Counter Culture—A Connecticut Comfort Food Road Trip Last Updated 5/17

By Will Siss

The closest thing to time travel is a diner. Settling into a stool at the clean Formica counter or easing yourself into a plush booth, you’re transported to an era when people kept their eyes on each other, not a gadget. Perhaps we need them more than ever. Connecticut has plenty of diners and cafes built on integrity. Owners take pride in their prompt service, not to mention their thick-cut fries and blue-plate specials. Hop in. We’re taking a road trip! 

Three Generations

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.

Original Cheeseburgers & Milkshakes

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. 

Tree Rings & Onion Rings

Pulling into a spot at Sycamore Drive-In Restaurant in Bethel, we could simply flash the lights and receive one of the hallmarks of classic diner traditions: curb service from an attentive carhop. But we’ll leave the car behind and stride into this gem that takes its name from a 300-year-old tree just a few dozen yards from the humble-looking spot. Family-owned by the Austins for nearly 20 years, this cozy joint—that dates back to 1948—has all the trappings of a vintage diner: the checkerboard floor, Naugahyde stools and a long counter with a soda fountain that serves homemade root beer. The menu isn’t frozen in the past, however; it offers six different salads, including one with cranberries, walnuts, feta cheese and grilled chicken. Or, wrap your hands around their original steak burger for a taste of a true classic.

The Summer Cruise Nights on Saturdays bring folks from around the region as the block shuts down and the Mustangs, GTOs and Cadillacs take center stage. “There are so many people who tell me that they met here, that they had their first date here,” owner Patrick Austin said. “Coming here is kind of a tradition.” 

Race In & Take Your Time

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.

Coleslaw with a Twist

Simplicity is the key at Glenwood Drive-In in Hamden, where the service is fast and the hot dogs are long and perfectly charred. Known for their onion rings, hot relish and a unique twist on coleslaw (with just a little bit of pineapple), Glenwood has everything that a fast-food chain wishes it had: authenticity and high-quality food served quickly.

Upon entering the Glenwood, enjoy fried shrimp or savor a lobster roll at one of the 17 tables or one of the 12 swivel chairs. While the Glenwood is a drive-in by name only, you can certainly enjoy an order of clam strips or soft-shell crab at one of the outdoor tables. And when you’re done, there’s Kelly’s Cone Connection, an ice-cream parlor that shares the same building.

Like all great road trips, this one ends with a desire to seek out even more classic Connecticut diners exploding with character—and flavor. Find other great places to eat in Connecticut, here.