The trick to showing someone around Yale isn’t to be comprehensive. It’s to be persuasive. You’re not just pointing at buildings—you’re trying to translate the strange charm of this place into something that sticks, something your sibling might remember the next time they walk past a Gothic arch or order a late-night snack they didn’t know was tradition. This isn’t a campus tour. It’s a soft argument: that this place matters, and that you matter in it.
So here’s where I take mine.
You start with the classics. The Yale University Art Gallery is always first—it’s free, it’s serious without being overwhelming, and it lets you pretend you’re more cultured than you were in high school. From there, head to the Beinecke Rare Book & Manuscript Library, where the books are encased in a marble-lit tower and the air always feels reverent. Then walk them into Sterling Memorial Library—not just for the sheer scale of the nave, but for the Alma Mater mural overhead, a quiet invocation of the university’s imagined guardianship over knowledge. It feels like a chapel to learning. (The bathrooms, for what it’s worth, feel considerably less historic.)
Next, I show them the old classrooms. Not out of academic pride, but because there’s something grounding about sitting in a Linsly-Chittenden lecture hall with its worn wood and creaky floors. It’s Yale at its most self-aware—its most beautiful, maybe, in the way old things often are. If there’s time, I show them the view from the top of the Klein Biology Tower. It’s brutalist, yes, but the vista stretches all the way to the Sound. It reminds you this is a city, not just a campus.
Then we eat. If I’m feeling generous (and if they’ve brought snacks from home), we’ll do the full New Haven pizza pilgrimage: Sally’s, Pepe’s, Modern, and BAR. Everyone has opinions. Let them form their own. For something slightly less touristy, I like Tre Scalini and Zeneli in Wooster Square—two Italian restaurants with warmth, character, and pasta that makes you slow down. If we’re staying close to campus, Miso on Orange always works for a casual sushi lunch. And in East Rock, there’s Caffe Bravo, which is low-lit and comfortable and feels like somewhere you’d go with someone you trust.
At some point, I make us move. There’s the run up East Rock, of course—either for the view or the validation. You can walk up St. Ronan Street behind the Divinity School for a quieter, slower route. Or rent bikes and follow the Farmington Canal Trail all the way to Sleeping Giant. It’s long, flat, and strangely meditative. New Haven peels back as you go—less brick, more sky.
Back on campus, there are rituals to uphold. Show them your buttery—even if it’s closed, even if they’re confused. Go to Good Nature Market at night, when everyone’s a little tired and a little wired. Buy them a bag of chips and a drink and explain that it’s not about what you get—it’s that you get it at “Ghav.” It’s a rite of passage with fluorescent lights.
Let them sit in a hammock in your college courtyard, even if it’s cold out. Tell them this is what counts as leisure here. If they’re lucky, maybe there’s a Toad’s event they can get into. Let them dance badly and feel like they’re part of something.
Because my family is Catholic, I always take them to St. Mary’s Church. It’s the birthplace of the Knights of Columbus, but more than that, it’s where our faith feels tangible—held in brick and stained glass, in silence and space. It’s quiet. Still. When we step inside, it feels like something familiar has followed us here. A reminder that Yale isn’t just a place for ideas—it’s a place that holds memory. Institutions live here, and they outlast us.
That’s the real thing you’re showing them, in the end. That this place is older than us, stranger than us, but that we’ve made a life here anyway.
