Last weekend a friend and I went out on an adventure to circumnavigate Long Island Sound entirely by public transport. We planned it out ahead of time to ensure we wouldn’t get stuck anywhere, but also left room for impromptu changes and called a few audibles along the way.
A big thanks to Charles for planning this out and partnering with me on this! Check out his thread on Mastodon if you want to get his perspective of the trip (he live posted along the way).
NJ Transit from Denville to Newark Broad Street
Our point of departure was Denville Station in New Jersey. It was relatively close to us, parking is plentiful and cheap ($4 per day), and has regular service to NYC to get us started. We hopped on a NJ Transit train heading to Newark Broad Street.
NJ Transit from Newark Broad Street Station to Hoboken Terminal
Out first change was at Newark Broad Street Station. We could have gone further and taken a more direct route, but we had plans of hopping a ferry in Hoboken as opposed to staying on NJ Transit and using the tunnels into NYC.
NY Waterways Ferry from Hoboken to New York City Midtown
I was already having fun, but arriving at Hoboken Terminal started to step up the excitement. It was a bustling terminal with a few modes of transport all coming together. Inside the official station was quite impressive and nostalgic. We purchased our next tickets (for the ferry!) and then we walked around a bit to take in the views of the waterfront.
Soon, our ferry (NY Waterway‘s Fred V. Monroe) arrived and we hopped on board to set out for NYC.
New York City
We had just enough time after arriving in NYC to take the subway to our hotel, check in, then take another subway downtown for a quick bite and a movie at Film Forum.
Tonight’s feature was Coffy, a blaxploitation film from 1973. The theater itself was comfy, the screen was amazingly crisp, and the audience added the icing on the cake. It made the evening to sit there and let loose, laughing at the jokes as well as the ridiculousness along with everyone else. At one point there was a very racially charged scene (also as ridiculous as the other action sequences) but the audience went silent. It was a rather uncomfortable scene, but I appreciated that we all seemed to be sharing the same discomfort.
On our way back to the hotel we paid Grand Central a quick visit. The next day we would be in the new Grand Central Madison wing, and not passing through the original main hall.
LIRR from Grand Central Madison to Ronkonkoma
Early morning in NYC is pleasant. The crowds have dispersed, yet the coffee and food is still wonderful. This was made even more enjoyable by exploring the brand new Grand Central Madison. The newness, cleanliness, and expansiveness were quite impressive, though I noticed it did struggle with the hostile modern public space design trend regarding lack of seating.
As we set off on the Long Island Rail Road, we started talking about the historical reasons for various public transport designs in the northeastern United States. Specifically we discussed SEPTA, about which Charles took great pleasure in drawing some maps to provide additional visual context 🙂
Rumor has it the SEPTA system may be one of the next adventures.
LIRR Transfer at Ronkonkoma to Greenport
We had a very brief stop at Ronkokoma Station – literally a 10 foot walk across the platform to hop the next train.
This section of the trip was exactly what I was hoping for. Part of my reasoning for being interested in this particular route was that I have never been visited Long Island (I don’t count Brooklyn, and I’ve been told by Brooklynites that is NOT on Long Island regardless of what cartographers want to tell you). I love challenging my preconceived notions about things, and I couldn’t imagine Long Island being anything more than just a sprawling extension of New York. The passing landscape slow faded from a cityscape of apartment buildings to smaller towns and ultimately to some local farmland, orchards, and a surprisingly high number of vineyards.
Exploring Greenport
Greenport was great. Immediately after leaving the train, there’s a small station repurposed into the East End Seaport Museum. I wanted to support the museum so I picked up a DVD documentary about the history and restoration of Long Beach Bar “Bug” Light lighthouse, and a a U.S. Lighthouse Passport.
Lunch at Green Hill
We left the station area and started to explore downtown Greenport itself. It’s a very cute town that I greatly enjoyed and will definitely be making a return visit.
For lunch, we decided on Green Hill Kitchen and Cue. Relaxed, taking in the surroundings, and enjoying conversation, we mostly lost track of time and started wondering if our food would be arriving shortly. I’m not exactly sure how much time had passed but it was definitely longer than one would expect, especially considering most of the patrons had cleared out from the morning brunch.
After the quick distraction of someone walking into the restaurant with a full-sized chicken costume and firefighter helmet (sorry, I didn’t take a photo of that one), our waitress returned with the bill and quietly said “but no rush”. I think she could tell we were enjoying ourselves, however she had also forgotten to give our order to the kitchen. We casually mentioned we hadn’t received our food yet, which generated immediate fear and embarrassment. We said we were in no rush, and our food came out right away with much haste. I can easily say it was worth the wait! Our waitress was still obviously embarrassed and told us our meal was at no charge. However, since we had appreciated the rest of the service, had been truly enjoying ourselves, and genuinely savored the food, we made sure to leave her a tip in hopes of restoring some of her confidence and not casting a pall on her day.
After lunch we wandered around town some more including a few side streets because they simply looked interesting. Then we found the next connection we needed: The Suffolk County bus stop.
Suffolk County Bus to Orient Point
The bus was a bit late and had no live tracking feature so we were a little concerned at first if this would be our first hiccup of the weekend. Waiting had treated us well so far so I pulled out my e-reader, started reading and patiently waited.
Sure enough, the bus came and we were on our (short) way to Orient Point.
Orient Point Ferry to New London
Coming off the heels of Greenport, I wasn’t sure if the next leg of the journey could compete. Little did I know something would be waiting for me, Adirondack chairs.
We bought our ferry tickets to cross the sound to Connecticut and sat on the beach in very comfortable Adirondack-style chairs, soaking up the sea breeze. We watched our ferry, the Susan Anne, come in to port and unload. The Susan Anne was also a car ferry, but to our surprise this also included an RV and a full-sized tractor trailer. We watched the cars as they boarded and were amazed at how it seemed to swallow the truck whole; nom nom nom. We boarded and just as we were about to leave port we found more Adirondack chairs on one of the decks. It was the perfect place to enjoy the ferry ride and do some more reading.
New London
Coming in to New London was fun. Not only is the town called New London and we were on a boat, but the river we took leading up to port was called the Thames and we saw a few old fashioned sailing ships. It felt like a classic end to a great day. From the river we saw Fort Trumble and the Kalmar Nyckel,
Shore Line East from New London to New Haven
The next morning we walked back down to the waterfront and got our tickets for the start of our return journey aboard Shore Line East towards New Haven.
Metro-North from New Haven to Bridgeport
We transferred at New Haven and took the opportunity to explore the station a bit. It was another example of a wonderfully maintained classic large rail station. I appreciated the underground walking tunnel connecting the train platforms with the main station. It was architecturally interesting, but also executed quite well. The floor was tile while the walls and ceiling were metal but there was hardly any echo. I looked closer and noticed that the metal used had millions of very small holes seemingly improving the acoustics.
Bridgeport Ferry to Port Jefferson
At this point of the trip we did get a little wet. The weather wasn’t cooperating but we opted to stick with our plan to take another ferry. After all, we couldn’t break our streak of a ferry a day! The ferry port was a 5 minute walk from the train station and had a small food counter to grab a bite while you wait. Perfectly timed.
The rain came and went a few times, pausing for long enough for us to get out on the deck and look around. The wind was intense. Despite having been drizzled and rained on, I dried out in no more than 45 seconds. After a few close calls of almost losing my glasses I went back inside to relax and do some more reading. No Adirondack chairs on this ferry, though.
Suffolk County Transit from Port Jefferson to Ronkonkoma
We arrived in Port Jefferson and had a less than savory experience. First, we were welcomed to port by a gigantic and divisive Trump banner. Regardless of your political views, purposefully alienating 50% of your clientele is probably not the wisest business decision, and apparently the local townspeople aren’t pleased with the personal agenda tactics either.
We wandered around town trying to find the bus stop we needed. Google had it clearly marked but there wasn’t a single sign in sight. We even found the local Chamber of Commerce and stopped in, but the person working was far more concerned about getting her mask back on to be of much help. After trying to explain a few times that I didn’t need a bus schedule, I just needed to know where the bus stop was (and having the worker continue to insist must be I needed a schedule), I left no more enlightened than I walked in. We gave it our best guess and waited where we thought the bus would be.
While we sat waiting on a bench, some rather superficial and completely drunk people walked by, one of which almost ran in to me and 1/2 fell over on top of me before continuing on their way. We saw a bus arrive, start to slow, and then take off like a bat out of hell. We realized it was probably our bus so I yelled, Charles ran, and between the two of us we flagged down the bus and hopped on. It was the right bus after all, and the driver was apparently in as much of a hurry as we were to get the hell outta Dodge.
LIRR to from Ronkonkoma to Penn Station
Once back in Ronkokoma, we picked up our next tickets and boarded the good old friendly environment of a train car. Time to sit back, relax, and travel like civilized people again.
NJ Transit from Penn Station to Denville
Our stop in Penn Station was going to be tight. We divided and conquered, Charles wen to buy tickets for us while I picked us up some dinner. We met back up, hoofed it to our platform, and boarded NJ Transit once more for the last leg of our journey.
Here’s the thing. If you know me, you may be impressed by my actual reaction to what happened next. I consider it personal growth. As we sat in the mostly empty train car waiting to depart, an entire team of college-aged soccer players from the UK boarded. They were still in uniform and were obviously coming direct from a match. The B.O. smell was only matched by the apparent digestive struggle these guys were having with American food.
It was overwhelming, and I practiced my grounding techniques to make it through the smells, noise, and chaos. But here’s the thing, as I sat there hoping every stop would be their stop, I started thinking back on the 2.5 days of travel that was wrapping up and easily acknowledged was an enjoyable success it was. Did I wish my last segment was a bit more peaceful? Sure. But they were having fun and I had been having fun and ultimately, tolerance is key. I told myself that it wasn’t enjoyable in the moment, but it would absolutely add some color to my story.
The only thing remaining to figure out now is … where to next?
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