Island hopping: 42 years of riding to the end of the road

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Light rain pelts the windshield on my Harley-Davidson Ultra Classic as I cross over emerald and turquoise waters. The only land I can see for miles are a few mangrove clusters here and there.

I’m riding across the Seven Mile Bridge in the middle of the Florida Keys, with the Gulf of Mexico on my right and the Atlantic Ocean on my left. Off in the distance, a veil of water falls from a grey cloud, but I can see the road for miles, off into the horizon, and it looks like we’ll skirt around it, leaving us relatively dry.

I’m on the 42nd Annual Phil Peterson's Key West Poker Run, where winning at the card game really does come in second to the ride itself. The event benefits many local charities in the Keys, along with diabetes research, and the winner gets either a new Harley-Davidson Street 500 motorcycle or six grand in cash.

rust bikeI’ve been making this annual rally for a few decades now, with only a few exceptions. My doorstep is only a short hour away from this wonderful trek on the Overseas Highway, so I also find myself down here in the Keys other times. But there’s something more exciting about riding to the end of the line with some 30,000 other like-minded spirits.

The run was established in the early years as a Saturday and Sunday event to help the Key West economy at its slowest time of year. Recently, the organizers have spread out the opening day to Thursday, in an effort to avoid the traffic jams that ultimately develop with that many people trying to get around at the same time, and to help the upper Keys cash in a little on the action.

The run has grown so popular, I regularly see tags from up and down the eastern seaboard, and this year, the award for the farthest rider went to a fellow from Sturgis, S.D.

sidecar on Seven Mile Bridge

Key LargoI usually hang out until Monday, to avoid the crush to get home, and this year my riding buddy and I took advantage of the early start time by staying in Key Largo for the first night, which also happens to be the first stop in the run. There’s something about crossing that first 20 miles from the mainland to Key Largo that immediately puts you in quite a different place, both physically and mentally.

On this ride, by the time I hit the third stop my card game is already over, as I carry a king, a three, and a six, all unsuited. I know the eventual winner is going to be holding either a royal flush or four face cards. My riding companion and I are undeterred, as I can still win our side bet for dinner over whoever has the best hand.

Duval Street in Key West

Once at our destination in Key West, the main drag (Duval Street) has been shut down for motorcycle travel and parking only. Vendors line the side of the road hawking the usual stuff of interest to bikers — just like any other major rally across the country — except there’s quite a bit of island–themed stuff added to the mix.

There’s plenty of lodging within walking distance of the fun, so it’s easy to park the bike for the night and then enjoy all the island has to offer to the fullest. With a bike show, plenty of great restaurants, the famous Key West nightly sunset celebration that is part circus and part live performance art, and a plethora of bars and live music to meet your tastes, no matter which way they may lean, it’s no wonder this event has grown steadily over the years.

Key West bike show

I draw my last card, a queen, and I yell enthusiastically, “Hey, I got nothing!”

In the same tone, the volunteer says, “Hey, you’re right!”

Ah, but that’s the beauty of this thing. I had a great ride, helped out a good cause, and now I’m getting a beer and listening to the sounds of the island. Winning isn’t everything.

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