Overseas Heritage Trail


Following the path of Henry Flagler’s old railway, the Florida Keys Overseas Heritage Trail provides a way for cyclists to ride the 106 miles from Key Largo to Key West. More than 70 miles of the trail have been paved, and in fact, new portions were marked and completed while we were there.


You can hardly ask for a more beautiful ride with the water in sight a good part of the ride. Most of the trail runs parallel to US 1, and while there are dedicated bridges for bikes, pedestrians and fishermen in some portions, it’s necessary to share the road in other places, making for some dangerous encounters with traffic.


We never had any intention of riding the full length of the trail, 106 miles (one way) is way more than I can manage. And while we saw a few cyclists riding the full distance, there are too many sections which are much too dangerous. When roading sharing is required, the bike lane is often narrow and filled with debris. However, what worries me the most are the drivers…residents in a hurry to pass the slow moving tourists, trucks and cars pulling boats and campers, eighteen wheelers rushing to make deliveries, tourists gawking at the fishermen reeling in their catches, not to mention the harsh, sometimes, blinding sun. We witnessed a woman drive off the road into the water. What if there had been a person on a bike?

Despite these challenges, we had a WONDERFUL time riding the Overseas Trail, riding almost 60 miles over the course of three days.

Our first ride was truly a destination ride as we unloaded our bikes and rode the last five miles to Mallory Square in Key West to not only enjoy a bike ride but to avoid the traffic and hassle of finding a parking space.


The next day we took a short ride from our campsite in Long Key State Park to see the sunset, all on a paved trail off the side of the road. (It’s also the place where we watched a car skid into the water the next morning.)

The fifteen mile ride on Marathon was the most enjoyable as it was all off road and took us out on the old 7 Mile Bridge, which is dedicated to bikes, pedestrians and fishermen. The final leg of this ride ended on Sombrero Beach, which may be the best beach in the Keys.

Without a doubt, the most beautiful ride was from MM71 to MM81, twenty miles round trip, past gorgeous houses and clear blue-green water with lots of boats filled with fishermen. Unfortunately, this section requires cyclists to share the road with traffic across three bridges. And even though the shared lanes were wider than on most bridges, I still held my breath while crossing.

Our final ten mile ride on Long Key included a 2.2 mile span across the water, separate from traffic, but being a Saturday morning, packed with fishermen. No problem! I can dodge their casts much easier than vehicles.


The Florida Keys Overseas Heritage Trail provides riders with spectacular views, and it’s one I’d ride again…but, only  by skipping the parts I feel are unsafe, and only by riding in the cooler months. We were lucky to have perfect weather with temperatures in the 70s all week. Since there’s very little protection from the sun, I can’t imagine riding in the heat of the summer.




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