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Why Montauk:

The Hamptons are a collection of beach towns on the eastern end of Long Island, 2-3 hours east of New York City. They are world famous for being a fancy getaway for New Yorkers. Having never been to The Hamptons, I set my sights on Montauk, the easternmost town. 

I picked Montauk because several of my New Yorker friends and acquaintances seem to go there for weekends and because my college friend Ali currently lives there. 

Staying in The Hamptons is exceedingly expensive. There are very few hotels and the cheapest Airbnb listing I found was for over $400. Luckily I was able to find a hotel room for the bargain price of $180. 

The Hamptons are easily accessible via public transportation. There is a bus called the Hamptons Jitney or the Long Island Railroad.

May 14, 2022: The End of Long Island

The Hampton Jitney left from a stop 10 minutes from my apartment. Despite the name jitney, the bus was very plush. Sleek leather seats, air conditioning and a free bottle of water. There were a mix of passengers from hot moms to college students to older couples, but everyone appeared to be very wealthy- you just know. 

The ride to Montauk went through nearly all of the towns making up The Hamptons. East Hampton appeared to be the most upscale. Montauk was another hour from East Hampton along a two-lane road that apparently is clogged with traffic during busy summer weekends. 

I arrived in Montauk approximately 3 hours after leaving New York City. I stepped out of the bus into the world-famous Montauk only to see…a giant traffic circle ringed with space 1-story buildings. “This is it?!” I asked myself.

I walked two minutes over to the 668 Gig Shack, where my friend Ali was wrapping up her lunch shift. Since I had not yet eaten, I ordered two locally caught fish tacos with a mango salsa. It turns out that the fish was caught by Ali´s ex-boyfriend, a commercial fisherman. The tacos were surprisingly delicious but at $24 for two tacos, it was a sticker shock even by my New York standards. 

My surprisingly good $24 fish tacos

I also ordered a beer and starting chatting with the staff including Ali´s husband, Eoghan – yes they both work at Gig Shack. They met while working at the bar. After downing my beer, I helped Ali roll napkins for the dinner shift and then waited for her to cash out. The money is really good in the service industry here. It is very possible to make more than $1,000 a day in tips if you work lunch and dinner. The catch is that the work is seasonal. The “season” officially is Memorial Day to Labor Day. During the off-season, the town is very quiet. However, Eoghan explained that with the rise of remote work, the busy period is extending from early May to October. 

With my friend Ali

Once Ali had cashed out, we got in her car for a tour of the area. While the center of Montauk is small, the town is quite extensive. Our first stop was Camp Hero, an abandoned World War II air force base turned state park. The mysterious radio tower was the subject of many local legends and inspired the popular TV show Stranger Things (the original title of the show was Montauk – the location was changed to Indiana after the crew struggled to find filming sights in town). 

The infamous Camp Hero radio tower

Walking distance from Camp Hero is the Montauk Point Lighthouse. Located at the very eastern tip of Long Island, the lighthouse is the oldest in New York and the 4th oldest in the entire United States. Unfortunately, the lighthouse was closed for construction. 

The Montauk lighthouse

We then headed back to town. We first stopped at Ali´s residence. While staying in Montauk for most of the year is reasonably affordable, the prices in the summer are outrageously expensive. Therefore, most leases are only for the off-season and workers must find other accommodations. Many people stay in housing provided by their employer. Ali and her husband rented a room in a house owned by a local family. I find the housing shortage ironic given that most houses are humongous with plenty of extra bedrooms and completely unoccupied during most weeks even in the summer. 

Next, we drove to the owner of Gig Shack´s home to pick up one of Ali´s coworkers. Then we drove to an apartment complex to pick up another friend who is an artist. 

With the crew assembled, we drove to a classic seafood restaurant in the marina. There, we saw Ali´s ex-boyfriend´s fishing boat. In the restaurant, we tried to hook up one of the friends with the waiter. We were not successful. 

Our first stop on the bar crawl

Then we drove to a bar to see a local band play. We missed the band´s set but met a bunch of locals and played pool. 

Next, we went to a cocktail bar where the manager was a high school friend of the artist. 

Finally, we ended the night back at Gig Shack. Ali´s husband Eoghan was bartending. The bar was packed with service industry people and by this point I seemed to know half the bar! It was a great vibe with a live band playing. At midnight, Ali gave me a ride back to my hotel where I passed out.

The most expensive hotel room I have ever purchased

The next morning, I got a bagel and walked over to the train station. Having nothing else to see, I was ready to head home. 

Final Thoughts:

Given Montauk´s world-famous reputation, I honestly expected more. It’s a small quaint town, but there really is not much to see beyond the lighthouse. The beaches are nice in the summer, but that´s about it. The woods seem nice too, but apparently there are too many ticks to safely hike in the summer. However, my main turn-off is the prices. Montauk is one of the most expensive places I have ever visited. My hotel, a very average motel, was $180/night. The next cheapest option was over $400. As a budget traveler, the bar has to be very high to justify $400/night. For that price, it is probably cheaper to fly to Costa Rica or Cartagena, Colombia and rent a house there for the weekend. No joke!

For this reason, I would not recommend Montauk for the average tourist. There are equally nice beach towns all over the northeast including the Jersey Shore, Delaware, Rhode Island, and the Massachusetts Bay Islands that are way cheaper and have more hotel stock.

That said, I do understand the appeal of having a house here or visiting someone with a house. Chill Montauk represents the yin to the yang of hectic Manhattan. Montauk and The Hamptons are a place to recharge while still being able to stay in the NYC social scene. The unique geography and public transit connectivity of The Hamptons ensures that it is exclusively a NYC getaway. Additionally, the party scene is strong. I was there during the “off-season” and the bars were still decently busy.  Now that I have so many friends in Montauk, I will certainly be back as it seems to be the type of place that gets better with every subsequent visit.

It would also be remiss to not mention the service industry workers. In just the short amount of time I spent at Gig Shack and the bars around Montauk, a funny scene emerged with the staff. It seems like everyone is friends with everyone. They all know each other, pick up shifts at each others´ bars and then spend their money drinking discounted drinks at each others´ bars and leaving generous tips. They all seem to date each other and have tons of juicy gossip. Working here – especially during the summer season – seems like a lot of fun.

While The Hamptons seem to be very anti-development, I do think that the town can be improved with more buildings and apartments for service industry workers without compromising its character. To me, Montauk could become a modern Newport, Rhode island.


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