As someone who doesn’t drive, I tend to stick close to Metro-North or subway lines when traveling. This often means that places just two or three hours away by train (but a much shorter distance by car) end up on my Google Maps bucket list—destinations I dream about but never actually visit. But recently, my wonderful friend (and equally wonderful driver) Sruthi and I decided to break that pattern with a road trip to New Milford, CT—partly for its Gilmore Girls-adjacent scenery, and partly just for the heck of exploring another state.
Longtime readers know that Connecticut was something of a stomping ground for me in my early 20s, but this was a new area, so I was excited.
I watched the first season of Gilmore Girls during the iconic autumnal, pumpkin spice season in which everyone wants to cozy up and imagine that they live in a small and charming New England town. To my happy surprise, New Milford actually encapsulated the vibes that I was looking for.
Sruthi and I made the trek over in admittedly snowy conditions, and for a while all we saw was the highway and dead trees, until suddenly, the landscape opened up, and there it was: the postcard-perfect town center of New Milford.
One of the main Gilmore Girls connections was the gazebo in the center, so Sruthi and I were quick to snap some photos with it.
We parked the car and took a stroll down the main strip, passing a library, an arts center, a mix of boutiques, and a handful of restaurants. Eventually, we wandered into the River & Rail Café for brunch, which seemed to be a local favorite.
Whether I'm at home or traveling around, I love going to small coffee shops and trying their newest flavors, people watching through the windows and just chitchatting! It's essentially all my favorite things wrapped in one.
We then wandered around the town for a few hours, walking into different stores and bookshops. They had a massive vintage store called The Hunt that sold everything from kitchenware to prints to old hats from the 40s.
While walking around the store, we saw that they had a few brown paper 'jewelry mystery bags' for only 10 dollars each, with some vague descriptions of what might be inside, so Sruthi and I both grabbed one.
I’m going to take a little detour here to talk about friendships in your mid-20s—something I’ve been navigating mostly through Bumble. Sruthi and I met on Bumble, as did many of my closest friends in NYC, and what I love about meeting people this way is that there’s an inherent mutual understanding: you’re both actively looking to be a good friend to someone.
We went into it with the mindset of “This person I’m meeting right now could become someone I couldn’t imagine my life without.” That kind of possibility exists in all friendships, of course, but what makes Bumble special is the intentionality of it—you’re actively seeking out connections rather than just stumbling into them. In a way, things like day trips or coffee dates feel like courting your friends—spending time together, making memories, really getting to know each other.
More than ever, we have the ability to choose our friends, and I’m so grateful for the circle I’ve built, thanks to apps and social media.
Perhaps my favorite part of the entire day was when we just happened across the Village Center for the Arts. This place was incredible—not just because of the sheer amount of crafting materials, classes, and community activities they offered, but also because the staff was unbelievably friendly.
As they explained the studio fees for open crafting sessions, Sruthi and I found ourselves seriously considering whether it would be completely ridiculous to drive all the way from NYC just for an hour-long pottery class.
In the center of the room, there was a pole covered in different colored tapes, each strip written on by different visitors with the phrase “Push this button if…”.
Naturally, since we were having so much fun, we had to add our own push-style prompts (my genius tape idea was 'Push this button if you like pushing buttons') but it was just the kind of place that makes you want to leave a little piece of yourself behind.
We wrapped up our day of exploring with some ice cream (there was no way a little cold weather was going to stop us from getting a sweet treat). As we ate, we opened our mystery bags, and I was pretty happy with what I got. It was all costume jewelry, retro-inspired if not actually vintage, and for just $10, I loved how everything followed a cohesive color scheme and vibe.
I don’t own a ton of jewelry since I mostly just wear earrings and my engagement ring, but I’ve been wanting to accessorize more to elevate my outfits.
I had such a wonderful time here and I'd absolutely want to come back when it's a bit warmer out to enjoy a nice sunny day on the grass, so I'm sure this won't be the last time Sruthi and I visit! As always, thank you so much for reading :)
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