Recently, I was reading a letter from Steph Bohrer’s Close to Home snail mail club, which is all about travel, finding yourself, and change. It immediately made me think about a trip I took almost a year ago. There’s something funny about travel. We spend so much time dreaming about getting away, only to arrive somewhere completely unfamiliar and somehow find pieces of ourselves waiting there. And maybe that’s why this trip has stayed with me in a way I didn’t expect.
Last fall, I got to take one of those trips that had lived in my head for years. As a graduation gift for getting my Master’s degree, I got to choose a trip, and my choice was easy: Boston. I had romanticized Boston for years. The brownstones, the changing leaves, the history, the bookstores, the cobblestone streets. It felt like the perfect place to celebrate closing such a big chapter of my life.
I was also in a relationship that ended not long after the trip. Is there a correlation? Who knows. But I do know that something about that trip inspired me. It changed me. It opened my eyes to how much is out there and how badly I wanted to experience more of it.
Living in the Midwest can feel so… isolating. Which is a weird thing to say considering we are quite literally surrounded by states. But I mean it more in the sense that sometimes everything can start to feel the same. There’s no ocean. No mountains. No subway to hop on. Nada. Not many people are sitting at home dreaming about their once-in-a-lifetime vacation to Oklahoma. Sorry, Oklahoma.
Maybe that’s why my family has always traveled so much. We don’t want to become jaded by only knowing what we know. We want to explore. We want to see new things and meet different kinds of people. I think traveling reminds me that the world is really, really big, even when the place I live can sometimes feel really, really small.
But back to the trip.
Boston may have been the main event, but our trip actually started in New Haven, Connecticut, where I got to walk around Yale University. Visiting all of the Ivy League schools is one of those slightly random things that has lived on my bucket list for years, and Yale was officially the beginning of taking on that list. It also made all of my Gilmore Girls-loving dreams come true. I was Rory walking around campus (before she dropped out, obvi). The leaves were falling, the temperature was perfectly chilly, and the entire campus looked like someone had designed it specifically for an autumn Pinterest board. It was picturesque.
From there, we went to Newport, Rhode Island, where we toured The Breakers Mansion and spent the day wandering through a version of life that felt completely removed from our own. Giant rooms, ocean views, and the kind of old-money architecture that makes you briefly wonder if perhaps you were meant to inherit a seaside estate. Unfortunately, no long-lost Vanderbilt relative has appeared in my family tree. But a girl can dream.
The next day, we drove to Cambridge, where I got to walk around Harvard. Make that two Ivy Leagues crossed off the list. Harvard had me thisss close to walking into admissions and begging them to accept me, but alas, I refrained. Cambridge in general felt strangely familiar. It looked exactly how I had pictured it in my head, and maybe that’s why it felt like a tiny piece of myself was already there waiting for me.
Then there was Boston.
I rode the subway for the first time and, after that, many more times. And can we talk about the girls who ride the subway? People-watching quickly became one of my favorite activities. I watched girls get off after their 9-to-5s dressed in outfits that looked like they had been pulled directly from my Pinterest boards, heading somewhere with purpose while I sat there wondering about their lives. Where were they going? What tiny apartment did they call home? Did they have a favorite coffee shop around the corner? Were they meeting friends for drinks?
It made me yearn for a life that wasn’t mine.
And isn’t that one of the strangest parts of traveling? For a few days, you get to peek into other people’s ordinary lives, and suddenly their ordinary feels extraordinary simply because it isn’t yours.
If there is one place I can recommend every book girlie see at least once in her lifetime, it is the Boston Public Library. I could have spent the entire day wandering through it. The architecture, the books, the little corners that make you want to abandon every responsibility you have and become a mysterious woman who spends her afternoons reading in libraries. Somehow, it got even better when we stopped at the bar and tea lounge inside, where I had the best spiced pear mimosa of my life. I fall asleep dreaming about that place. I wish I were exaggerating.
We walked through the Boston Public Garden multiple times, and somehow it never felt repetitive. One of my most vivid memories from the entire trip is actually something completely insignificant. A stranger’s scruffy little dog kept dropping his ball about five feet away from himself and watching it roll toward my feet, patiently waiting for me to throw it. Naturally, I obliged. I probably spent twenty minutes playing this game with a dog whose name I don’t even know.
I miss that scruffy guy.
Beacon Hill was everything I wanted it to be and more. I wandered past brick buildings, cobblestone streets, window boxes, and front doors that looked like they belonged in a Nancy Meyers movie. I was in heaven. Then we went to the North End, aka Boston’s Little Italy, where I ate some of the best cannolis I’ve ever had. When people say it feels like a little Italy, they mean it. For a moment, it felt like we had been transported somewhere else entirely.
We also spent a day in Salem, where my woo-woo heart was completely full. We sight-saw, ate entirely too much good food, walked until our feet hurt, and filled our days with all of the things you’re supposed to remember about a trip.
But strangely, those aren’t the things I think about first.
When I think about Boston, I think about my dad.
I think about being 24, fresh out of grad school, and standing in that weird space between who I had been and whoever I was becoming next. For most of my life, there had always been another step waiting for me. Finish high school. Go to college. Graduate. Go to grad school. Finish the internship. Complete the next assignment. Get the degree. There was always somewhere I was supposed to be going.
Then suddenly, I had done it.
I had graduated, and for the first time in a long time, the next version of my life wasn’t written neatly on a syllabus.
Maybe that’s why this trip feels different when I look back on it now. I was traveling through all of these new places at the same time that I was entering a new version of my own life. I didn’t have some dramatic movie moment where I stood in the middle of Boston and suddenly understood exactly who I was and what I wanted. I’m not sure finding yourself actually happens that way.
Maybe it happens in smaller moments.
Figuring out a subway map. Walking through a place you’ve dreamed about seeing. Ordering a drink in a beautiful library. Crossing something off your bucket list. Watching strangers on the train and wondering what it would be like to live a completely different life. Laughing with your dad after you’ve both walked way too many miles that day.
Growing up is strange because you don’t always realize something is becoming a memory while you’re living it. At the time, my dad and I were simply on vacation. We were figuring out where to eat next, which train to take, and how much more sightseeing our feet could realistically handle. I wasn’t thinking about how someday I would look back and realize how special it was to have that uninterrupted time together.
We’re already planning to go back next year. What can I say? I think we left a little piece of ourselves in Boston.
I know I’ll remember Yale and Harvard. I’ll remember Newport and Salem. I’ll remember the Boston Public Library, the cobblestone streets of Beacon Hill, the cannolis in the North End, the subway girls whose lives I invented from across the train, the scruffy dog in the Public Garden, and that spiced pear mimosa I will probably spend the rest of my life trying to find again.
But more than anything, I’ll remember that my dad was there beside me for all of it.
And I couldn’t help but wonder: maybe we have the idea of travel a little backward.
We think we leave home to find something new. A new city, a new experience, maybe even a new version of ourselves. But sometimes, you travel hundreds of miles away and discover that the things you were searching for weren’t necessarily waiting at your destination. Maybe the new place simply gave you enough distance to see what was already there.
The world is big. My little corner of it is small. And there are still so many places I want to go, people I want to meet, trains I want to ride, libraries I want to get lost in, and versions of myself I haven’t met yet.
But maybe being close to home has never really been about where you are.
Maybe sometimes, home is simply the person walking beside you.
Ashley ♡
Little moments I captured
