Counter Culture—A Connecticut Comfort Food Road Trip

It’d be hard to find a more authentic diner than Zip’s in Dayville. Designed by the Jerry O’Mahony Diner Company of New Jersey and built in 1954, the classic dining car features all the elements you desire: stainless steel all around, bright red counter seats and booths made for snuggling while you eat. And “EAT” you must, as Zip’s iconic sign says out front, rising like a monolith to the heavens.

Named for a retired Connecticut state trooper who ran the original Zip’s on Route 6, the diner is on its third generation of family ownership. As its website invites, one must “indulge in affordable meals” once in a while, and this is the place to do it. With choices that include omelets and hotcakes, served all day, Yankee pot roast and baked meat loaf, diners at this diner walk away stuffed, especially when they indulge in Zip’s well-loved coconut cream pie.

If there’s one thing that Shady Glen Dairy Stores in Manchester are known for, it’s the cheese on their burgers. Four slices cover each “Bernice Original” burger, and the melt-over gets crispy on the griddle. But there’s so much more to this clean, efficiently run, homey restaurant that was designated in 2012 as an American Classic by the James Beard Foundation. 

“Some folks stop by for two or three meals a day,” a manager said, and it’s easy to see why. Everything from the lighting to the coleslaw says “comfort” here. Even the fanciful mural of elves frolicking in a garden while enjoying king-sized milkshakes puts one in a sense of whimsy and relaxation.

Shady Glen, which was built when it really was in a shady glen, also satisfies with its homemade ice cream, and a butterscotch sundae makes for an amazing bit of decadence. 

The “Black Duck” in Westport’s Black Duck Cafe has historically been associated with speed, so it’s ironic that this small restaurant is all about slowing down. It is diner-sized, but the Black Duck invites you to enjoy a great meal without the rush. And with items on the menu such as steak au poivre, you will want to take your time to savor every bite.

In the 1920s, the original Black Duck served as a “rum runner” in Westport. The 50-foot, liquor-toting vessel outgunned the U.S. Coast Guard during Prohibition. In 1978, Peter Atkin opened a restaurant with the same name on the Saugatuck River, in a converted ice-and-refrigeration barge built in the 1840s. Today, a long bar that runs nearly the length of the vessel awaits thirsty landlubbers, and 13 tables in the dining room greet hungry families. The real draw is the food, particularly the seafood and burgers. From whole-belly clams to fried oysters, soft-shell crabs to a lobster Reuben, there’s tremendous variety. The Black Duck’s burgers have a strong reputation, including Pete’s Stuffed Brie Burger and the Big Top Burger, which features bacon, fried onions and barbecue sauce.