Keep Fit: Riding My Bike From Southampton to Montauk

For better or worse, I like to think of a Hamptons summer as a challenge. With a maximum of three months of perfect beach weather, it’s very necessary to deliberately enjoy each day. I’m not a hyper-planner, but there are certain things—like a bicycle trek to Montauk or walking outside barefoot—that can only be enjoyed when the weather is warm.

The ride from Southampton to Montauk was born, as these things tend to be, out of boredom before I owned a car. Bound by my bicycle—which I still maintain is the least frustrating way to travel around the Hamptons—I was craving a chance to get out of Southampton. In the days before iPhones became ubiquitous fixtures, my brother and I turned to handy MapQuest to figure out a route that would avoid Montauk Highway for as long as possible. With printed directions in hand, we set off. The trek has become a yearly sojourn, paying homage to the beauty of the Hampy Hamps while subsequently allowing us to enjoy a few hours at The End.

Though I travelled with my iPhone on Sunday, it was strictly for musical interludes along the Napeague Stretch. The ride through the back roads has since become second nature, a delicate balance to keep the beach to your right and the highway to your left.

Sunday’s sun was shining, but there was a soft, cool breeze that—thankfully—didn’t let up. We started out our excursion—29.2 miles, a little under four hours—in Southampton Village, hugging Hampton Road before meeting up with the “Cobbs”—Cobb Road and Little Cobb Road, which, not surprisingly, bring us by a few corn fields.

It’s so rare that I associate Hamptons travel with leisure—too often I’m fighting traffic in a rush to get somewhere or fuming about the guy who tried to cut me off. But when you max out somewhere around 10 mph, and that’s on a downhill, you’re forced to simply enjoy the East End’s raw nature. A favorite stop on the journey are those sights that remind you of how “small town” it really is out here. (Specifically, I recommend checking out Sagg Bridge and Main Street, Wainscott; and then trying to convince people that you’re actually quite close to New York City.)

By far the most difficult part of the trip is the Napeague Stretch. Six-or-so miles of flat Flattsville with little in view to break up the trip. The Napeague ride is followed by a Sophie’s Choice-type decision that makes you immediately regret thinking of how “hard” the Stretch is—to take Old Montauk Highway or New Montauk Highway? New Montauk offers 1.5 miles uphill followed by 1.5 miles downhill, and a decently wide shoulder. Old Montauk is all about the rolling hills, virtually no shoulder and a Podunk sidewalk that sporadically begins and ends. But it’s on the ocean, and we opted to go for the views this time. Cresting that final hill and seeing the hamlet nestled between Fort Pond and the Atlantic is one of the greatest feelings in the world. We coasted into the business district, immediately falling in sync with Montauk’s beachy vibe.

The bike here is best served with a subsequent dip in the ocean. We casually tossed around a Frisbee, grateful for its red color and float-ability, before retiring to our beach towels.

Our rest was short-lived, however, as a thick gray cloud soon began to race toward us from the north. A flash of lightning prompted us to quickly seek out a place to change into non-sweaty clothes, and the subsequent downpour forced us into the Sloppy Tuna across the street. Blissfully un-crowded, I ordered that most quintessential of beach drinks—a Corona Lite with lime—and watched the teeming rain stir up the surf. Within 20 minutes, the downpour, which was much more Florida than Long Island in nature, ended, sunny skies returned, and I abandoned my beer in favor of that much more typical Montauk treat, the lobster roll. Red Hook’s variety (see review on page XX) are quickly becoming my favorite, and I enjoyed it on a newly-dry outdoor picnic table.

Walking around Montauk Highway, I reveled in my mini Hamptons vacation. There are few things as beautiful as a sunset over Fort Pond, and we took a much deserved, leisurely stroll from town to the train station, to be transported back to reality.

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