Something I’ve always liked about Heirloom, the restaurant at The Study at Yale hotel, is the seating fit for many purposes: the low and social lounge areas, the long party table tucked behind the host station, the elegant bar seating for lone wolves or budding packs, the array of two- and four-tops varied further by an ovular mini conference-style table confidently plunked in the middle. Something else I’ve liked is that it feels upscale but not isolating, with people-watching possibilities both as watcher and watched, at least if you’re sitting next to the floor-to-ceiling windows raised a few feet over the sidewalk.
That’s where I was, in one of the lounge-style setups, when I ordered a riff on something timely as we enter May: Heirloom’s non-alcoholic Margarita ($11). Milder and more effervescent than a standard margarita, it carried less of the lime tartness, none of the tequila bite and an unexpected but not unwelcome helping of fresh orange sweetness (courtesy of the orange juice subbed in for the usual triple sec). Vanilla and pear undertones, which I later learned are endemic to the non-alcoholic agave spirit used in place of the tequila, also made this a drink I probably wouldn’t describe as a margarita stand-in. Instead I’d give it its own name, with the confidence that it’s really tasty and can stand on its own.

Still in a mood to teetotal, I tried another non-alcoholic offering: The Privateer ($11). Fruity to the max with funky passionfruit puree, sweet pineapple juice and acidic squeezed lime, it was made even better, along part of the rim, by an artful sweep, like an emo kid’s bangs, of the most balanced tajín I think I’ve ever had—salty and spicy without being at all overwhelming. Delicious.
In between, I started my dinner with the Spring Mediterranean Salad ($14), hold the feta. I hoped the white balsamic, red onions, green olives and orange supremes would combine for enough salty funky brightness so as not to miss the cheese. And when I speared everything onto the same forkful, that hope was mostly satisfied, though, thanks to the physics of tossed salads, I had to dig to find most of the olives and orange. The watercress was bountiful and beautiful, the edges of every leaf singed purple-black as if by fire, with a flavor potently earthy enough to survive the mild sweet dressing.

My entree was the Cauliflower Bistecca ($26, pictured at top), a draw for plant-based diners and perhaps more economical ones too. (It was roughly half the price of the $49 Grilled Ribeye Steak, which advertised a fairly similar profile as far as the side components: whipped instead of smashed potatoes; broccolini instead of broccoli.) On their own, the romesco sauce and the “herbaceous marinade” each felt uneven. Together, however, they struck a really nice balance, almost like a cheesy marinara. The cauliflower had a pretty good sear, imparting the edges with a smoky crisp, though I would venture that the “steak” was sliced too thick, preventing the interior from cooking to that tender melt-in-your-mouth space cauliflower is capable of. The creamy, oily stewed butter beans below were unreservedly delicious, as were the “smashed” potatoes, which read more like sliced medallions. Oddly, I only found one piece of the advertised broccoli—broccolini, actually—in the entire dish, which was too bad, although, in every other way, the portioning felt large.
When it opened along with The Study in late 2008, Heirloom was the new, trendy, upscale kid on the block, getting headlines for the big-city pedigrees of its early head chefs and justifying its name with a farm-to-table focus invoking heirloom produce. It’s now one of New Haven’s more venerable fine-dining establishments, truer in age to its name by the day and rather quietly settled-into. In fact, it doesn’t feel to me like much has changed since I first came here well over a decade ago, and it still doesn’t feel like much if anything needs to.
Written and photographed by Dan Mims.