Sports, Fitness & Wellness

My Biking Adventure to Montauk

What is it about Labor Day that makes us reflect on the summer season? It’s not like I anticipate Thanksgiving Day by thinking about how nice fall was. I don’t spend Memorial Day reminiscing about the past spring. It’s just summer—sandwiched between two decisive holidays, the latter signifying slight sadness toward the fleeting warm days. And, like any East Ender, I’m asking the proverbial “Where did the season go?”
The solution to my cooler weather blues is to be outside and soak up as much sun as possible. And I still have one more item to check off of my summer bucket list—complete my yearly bike ride from Southampton to Montauk.
The idea for the inaugural ride was born out of necessity, as the saying goes. The “need” was to get out of the house—I was craving an adventure. So my brother and I hatched a plan. We would bike the route to Montauk, using as many back roads as possible, and take the Long Island Rail Road back to Southampton.
Luckily, someone had uploaded directions onto, a fantastic resource for counting miles. It would weave in and out of the potato fields and rows of corn, past mansions and down roads so flat and expansive, I would have thought we were miles away from civilization. (And, in today’s sense, we were. iPhones didn’t exist—we navigated via a map and a sense to keep the water to our right.)
It was a fantastic trip. All 33.43 miles.
The beauty of biking is that it encourages meandering and discovering natural hidden gems, and it fits the diversity of an East End lifestyle. I had never been to ‘downtown’ Wainscott (it’s small); had never actually seen the one-room schoolhouse in Sagaponack. We traversed quaint, narrow stone bridges, spotted tiny duck ponds and small estuaries. And on the Napeague Stretch, we encountered a road sign—pictured here—whose meaning bafflesd us. Caution, Giants Carrying Trees?
Whether for recreation, transportation or as a cure for boredom, biking is accessible to  most everyone. Bikers are invited to go at their own pace and log as many or as few miles as desired.
Thinking about hitting the road? Respect for your surroundings is key. The New York State Department of Transportation has a number of tips to help bicyclists and motorists safely share the highway. Obey traffic signs and signals, ride single file and always wear a helmet. Never ride against traffic, and always make eye contact with drivers when trying to cross a road.
And, if you choose to ride at night, New York law requires a white headlight and a red rear reflector or taillight.
I heeded to the latter warnings later that same summer. We enjoyed biking to Montauk so much that we decided to challenge ourselves again. But this time, we would bike to Montauk Point. To see the sunrise. It was a great idea when we thought of it late one night, and an even better one when we woke up and left the house at 1 a.m. We took Montauk Highway all the way. This ride was more about racing against time than the previous one.
Was it awesome? Yes. Will I ever do it again? No—the Napeague Stretch is pitch black at 4:30 a.m. And the choice between biking through the woods on New Montauk Highway or up and down the winding hills of Old Montauk is a sort of double-edged sword. But, the sunrise was beautiful, as the lighthouse’s red stripe was illuminated by the blazing red sun. Perhaps even more fulfilling was stopping at Mr. John’s Pancake House to refuel after reaching the Point. We then fell asleep on the beach and woke up to the late-morning light, just in time to catch a westbound train.
It was glorious, and I’m constantly reminding myself that beautiful fall days make for great rides—it eases the transition of seasons. I’ll be out in Montauk sometime soon for sure.

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