Biking from Southampton to Montauk

Written By: Katie Laffey

The East End of Long Island is home to the oldest collection of historic windmills in the country. There are 11. The route from Southampton to Montauk passes by at least four. But most drivers will never notice them.

If, as so many motivational posters say, life is about the journey and not the destination, then life in the Hamptons is defined by aggression. Unless you have a bicycle.

My bike is 15 years old. It’s navy blue. It has black tires and 24 gears. Eight of them work. The pedals are lined with small metal divots on the top and bottom; and reflectors on each side. The cushion on the seat is extra padded, at an inch and a half thick. The chains are rusty, but they’re not in danger of falling apart.

Growing up in Southampton, home, the beach, Main Street and school were all within five miles of each other. A bike was the most practical way to achieve the errands a teenager needed to run. Flash-forward to summers home from college, and my siblings and I were searching for an adventure. We were too old to go to camp, but too young to explore the bar scene. We chose to bike to Montauk.

The trip along New York State Route 27 is 27 miles. The road is one lane wide for most of the drive. There are 10 stoplights. None of those are in Montauk. It takes about 45 minutes to drive it in the wintertime, and at least double that during the high season. We budgeted five hours for our journey.

Our trip began with an online map, accessed from our family’s desktop computer. Our printer was broken. Cell phones didn’t have GPS. We wrote down each turn-by-turn direction, orienting ourselves with a route that would keep us south of Montauk Highway for most of the ride. We committed the return Long Island Rail Road schedule to memory, and set off east along Hampton Road.

Leaving Southampton Village, we immediately headed for the first shortcut that every Southampton driver learns—the Cobbs. Flying Point Road to Cobb Road to Little Cobb Road allows you to avoid three-quarters of the congestion from the Water Mill traffic light. The Cobbs pass by a corn field. In early August, the stalks were coming in. They were taller than my bike. Ears of corn on the cob were tucked in between silky leaves. For the first time ever, I made a connection on the origin of the two street names.

Merging onto Montauk Highway a few minutes later gave a panorama view of Mecox Bay. A pack of swans congregated near the bridge. The Water Mill windmill came into view. It was built in 1800 and has stood in the hamlet’s green since 1860. It churned grain until 1887, when new construction along Mecox Bay blocked the winds. The day of our bike ride, there was a soft breeze. Like the cars, we were moving 10 miles an hour. But we weren’t focused on the color of the traffic light.

Heading East, we turned off of Montauk Highway and meandered around Water Mill and into Bridgehampton. If we hit the ocean, we turned around. If we hit the highway, we knew we had gone too far.

Beebe Windmill came into view at the corner of Hildreth Lane and Ocean Road. It looks similar to the once in Water Mill, but the National Registrar of Historic Places touts its technology. It utilized steam. Wind wasn’t necessary to power it. It was relocated throughout the East End five times, and its sails turned until the early 20th century.

A bike and a windmill both operate using a very simple gear system. It’s green technology, in use long before “green” referred to anything but a color. Shades of green are everywhere on the East End. Hydrangeas. Grass. Shallow ponds. The rough on golf courses. Hedges. Dune roses. Mallard ducks.

Green technology forces you to think about the environment, but more importantly, to also to enjoy it. Our first official stop of the biking journey was on the historic Sagg Bridge. Built in 1923, the bridge has a small walkway to throw fishing lines. Below, there is a launch site into Sagg Pond where people can kayak due south to the ocean. Here, there are no crashing waves. Only glassy water, surrounded by reeds. The bridge was recently the subject of small-town controversy that reached the federal level: It needed updates, but how can you do so without altering its rural character? The state came through with funding in July. It will maintain its charm.

Soon, stops on the bike ride became much more frequent. We had a picnic lunch in East Hampton. There’s a tree on the east side of Town Pond that is frequented by swans. Their white feathers contrast with the shallow, murky water. They don’t like it when bikers eat lunch close to the water’s edge. When open, their beaks are larger than a human fist.

Just behind Main Street is a duck pond. There are much friendlier fowl there. We were sorry that we hadn’t left any of our lunch to share.

East Hampton’s central business district could be a study in contrast. High-end fashion boutiques sit beside homes that pre-date the American Revolution. We pass the two easternmost windmills within a few minutes of each other. Hook Mill is at the entrance to East Hampton; and Pantigo Mill is at the exit. The two were built within two years of each other—1806 and 1804.

Our bike route mostly avoided Main Street. The ducks swimming a few hundred yards away from town didn’t know about the chaotic scene there. The drivers didn’t know about the peaceful one by us. Traffic persists, even though the road expands to two lanes. This is not because town planners had the foresight to know how popular East Hampton would become. The road is wider because, years ago, there needed to be space for the cattle grazing in Montauk’s open range to be herded through.

Just beyond the Main Street traffic light is a sign that says “Montauk” with an arrow directing drivers to keep going forward. No mile marker is listed.

The island quickly narrows. The air smells salty. Leafy green trees become hardier. These new trees thrive in sandy soil. The Napeague Stretch is long and flat. Here, cars pick up speed. The posted limit is 50 mph. Some go faster. The shoulder is wide enough for both of us. They don’t notice the small patches of blue ocean that peek through at just the right angle. Or the house with all of the buoys on its western facing wall. The sun beats down. It’s tempting to stop at Goldberg’s. But another iteration of the Famous bagel shop awaits just over a set of hills.

Soon, the road divides. Both sections are three miles long. Old Montauk Highway has rolling hills, no shoulder, and a few peeks at the ocean. New Montauk Highway is 1.5 miles up; and 1.5 miles down, with scenic overlooks. Over the years, we’ve biked both routes. I don’t have a favorite. Both allow us to coast downhill as we enter downtown Montauk. Both offer the best reward for completing the journey: A view of Montauk surrounded by ocean. The breakers roll toward the sand. The water is a very distinct shade of blue, separate from the sky. The occasional fishing boat bobs in the distance. We have a good five minutes to enjoy it, as we coast toward our final destination, the Welcome to Montauk sign. We’ve made it. We celebrate with a dip in the Atlantic, which is always more rough up close than it looked from far away. The salty water mixes with our salty sweat. We then go find lobster rolls.

Since that first trip, we’ve developed certain rules for the bike to Montauk. Always bring cash for lemonade stands. Always take a picture in front of the Montauk sign. Always be willing to jump in the ocean at The End. And always do the ride at least once a year. We’ve completed it 10 times.

There’s an old joke in Montauk that you’ll be sitting at a bar next to a hedge fund manager, a CEO and a surfer, and you can’t tell who’s who. Bike from Southampton to Montauk, and you’ll find that the spirit of the joke still holds true.