Some of the best travel moments can’t be planned. They just happen — and then they become the story you tell for years.

Earlier this year, my sister, my daughter, and I took the train into New York City for one reason: to see Hadestown on Broadway. Broadway theater has always been my favorite part of this city — there’s nothing quite like watching the lights go down and knowing you’re about to experience something unforgettable live. And Hadestown delivered every bit of that magic. But ask any of us what else we remember about that weekend, and we’ll all light up talking about a scrappy little afternoon spent digging through racks of vintage clothes before we ever took our seats.

We’d booked a vintage shopping experience through my travel membership almost as an afterthought — something to fill the hours before curtain call. It turned out to be one of the most memorable parts of the whole trip.

If you’ve never gone vintage shopping in New York, you’re missing something the guidebooks won’t tell you about. Forget the chain stores you could walk into in any city in America. We ducked into narrow, sunlit shops packed floor to ceiling with clothes that had lived — jewelry with someone else’s history in it, coats that felt like time capsules, racks where every single hanger held a tiny mystery. You never knew what you’d find next, and that’s exactly the point.

What made it unforgettable wasn’t just the clothes — it was who I was standing next to. My daughter, discovering that the styles she loves today are just yesterday’s fashion come back around. My sister and me, running our hands over fabrics that instantly pulled us back to our own younger years. Three generations, one afternoon, and an entire city block we never would have wandered into on our own. We laughed. We modeled ridiculous finds for each other. We lost all track of time. That’s the kind of afternoon you can’t schedule — you can only stumble into it, or seek it out on purpose.

Because here’s the truth about travel: years from now, you remember the conversation as much as the show itself. The moment someone pulled a perfect vintage jacket off the rack and gasped. The uninterrupted hours with people you love, in a place that felt entirely your own.

I found this experience through my travel membership, at a discounted rate I couldn’t have gotten booking it myself — which is exactly why I keep using it. Not just for train tickets and hotels, but for the small, unexpected experiences that end up meaning the most.

So yes, Broadway will always be my favorite reason to go to New York. Hadestown was the heart of this trip, and nothing will change that. But the vintage shopping tour was the perfect add-on — the kind of extra that turns a great weekend into a truly memorable one.

Here’s what I’d tell anyone planning a trip to New York — or anywhere, really: don’t let the famous landmarks be the whole story. Broadway and Times Square are wonderful, and you should absolutely make time for them. But leave room for the smaller, quieter adventures too. A vintage shopping afternoon. A neighborhood food crawl. A cooking class tucked away on a side street. Step off the path everyone else is walking, even just for an afternoon, and I promise — that’s where the extra memories are waiting.

Because when we look back on our New York weekend, we’ll always say it was the trip where we saw Hadestown — and spent a golden afternoon treasure hunting through vintage New York, three generations deep in someone else’s history, right before the curtain rose.