I’ve been wanting to do this trip for ages and this past weekend felt like the perfect time to go so I went.
I realize it’s technically not New York City…BUT Fire Island National Seashore counts as a NYC public park so therefore I can still call this NYC Trip #5.
Day 1
Today I left the house at about 4:15am. The plan was to drive to the Montauk Point Lighthouse first without using the ferry. I was a little worried about hitting the NYC/Long Island / Queens rush hour traffic so that’s why I left so early.

I get nervous when things are out of my control, which is why I didn’t use the ferry. And the fact I would’ve potentially gotten to the lighthouse later than I wanted.

Once I was in the car I didn’t get out again until Montauk…about 312 miles later. It took me nearly 7 hours to get there. I planned for 5.5 hours. Since I left at 4:15 am that only put me about 45 minutes behind schedule so not too bad. The original plan was to stop at the Camp Hero State Park and see the old radar tower, but I didn’t think I’d have time so I skipped it.
Montauk Village is vibrant! I didn’t think it would’ve been just by looking at a map. There were so many people there it seemed like a smaller version of Cape Cod. It seemed to be a more upscale destination as well. You probably shouldn’t come here if you can’t afford a corvette.

The lighthouse itself was about 10 miles past Montauk Village and much less busy so I suppose that means everyone just came for the beach, party boats, and resorts. That was fine for me! I get better BB8 pictures when there are less people around in my opinion.

The very southeastern tip of Long Island is where Montauk Point is. I went during a heat wave in the North East USA so that meant that it was super hot. Good thing I brought my sun hat!

The view was awesome! I was optimistic I’d have a clear sky and boom there it was. There were a lot of fishing boats in the ocean and you apparently sometimes could see a navy submarine on its way back to the submarine base in Connecticut. No such luck for me.

I walked around the base of the lighthouse on the beach. The beach is more of a rocky shore, which is good I guess since that means that erosion is not as prevalent. (The sandy bluffs did look in rather tough shape). This lighthouse is the oldest one in New York State. It was built in 1776 and commemorated by George Washington. I thought that was pretty neat.

The main draw of this place is being able to go up inside the tower so that’s what I did after going to the gift shop. I always have to visit the gift shop anywhere I go for a souvenir for the drawer at home. I learned in the gift shop that there is a passport for light house stamps (much like the National Park passport for national park stamps.) I will be trying to knock out some light houses here now haha.

The inside of the tower was surprisingly larger than I thought it would be. I had to climb a spiral staircase to the top and that was sort of hard work since it was so hot inside. Luckily I could leave my backpack at the bottom. The stairs were made of iron and were installed in 1836 when the tower was rebuilt. Originally they were made of wood. The employee at the top of the tower said that the tower was built first then the stairs after. I thought maybe the opposite based on how heavy each step seemed to be.

The view from the top was amazing! Totally worth it!

After the tower I walked back to the car and headed to my next destination: The Big Duck. It is located in Flanders, NY and was about a 1.5 hour drive away even though it was only about 45 miles away. That’s New York traffic for you! It went pretty slow for most of the journey. There were A LOT of nice cars. I’ve never seen so many BMW’s, Tesla’s, or Corvettes in my life. You need to be loaded to have a house here I think.

The Big Duck is actually smaller than I expected, but it was open for business! (This was one of those places where I couldn’t tell what the hours were so I just showed up and hoped for the best.) The man inside was very nice and told me about how architects from all over the world travel to this specific place to study “Duck Architecture”. Like to become an architect you need to visit this duck. I’m a bit skeptical of this claim so I will make sure to ask all my architecture friends if they too have studied the architecture of the duck.

The inside is a bit cramped, but I secured a few souvenirs and a gift. My old boss at the Boy Scout camp in Milton, Mass was the one to fist mention this place to me. Anytime I hear about an interesting location I add it to my Google Maps and I must say this spot was pretty cool.

The next place on the itinerary was Orient Point near the ferry terminal and it was about a 32 mi (1 hour) drive away. This part of Long Island was much less busy than Montauk so that was a welcome change.
I passed by Sag Harbor along the way. This seemed like a nice place to visit too although it was very crowded. There were a lot of big yatchs here as well as many fishing vessels. It would be a good place to people watch, but that sadly wasn’t in the plan so I kept going. Orient Point was not too much farther away and I ended up getting there quickly.

It turns out that it is private property! I ended up doing a u-turn and just heading to the hotel. It turns out that I was actually getting tired. By the time I pulled into the hotel parking lot I was on the verge of passing out. You see the night before I had really tried my best to finish the From The Vault #10 blog post and doing that meant I only got about 2 hours of sleep. 2 hours of sleep before a taxing 10.5 hour drive was really tough especially with the traffic.

Once checked in I went to sleep right away, barely woke up to post the FTV blog at 6pm, then went right back to sleep. At 11:45pm I woke up and went to a TGI Friday’s for dinner. It was the only restaurant that was close by that seemed good and it was open until 2am. The food was amazing since I had only had 2 gatorades, a liter of water, and 6 slices of bread for the whole day up until that point.

Overall today was a nice change from the sort of stressful week I’ve been having. Tomorrow I’m getting some more National Park stamps so that’s exciting! See you then!
Day 2
Today I got up at the reasonable time of 9:30am and set off on the adventure of the day at 10am. One great thing about a National Park site opening at 11am is that I get to sleep in!
Sagamore Hill lies south of Stamford, CN across the ocean. I was going to see the Sagamore Hill National Historic Site (Theodore Roosevelt home). It was only a 35 mile drive from the hotel and didn’t take too long to get to. The neighborhood it’s in is rather quiet, which is a surprise since it’s located so close to New York City. (Close is relative…I know you can’t take a subway there lol).

The plan was to just walk around the grounds since I didn’t have a house tour reservation. I was the first one to enter the park museum so I got to talk to the ranger about the tours and he said that there were 9 day-of tickets available. Great! The only problem was I didn’t really have time to wait until 12pm if I wanted to stay on the current time schedule of the Official Plan. Grrr. In the end I decided to go since I think it would disappointed me later to return home without the experience.
I had to wait about 45 minutes until the tour started so I spent that time in the museum doing the Junior Ranger Badge. You can be any age to do the badge (even though I know it’s technically for kids). I went through Theodore’s early life, then him becoming President when President William McKinley was shot, and then later after his presidency / death. At 11:45am I took the oath and became a Junior Ranger once again. Usually each park has their own oath.

The tour started outside of the home on the front steps. Mike was my tour guide and he apparently had 500 hours of volunteer service! He said that we couldn’t go up to the third floor since it was over 100F and he didn’t want anyone to faint. As soon as I walked into the house I was greeted by an immense amount of hunting trophies.


There were all sorts of animals…everywhere. A giant water buffalo was in the front hallway and his name was Fred. *later it was found out Fred was more of a Fredericka*. All the rooms had an animal hide carpet. The living room had a polar bear, the presidential study had a zebra and a mountain lion one. That was really cool to see! I’ve seen a tiger rug in the Pink Panther cartoon, but never one in real life.


Moving forward we entered what seemed to be the library and there were many foreign gifts on display. A samurai sword, a giant german fairy tale book, and a Japanese mini armor statue to name a few. There were two bison heads hanging on the wall.

I found it ironic that he hunted and claimed bison trophies even though he was credited with saving the bison in North America. (They would’ve been hunted to extinction if not for the preserve in North Dakota). There was an elephant foot trash can and a rhino foot ink well also in the room. A Rembrandt painting hung from the wall in the back corner. Probably the coolest thing of all was Roosevelt’s original sword and hat from his Rough Rider days.

Moving to the kitchen Mike said that this house was extremely luxurious not for the hunting trophies, but for the home amenities! There was running hot water and a flush toilet. Also a shower upstairs. Those were super new at the time and usually unheard of in other houses. The kitchen looked like most other NPS house tour kitchens. Roosevelt apparently LOVED fried chicken so there was a fried chicken and watermelon mock-up on the kitchen table. Apparently back in the day (1800’s) you had to dress up for dinner. Put on your best Sunday clothes and such. I can’t imagine doing that today for every dinner.


Moving upstairs we saw the bedrooms and nursery. They too had animal carpets in them. Upstairs was less exciting than downstairs in my humble opinion. This was the last part of the tour and I was actually getting used to the heat inside so I was a bit bummed that we couldn’t venture upstairs.

Outside it was mentioned that there was no railing here because Roosevelt liked to be as close as possible to the crowd when he gave speeches from it (the porch). Mike said that 200 years ago Roosevelt owned about 155 acres of land and that the row of trees in the distance weren’t there so if you stood on the porch you could see all the way to the ocean. There is a small forest there now and Mike said it’s private property so if the park service went with chainsaws there would be a lot of angry people.

After the tour I made my way to the sign to get a picture for Mom then I drove south to the Fire Island lighthouse. It is located just inside the boundary of the Fire Island National Seashore so I’d be able to get both the Fire Island Lighthouse stamp in my lighthouse passport and the NPS stamp in my National Park Passport! Cool!

Upon getting a parking spot I changed into my crocs since I didn’t like the idea of potentially getting sand in my sneakers. It was about a half mile walk out to the lighthouse on the boardwalk and took me about 10 minutes at a leisurely pace. It was about 85F, but with my sun hat I avoided getting any wicked sunburns.

Once I got to the end of the boardwalk, I first looked inside the lens museum building. It had the original lighthouse light inside and the staff member knew all sorts of stuff about its history. The light was made of one single everyday bulb and a bunch of curiously shaped glass panels. The light rotated clockwise to alert ships at sea of the sand bars and mainland. It was crazy to think a single bulb is what created all that light!

After taking a peak in the lens building I walked over to the main visitors center. It had the gift shop where I got both my National Park and lighthouse passport stamps. Also a patch for the souvenir drawer. There is a museum to look through as well next to the gift shop.

I headed upstairs first where the wall panels mostly talked about lifesaving. We can get into that a bit later. The lens building exists because in 1933 they swapped out the old lens for a new more powerful one, but the original was such a cool historical object that eventually they brought it back and put it on display. (There’s a bit more to it than that, but that’s the gist without boring you.)

After the visitors center it was suggested that I check out the boathouse next. It was located right behind the lighthouse tower on a small boardwalk. Inside I talked to another wonderful volunteer about lifesaving.


Much like Montauk, Fire Island boasted a mighty ship rescue crew at the lighthouse. If a ship crashed close to shore then the crew would fire a cannon (with a rope attached) to the vessel in distress. The thought was it would hook itself to the mast or rigging then the crew could secure it on deck. Then they would pull sailors across on a life ring style pulley system. Imagine a somewhat stable zip line over the ocean during a storm and that’s what you got.

There was also a sort of capsule thing that used to be used as well. Basically if your ship had hit a reef / sand bar the rope would be shot out to the boat, attached securely to something, and then a metal capsule thing would be attached to the rope somehow. You and about 7 others would get into the capsule (laying on top of one another) and pulled back to shore by the lighthouse crew. Eventually they stopped using that system because once you were in there was no way to get out from inside. If the rope broke while the capsule was over the ocean then it was game over for everyone inside.

There was also a small life boat that was ‘unsinkable’ that would go out if all else failed I guess. It was pretty big in size and rather impressive looking. After seeing everything in both the museum and the boathouse I headed back to my car.


At this point my foot was starting to hurt and so I thought it was time for a short rest at the hotel. (I possibly fractured a bone on the Mt. Washington hike. Yippee). It was also a good chance to write about today’s adventure.

Next I think I’ll try a local seafood place then go to bed. I’m getting up really early again to drive to Rhode Island tomorrow and I need my rest. (HA I ended up going to a Texas Roadhouse and having a nice 3/5 dinner because finding parking at the local seafood place was all but impossible with the beach-goers.)
Day 3
Today I got up around 4:25am and checked out of the hotel at 4:44am. The plan was to leave on the early side just in case there happened to be traffic going from New York to Connecticut. I ended not seeing any traffic as I crossed into CN at 6am and from there I headed to my first stop of the day: a rest stop just outside of New Haven, CN.

I did something similar in Colorado on the Nebraska trip in 2022. Basically if you leave a few hours early that gives you time to relax for a few hours somewhere else. I don’t need to be in Newport, Rhode Island until 10am, but since I was worried about traffic I left early and now I’m taking a break at a service plaza. Also a good chance to update the blog and get a donut from Dunkin’.
I hopped back in the car and drove the rest of the way to Newport, Rhode Island. Newport is rich in history, shops, and has lots of posh tennis enthusiasts. Why come to Newport to watch one of the most boring sports ever when you have the chance to tour the oldest synagog in the United States? (The joke here is that Mom comes to watch tennis in Newport and I think that is a waste of time.)

Touro Synagog National Historic Site is the oldest synagog in the United States. It is an affiliated National Park Site so that means while I can get the stamp and some souvenirs, it is privately owned so they do their own tours with no rangers on site. (At least that’s what I think it means.) The tour was first come first serve right at 10am so that is why I had to leave Long Island so early. I made it though!

The tour went over the history of the Jews coming to America and how they first built and then kept the synagog over a period of more than 200 years. They were fleeing persecution and somehow heard about Newport, RI being a religious tolerant city. Anyone could practice what ever religion they wanted. (Newport was also a bustling port city so that was another great reason to move here.)

The synagog itself has a traditional colonial look on the outside, but the architect put Sephardic Jewish religion features inside. The building also had unique windows. They were huge and often would be opened during prayer so that anyone that wanted to watch or listen could. The place where the rabbi stood was in the middle of the room at a huge podium. The men sat in chairs on the ground floor and the women sat on the top floor.

They believed in separating the genders and still practice that here to this day. I as well as the other guys on the tour had to wear Yamaka’s, which was kind of interesting since I’ve never worn one before. I don’t think it’s a good successor to the polar bear hat though.


After the tour I went to get lunch at a place near where I parked my car. I went to Benjamin’s! It is a local bar and pub in Newport. One of the specials was a lobster / mac & cheese grilled cheese. I don’t really eat much lobster so this was sort of a shot in the dark, but it turned out really good! After lunch I walked back to my car and drove back across the bridge to Jamestown, RI.

I had decided to go to the Beavertail Lighthouse, which is relatively close to the Touro Synagog the night before. It would be my 3rd ever lighthouse stamp in the lighthouse passport! Parking here was difficult, but I did in fact manage to find a spot. It seems like this is a good spot for picnicking and maybe the beach (although the shore seemed to rocky).

The lighthouse is smaller than Fire Island or Montauk, but the view was a lot better with the bright blue sky. I spent a lot of the time talking to the gift shop employee and one of the volunteers about the lighthouse, my trips, and whatever else came to mind. They were both very nice.

I wasn’t able to climb this lighthouse tower, but that was ok because they made up for it with a mini aquarium. I enjoyed the views for a bit then decided to head home. The Newport Cliff Walk would have to wait until another time.

The drive home went well, but I must’ve either hit Sumner Tunnel (closure) traffic or rush hour Cape Cod traffic on 93N so it ended up taking a bit longer than expected. About a normal Monday 1 hour to get from Milton, MA to home. (I wasn’t a huge fan of this, but it couldn’t be helped.)
After Trip Thoughts
“After trip thoughts” are supposed to be my personal thoughts at the end of a trip.

This trip went by fast. That was sort of a good thing since I’m not sure what I would’ve done in Long Island if I had stayed any longer. Try as I might, I wasn’t able to work Gateway National Recreation Area or Staten Island into this trip because Long Island is longer than I thought plus traffic would’ve been horrendous. I’m not sure what the best way to see those parts are.

Apparently there are 23 lighthouses on Long Island so I will probably have to return. The Marriott hotel in Medford, NY was great! I’d definitely stay there again. Anyways, that about wraps up this trip. See you next time!
Trip Stats

- Estimated trip milage: 765mi (I changed it to 885mi later after adding Beavertail)
- Actual trip milage: 907mi (taken from the car odometer)
- Lighthouses stamps: 3
- National Park stamps: 3
- Sharks seen: 0
- I wore crocs on the boardwalk at Fire Island
- Big ducks seen: 1
- Drove from Boston to Montauk without getting out of my car (314mi)
- Times I listened to Hardwell’s full set at Tomorrowland 2023: 4
- Didn’t see Brother Philip this trip sadly
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