I dared to dairy in my quest for the best grilled cheese the 068 could offer. Gone were vivid images of the famed sandwich of my Generation X youth — Kraft American cheese (orange!) freshly peeled from plastic wrappers, placed strategically between Wonder Bread (middle-of-the-loaf pieces preferred), toasted to crispy perfection with an assist from Land-O-Lakes salted butter. And a healthy side of Campbell’s tomato soup for the dipping, All My Children forthe watching.
Instead, what I found was not your grandmother’s grilled cheese, not even your mother’s. My flavorful discoveries were surprisingly elevated: one hearty, another fancy, yet another with a nod to yesteryear – all with a unique twist on this cherished lunch classic. My top picks include sandwiches suited for the barbecue-lover, the gourmet enthusiast, and the traditionalist.
Cody Sperry found inspiration in Austin when touring the city’s famed barbecue joints. When he returned back up north, Sperry put to practice what Texas had taught him. Enter Hoodoo Brown BBQ 967 Ethan Allen Hwy, a Ridgefield favorite he opened a decade ago, offering arguably the best amped-up “outlaw barbecue” around, which brings me to their Brisket Grilled Cheese. At $18, you get a two-handed sandwich stacked with wood-smoked brisket, cooked “low and slow for 16 hours,” atop mouth-watering cheddar; it’s a meal of the “Go Big or Go Home” ilk. The selection of southern-leaning sides was equally as impressive — from cornbread to pit beans to sweet and spicy Brussels sprouts, among others. I opted for the down-home potato salad with a kick to it.
“The Brisket Grilled Cheese has been a staple sandwich on our menu since we opened in 2015. Chopped smoked brisket, cheddar cheese, and buttery toasted sourdough bread. Can it get any better than that?” says Sperry.
The Terrain Garden Cafe nestled within the beautiful plant and home decor store, Terrain, offered a softer spin on the grilled cheese. At its 561 Post Road East locale, the Cafe is a delight for both the eyes and the tastebuds, adorned with rustic decor, festive lighting, and exposed beams, a cozy space where wicker and plants abound. I sat among the lucky who had reserved spots, a mixture of coffee-and-tea-sipping remote workers, friends, and colleagues.
Humbly listed on their brunch menu as Grilled Cheese, there was nothing simple about it. It was perfection on the plate: gruyere layered with sweet fig jam, crispy apple slices, and basil on sourdough bread drizzled with vincotto, a sweet condiment made by the slow reduction of wine grapes. Every bite was a sweet and savory sensation, a marriage of the very best kind. The spa day of grilled cheeses, it’s a steal at $15, offered with plain or truffle fries or dressed greens. I opted for the salad, though had to quell the YOLO quip, “Buy the shoes, eat the fries.” Terrain’s fancy take on the grilled cheese was on toasted sourdough, the pandemic’s darling. “There’s no better way to honor the classic reputation of a grilled cheese than by sticking to its simple perfections. Add a subtle piece of basil for a unique twist, and enhance the complexity and depth with vincotto on the exterior of the sandwich, which adds a bite of vinegar and a smooth, rich molasses sweetness that creates layers of flavor you can’t get enough of,” says Executive Chef, Jessica Bengston.
Finally, in the grilled cheese-as-comfort-food category, the winner was Wilton’s landmark diner Orem’s, 167 Danbury Rd., owned by Demetris Papanikolaou and established in 1921. At the crowded counter, I ordered a throwback from everyone’s childhood, and it delivered. The no-frills, gooey grilled cheese came in hot at $5.79. Fans can customize theirs with a choice of cheeses (American, Swiss, mozzarella, or cheddar), breads, and sides. I went for Swiss and tomato on rye, though bacon beckoned. A classic side of thick-cut fries, coleslaw, and a pickle completed the culinary picture.
“The grilled cheese is the quintessential American sandwich that we’re introduced to very young. As our palate matures, we move on to fillings like tuna, bacon, tomato, hamburger patties, corned beef, and pastrami. I often eat a traditional grilled cheese as it’s quick, easy, and accessible: the crunch of the buttered and grilled bread, coupled with the saltiness and melty texture of the cheese…it’s just hard to beat,” said Papanikolaou.
Whether a smokey sandwich seeker, a modern-day grilled cheese gastronome, or old-school nostalgic, find your fave and cheese it up! Timelessness guaranteed.
