Medford to Montauk: A 40-hour solo roadtrip

Montauk Point Lighthouse is pictured.

A fall holiday landing right at the end of midterms seems like a great day to unwind—to boot up a video game, movie, or just sleep in. For this Veterans Day, though, I had a plan.

An intense forty hours saw me visit the historic lighthouse at Montauk Point, travel to a grocery store to find a quite special seltzer water and squeeze in a few hours in Manhattan.

The influence of this trip was my personal “lighthouse tour.” Since coming to Tufts, I have been fascinated with the idea of a lighthouse. The iconography they hold as a stark, magnificent landmark of a typical New England coast. I have always loved expansive coasts, and a tower filled with rich history and an intricate construction enhances my enjoyment.

Wishing to leverage the convenient transportation that is so prevalent in New England, I was eager to use a Zipcar and then ride the Amtrak back. Being able to freely explore the area on the way to Montauk and then take a relaxing train ride, which has been heralded to people from the area as a “luxury experience.” Moreover, an extremely cheap Airbnb in Queens enabled me to spend the night here and then go to Manhattan the next day.

The day started early—around 5:30 am—about an hour before I planned to wake up. The feelings of zero fatigue, eager to experience, were a good sign to me. Each time this mindset emerges, I am assured that this will be an adventurous day—a memorable positive adjustment of my abilities.

I started off to The Fresh Market in Avon, Connecticut, where I could find Rambler Sparkling Water, a water brand from Texas of which I met the team behind it a month prior. I had found them in the spring of this year at a grocery store in my hometown, and I had gotten their attention on Instagram by aggressively tagging them in my posts. Later, I visited their office during my fall break from Tufts, where I got to meet all the employees at their small office in Austin. There, the founder told me about a grocery store—The Fresh Market in Avon—that was only one hour out of the way.

At the store, I found the water immediately and checked it out. I told the cashier about my story with this water, and we sat and tried it together—the perks of being so early to the store.

Then, the long haul drive began, which took five hours, from 9 a.m. to 1 p.m. The journey to Montauk did not feel long, at first. I prepared at least six hours of tech podcasts and a twenty-four-hour playlist, and they entertained me until I reach the start of Long Island.

Long Island, it turns out, was a lot longer than I anticipated in the cursory planning hours from the day before. At least two and a half hours of the trip was traversing those 118 miles to the tip of the island. I was very excited by the landmarks, though. Seeing signs for locations I had heard so much about, like the Hamptons, or seeing Manhattan across the East River was so exciting as I had never been so close to “cool stuff,” alone. I found myself feeling accomplished in the self-motivation that I had been able to generate impromptu.

Finally, I reached Montauk. The first thing I do is marvel at the lighthouse, after all, this is the first leg of the tour. Then, I take some drone footage, of which I have done on every vacation of the past year.

Afterwards, I went to the museum inside the lighthouse and looked at the artifacts, all showing the storied past of this lighthouse, dating back to 1792. I’d be remiss if I didn’t go up to the top as well.

At the top, I met Dan, the Montauk Historical Society member, who treasures showing those at the top of the lighthouse. We talked about the lights in the structure, and he explained to me why the Fresnel lens had to be changed from a higher to lower order. He explained how they had to tear down the staircase in the lighthouse to put in place the new lens. We talked about my drive from Boston this morning and the Boston Light, which, in Dan’s opinion, was worse than this one.

Leaving Montauk a little after sunset, I needed dinner, which, once again, required me to meet another person. I went to a marina searching for food, but only found a tackle salesman and his trailer, instead of a restaurant that was closed for the season. He was so curious as to why I was here, since I was his fourth visitor that day and the only one he didn’t know. He recommended a great local diner—The Point—where I had my first real meal of the day, the best Philly cheesesteak I’ve ever had. Sitting in this diner showed me that “small-town America” felt the same in Texas, my home, and here in New York.

At this point, I had to drive back up Long Island to my Airbnb, a drive that was just an extension of the drive to Montauk, something I was used to on this day. On the way back, I planned out my evening. I was only 45 minutes away from Manhattan when I got to my Airbnb via the subway, so I would be foolish not to be able to experience the typical tourist-y experience.

That evening was spent in Times Square, visiting the Plaza Hotel from Home Alone 2 and the Apple Fifth Avenue store. At the Plaza Hotel, I asked the security guard if this was the famous hotel, after which he guided me through all the set pieces from the movie in the lobby. The next day, I worked my way through various museums, parks, monuments, and stores of Manhattan, and went back to Tufts that evening.

Before this trip, I wasn’t aware of the positive impact one person can have on people, even given how insignificant both people involved in the interactions are to each other. I would not be able to discover this if I didn’t propel myself to plan this trip, and have the courage to execute it.

By this, I learned that people are usually open to a conversation, and positively interacting with someone through a conversation will brighten their day, and yours as well.

This piece was also published in the Tufts Daily.

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