trees.
Six miles offshore, the view is beneath the waves. It’s Molasses Reef, the most accessible living coral reef in the United States, a slice of the Caribbean in the Florida Keys. And it’s the main reason that John Pennekamp Coral Reef State Park exists.
Articles from rides and explorations along this trail
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.
On the Florida Bay side of Tavernier, a paddling trip to Toilet Seat Cut will have you laughing your way down the channel, as contributor Tamara Scharf explains.
Although John is a native Floridian, our research trip to South Florida became an opportunity for him to see many natural “firsts” in Florida that most people have on their life lists.