The Hamptons, the famed string of resort towns situated at the end of Long Island, isn’t famous for motorcycle riding.
For most residents and visitors the long soft, almost stereotypically beautiful beaches are the point. Another group goes for the social scene, a never ending cascade of glittering parties where the affluent try to outdo each other. In the New York City area, the real bikers head to the Hudson Valley. People may ride motorcycles to get to the Hamptons, but it’s not the purpose of the trip.
After my recent experiences, however, I would argue that this strip jutting out into the Atlantic Ocean is worthy of a motorcycle expedition.
The idea came from a friend and, if I am being honest, a sense of convenience. I live part of the year in New York City and I stash my Triumph Thruxton there. Eric just got a Triumph of his own and has a place in Bridgehampton. We both wanted to ride, but we were short on time, so he suggested we use his house as a base instead of making the trek to the Catskills.
My expectations weren’t high. Thinking about islands in Florida I expected long straight roads, with pleasant ocean scenery but not much variety. This idea was shattered as we hit the curves going from Watermill to Sag Harbor. The road was smooth and windy through a dense northern forest. Whitetail deer stood almost invisible as our engines roared by. We went fast, but not too fast as the road is patrolled by a series of aggressive local cops.
Sag Harbor is a charming little hamlet situated on the Long Island sound. It has the perfect affluent vacation aesthetic, with high end Manhattan restaurants situated alongside bikini stores, and even a few fishing boats still in the harbor for a bit of flavor. Vacation towns like this know how to capture a sense of updated Americana. It feels like you would imagine the nation in 1950s movies, pleasantville USA.
Less superficially affluent, but much more cool, was NYC Choppers. These Brooklyn transplants have set up shop right on the wharf in Sag. It was exactly what you want from a custom bike shop, one of a kind builds surrounded by a hoarder's den of parts, manuals, and bikini pin up calendars. I was surprised that they had a few custom Triumphs, some even with the high end components from my bike. My ego was stroked when they liked the mods I had done to my ride, and recommended that Eric do the same.
From here we boarder the ferry to Shelter Island. It’s a fun experience being out on the water with our bikes. If the Hamptons are flashy, then Shelter Island is the definition of quaint. Tasteful beach houses line clean streets. The roads were empty on this off season Monday, so it was the perfect opportunity to open the throttle up. Blasting alongside the water we really got to enjoy the warm fall sun and crisp dry air. Unfortunately the lack of traffic also meant a lot of the restaurants were closed so we went back to the ferry.
It was time for lunch, and this being the coastal North East that meant seafood. We stopped at a roadside joint just off of Route 27 and found a table outside. The first round was a dozen clams on the half shell, not something I normally go for but when in Rome... After that we had lobster rolls to complete the experience.
Montauk really is the end of the world out on Long Island. After lunch we continued onward, speeding past the sandy dunes of Amaghanset. The scenery really does change around this point, going from lush New England green grass to an almost Malibu landscape. Coastal pines take over and at narrow points along the road you can really feel the cool Atlantic breeze.
The scenery becomes even more stunning at the end of the line in Montauk. Overlooking cliffs you could see surfers like small dots out in the evenly spaced rolling waves. In the other direction was the Montauk lighthouse which sat perched on the end of Long Island.
We made our way back and it got me thinking, maybe I’d misjudged the Hamptons. In the past I had seen it as a stuffy unapproachable enclave but with Eric’s hospitality, curvy fast roads, and great Fall weather It seemed like it was worth a rethink. Going back towards New York on the grinding dirty Long Island Expressway I wished I could be on those bucolic lanes.
Fortunately I wouldn’t have to wait long for a second chance.
It was the end of October and Eric hit me up, “this Saturday is looking perfect”. We wanted to try something different, so we both decided to go to the North Fork, the tip of Long Island that faces the Sound and not the open ocean. For road guidance I turned to a favorite newsletter NYC Moto. He gives the best routes in the New York area. I subscribed and downloaded his google map for Long Island and the Hampotns.
After the Shelter Island ferry we decided to go straight for the end of the line at Orient Point. The North Fork is more bucolic than the Hamptons, full of good old fashion folks. We passed coast lines and farms until we got out to the point. Entering the park we took a short but incredibly scenic road to the beach. I would have never thought of going out here but the info from NYC Moto was incredibly helpful.
We started cruising back but along the way came across a beer garden with a live cover band. Eric is a former rock star and was diggin it. Because we were riding we had only one small beer, but the down home ambience and great five piece band was an amazing break from the pretentious Manhattanite vibes of the Hamptons.
This is why I love riding motorcycles, it brings you to places you would never go otherwise.