Fairfield, Connecticut

Have you ever ridden a rocking and rolling subway just to catch a train from Grand Central… with an insane hangover… going off a guess on direction and destination? This is that story.

Earlier in the week, Ashley and I hit up the Lord Huron concert at Madison Square Garden with a childhood friend of mine. Admittedly, we’d never heard of them. The show was easy, fun, and a few songs even rang a bell.

During the concert, my friend invited us to the beach that weekend. We said yes.

Fast forward to Friday—Connecticut was happening the next day. (See: Frick post, Carlyle post… yeah, we made it.)

Up to this point, all I really knew about Connecticut was: Greenwich, ESPN, Mystic Pizza, and Hartford Insurance. I’d only ever been once—to Mystic—for this same friend’s wedding. Yes, that Mystic. Julia Roberts. Pizza. A classic if you know you know.

We hopped the 6 to Grand Central, and the only thing keeping the smashburger from the night before down was… writing. (Again—see Frick post, Carlyle post.)

This one I’m writing Sunday evening, as the flutter of the weekend settles. I’m comfortable. On my blue leather couch.

The whole commuter train thing—subway from all parts of New York, into Grand Central, out of the city—is surprisingly easy.

Here’s my take: it’s easier to just take the subway than to try and learn the subway.

We did it. Even boarded the New Haven line as the conductor yelled that we were holding the whole train up.

We didn’t have tickets. We didn’t have seats. We wandered through cars and eventually plopped onto a folded handicap seat. A lot of seats had space next to them, but people gave off “don’t sit here” energy. I learned on the ride back: you can just sit. Or ask. Or both.

From our perch, a couple with a massive suitcase boarded at the next stop and asked the people kitty-corner to us to scoot over. Ashley—angelic as ever—offered up our spots, so we swapped and ended up next to a middle-aged couple who looked equally relieved to not be stuck beside a giant suitcase. We were happy to have a window.

A few minutes in, the woman next to me pulled out a Playbill. You know the one. Yellow. Broadway.

So I asked, “How was the show?”

She and (quickly realized) her husband—sitting directly across from Ashley—had just seen the Michael Jackson musical. She said she thoroughly enjoyed it. Ashley and I still haven’t seen a Broadway show together. We almost saw Stranger Things but went to the Frick instead.

Turns out the couple was from New England and loved cats as much as we do. We ran through the whole first-time conversation circuit, even dipped a toe into politics.

The husband takes pens from restaurants and hotels. I gave him a DevHub pen.

They let us know there were two Fairfield stops—one and two—and we were the first.

Right before our stop, we shook hands, swapped numbers, and I’m pretty sure we’ll see them again.

On the platform, I looked right—and there was my childhood friend waiting. The air was perfect, like every New England coastal town we’ve ever explored—except now we weren’t just visiting. We had a real connection.

He drove us to the wine and cheese shop to stock up for the beach. We picked up this goat cheese in olive oil that will forever live in my top 5 cheeses list. If I had the name, I’d share it.

Fairfield and Southport are quintessential New England coastal towns. What does that even mean? No stucco. Wood signs with gold inlay. Businesses with names like “Harbor” or “Mariner.” The faint smell of salt, sea grass, and dampness.

The weather was perfect.

We toured his house, then piled into the car to meet his family at the beach. We talked NYC—restaurants, politics, the usual.

After an hour or so, we headed back and started prepping dinner. He grilled pork burgers, which sounds basic, but they were incredible. He called it a Santa Fe recipe. I’ll be stealing it. To accompany the burgers he insisted we try Sally’s Apizza so we quickly drove over and picked up two. I mean you want a review? Look it’s good like solid good and if I lived over there we’d get it again, but Pagliaccis is still my favorite - go Seattle and don’t come for me.

As night rolled in, we went to a local dive bar to play darts. I won.

Back at the house, he showed us the Wim Hof breathing method, shared new music, and we played Hues and Cues.

Ashley and I slept in the guest room.

Next morning: overnight oats and the farmers market. Then caught the 11:05 back to the city.

On the train, we asked someone to move over so we could sit together. No words needed—we both just sat there thinking how lucky we are… to zip across state lines and still come home to New York City.

The worst part?

I got a text from an franchise industry titan asking if we were in town to grab drinks.

Fuck.