A Trip to Montauk | 2023

Montauk, New York

MONTAUK, NY - It was my first visit to Montauk and after this trip it certainly would not be my last. Being from Massachusetts, I would usually be driving down to Rhode Island or Cape Cod as a summertime beach destination. While nearly everyone from Massachusetts flocks to the Cape and Islands, Rhode Island, Maine and New Hampshire, for summer vacations, I wanted to venture off to explore someplace else. I would soon find out why Montauk or “The End” is a popular spot. It was mid-June, just before the summer rush. A few days to find out what Montauk was about.

About Montauk

Montauk is a hamlet of the Town of East Hampton, NY, with a population of 4,318, according the 2020 census. Despite the low resident population numbers, Montauk transforms into a summer destination hotspot. The median price of a home in Montauk is $3.3 million, well beyond my budget, but it sure is a great place to visit.

How We Got There

We took the ferry from New London, Connecticut via the Cross Sound Ferry. The fee of $165 covered the cost of a round-trip ticket for a car and two passengers. The trip by boat was an hour and twenty minutes, it didn’t seem that long and it was a nice easy ride. There was plenty of space to sit, eat, read or go on your electronic devices. I grabbed a bacon egg and cheese sandwich from the Cross Sound Deli aboard the boat. Before I knew it we were ready to get into our cars and depart onto Orient Point, NY.

From Orient Point it would be a two hour ride to our destination in Montauk. The weather was rather overcast and cloudy this morning. The ride along Route 25 through this part of Long Island was a nice drive. The area was very rural, farmland and vineyards were plentiful along the way. No highways, just single lane roads. It was a long ride but it was a relaxing ride.

From Orient Point it would be a two hour ride to our destination in Montauk. The weather was overcast and cloudy that morning. The ride along Route 48 through the northern portion of Long Island was a nice drive. The area was very rural, farmland and vineyards were plentiful along the way. No highways, just single lane roads. It was a long, but relaxing ride. This portion of Long Island was a whole other destination to explore for another day.

Things got a little more congested in traffic as we rounded back east on Route 27 through the Hamptons, but it was still bearable. Taking in the sights of some places we’ve never been, making notes on places to go in the future and taking note of some of the places that I just can't afford. Once we made it through some slow traffic it was back to easy driving east along the Montauk Highway. Running a bit early for our hotel check-in time, the skies were still overcast, so we headed direct to the end of Long Island, to the Montauk Point Lighthouse. Our total trip time including drive and ferry time was about four and a half hours.

The Montauk Point Lighthouse is the nation’s fourth oldest lighthouse in continuous operation and the first of New York State. The lighthouse was authorized by President George Washington and the Second Congress in 1792 and was constructed on June 7, 1976 and completed on November 5, 1796. Since 2012 this location has been designated as a National Historic Landmark. The exterior of the lighthouse was undergoing some work while we were there but it did not take anything away from the experience. It was a few bucks to park and then $15 per person to enter the lighthouse museum and go up into the lighthouse. A great historical location for anyone interested in lighthouses and local history of Montauk and Long Island.

After leaving the lighthouse, the clouds began to clear and the sun was starting to break through bringing out the blue skies. We checked into at the Montauk Blue Hotel, situated right on the Atlantic Ocean. An ocean front room with a sliding glass door right to a deck area where we could sit out and only a few steps to the beach. Montauk Blue is in a great location to downtown Montauk, only a few minutes walking distance to plentiful shops, restaurants and bars.

After enjoying the beach for a while it was dinner time. There were plenty of great places to choose from to find something eat. A few of the restaurants weren’t open on certain days that we were there, because the summer season was not yet in full effect. We choose to check out The Point Bar & Grill, a small local restaurant along the Montauk Highway. It was a laid back atmosphere with rustic wooden floors and wooden booths, just the kind of place that was a fit for me. The Point Bar & Grill describes itself as “Old School Drinking Since 2000.” A place that was fairly busy and the bar was filled with vacationers and locals. They had a wide variety of options to choose from on the menu and everything looked great. We started off with some house mixed drinks and had an appetizer of potato skins. For an entree I had the local cod fish n’ chips. Overall great experience, with great food, drinks and atmosphere.

There were plenty of great places to choose from to eat. A few of the restaurants weren’t open on certain days we were there or had certain hours, because the summer season was not yet in full effect. We choose to check out The Point Bar & Grill, a small local restaurant along the Montauk Highway. It was a laid back atmosphere with rustic wooden floors and wooden booths, just the kind of place that was a fit for me. The Point Bar & Grill describes itself as “Old School Drinking Since 2000.” A place that was fairly busy and the bar was filled with vacationers and some locals. They had a wide menu and everything looked great. Started off with some house mixed drinks and had an appetizer of potato skins. The old school, real potato skins that are hard to find in any good restaurant where I come from. For an entree I had the local cod fish n’ chips. Overall great experience, with food, drinks, and atmosphere.

Across the street was the infamous Memory Motel which according to local lore is where the Rolling Stones once hung out while staying at Andy Warhol’s Montauk home. Legend has it that the Stones were looking for a bar pool tables and piano, and the Memory Motel was that spot. Inspiration for the 1976 song “Memory Motel” from the Rolling Stones Black and Blue album. After hours the iconic Memory Motel dive bar becomes one of the many popular nighttime hotspots of Montauk after Memorial Day.

We walked around the downtown Montauk area, visited a few shops. Most stores closed early during this time of the year, but we would visit some of the shops in the days following. Even though we visited out of season, I was amazed at how quiet and peaceful it was. There were so many great places to eat in the area, we hadn’t got to them all, but it just adds to our list of things to do on our next visit. Montauk is a quaint little place to visit. The infrastructure, buildings are reminiscent of what it was in the 60s. It almost looks like a movie set. Many of the buildings appeared original stock of the later of the mid-century, some long standing businesses and some that appeared new, but carrying business in the old structures. There is a common with a gazebo at the center of it all. In speaking with some local people at the businesses, they say once school is out and the summer season arrives Montauk becomes a very busy place.

The next day we got up early in search of where would we have coffee and breakfast. Our sights were on either Anthony’s Pancake House or John’s Pancake House, each located near each other, but on opposite sides of the Montauk Highway. Both had good looking menus. This time the decision was for Anthony’s. Established in 1952, which maintained its mid-century diner vibe. The atmosphere was great and our server was nice. Being a pancake house, of course I opted for the pancakes, bacon and the “famous home fries.” After breakfast we enjoyed a couple more cups of coffee before we would walk around to some of the shops and then hit the beach.

Dinner that night was at was the the local historic Shagwong Tavern. According to their web page, the Shagwong has been in place for almost 100 years, originally opening in 1936. The bar area appears all original woodwork and with old photos lining the walls and a place that holds the authentic charm of its originality and longevity. The Shagwong's New England Clam Chowder was some of the best that I have had in a long time, it had a nice hint of bacon flavor, blending well with the chunky potatoes and generous portions of clams. The atmosphere was cool and you could tell that this old bar is a hopping place for night life during the summer season. Looking around at many of these local spots, they keep late night/early morning hours. I thought that many of the area bars would be a blast if I had visited here in my early twenties. But now I am middle aged and the late night bar scene isn’t for me anymore. Sitting on a bench sipping on a coffee watching cars go by or spending a day on the beach is now my speed.

We didn’t venture far from our hotel, we remained fixtures at the beach for the next day. The surf was larger than many of the Rhode Island beaches that I usually frequent. Miles of beautiful beach and oceanside landscapes to take in.

One of our days the weather was cloudy with some off and on rain. We took a short drive to the north side to Montauk Harbor, a nice place to park and walk around. Given the weather and time of the year, it was pretty sparse and many places were closed and little activity. This was just fine for me, as I prefer no crowds. We walked along West Lake Drive, visited a couple open shops, had nice frozen drink and sat along the harbor at Gosman’s Dock and watched boats come and go. Gosman’s has a whole complex of restaurant and bar facilities in this area. A great place to sit out along the waterfront.

For breakfast on our final morning we visited the Montauk Bake Shoppe, an old school style bakery located in downtown area. Amazing baked goods, cookies, pastries, donuts, breakfast sandwiches and more. When you aren't eating pancakes at either Anthony's or John's Pancake Houses, this is the place to go. Their custom blend of coffee was great. It is self-service coffee, so you can make it just how you like it. I opted for a bacon egg and cheese on one of their bagels. We found a seat at a picnic table just outside and watched the world go by as we ate. This will be one of our go-to places on future visits. We did make stop back there before we departed Montauk and picked up some cookies to take home. After our final day at the beach it was time to head home, but before we did, we grabbed sandwiches from M&R Deli for something to eat for the boat ride home. Traffic was dense as we traveled west along the Montauk Highway, adding on another 30 minutes to our estimated two hour ride. We cut it close and made it to the ferry at Orient Point just in time.

Had a great time in Montauk. I can’t wait to go back. While I didn't venture too far off for photography, what I have posted here is just some of the sights around Montauk that I saw while I was there.