Who Knew: Taking the Eight Sandwich Challenge


‘Who Knew?’ is sponsored by Walter Stewart’s Market.

Once upon a time, men dressed like Cary Grant, and sandwiches were what people ate for lunch.

From kindergarten classrooms to corporate boardrooms, one could observe people at midday consuming an ingeniously portable combination of ‘bread’ and ‘things.’ There was an order to life, and while I’m not suggesting that correlation is causation, it’s worth noting that, back when we all ate sandwiches, nobody wore Celtics jerseys on airplanes or flossed their teeth on the subway. 

Perhaps it’s a profusion of choice–granted, much of it positive and health-minded—that’s gotten us away from such norms. Kindergarteners, if Instagram is to be believed, now dine on elaborate bento boxes of hand-shelled edamame, hummus, and gluten-free, organic pretzels. Office folks can now Uber Eats an uninspired hexagonal tub from Sweetgreen, undertip the guy in the lobby, and sprint back to volley emails into oblivion. 

It’s also the sandwich’s fault, or at least the modern fast-casual incarnation of the sandwich’s fault, that our ardor for a handheld square of lunchtime bliss has cooled. Have you ever been to a Panera? I shudder. Sandwiches have become bready and enormous, and they’ve played it fast and loose with quality like so many black olives (whyy) flung around an I-95 Subway. 

But a sandwich, as we head decisively into back-to-school season, can be your tiny moment of joy in an otherwise unpredictable day. Bread-things-bread is, after all, a mathematical equation not unlike the Golden Ratio, unassailable in its perfection. And here in New Canaan, dozens of sandwiches do it just right, all awaiting your discovery, to be placed in the lunchtime pantheon that restores a hint of classical order to our chaotic, technologically hopped-up lives. 

Over the past two weeks, assisted by a very eager Sandwich Research Associate™, to whom I am married, I conceived of and executed the Eight Sandwich Challenge. We hit our favorite spots, and probably grievously overlooked others, so this is a very imperfect starting point.

That said, let’s go!

A BLT from Walter Stewart’s

Crunchy, bacony, not enough lettuce to pretend it’s a salad-y goodness.

The Stewart’s deli counter buzzes with lunchers at midday. While their intuitive selection at the salad bar and *fantastic* hot soups account for some of the traffic, the rotating array of special sandwiches (announced daily on their Instagram) is the siren song that most often draws Sandwich Research Associate out on a lunch run, and possibly why his reception there rivals that of Norm on Cheers. One recent Monday, a Healthy BLT was on the docket. During peak tomato season, a tomato-forward sandwich is a must. This one featured turkey bacon, though I opted for that of the pig (sorry, health!), heirloom tomato, field greens, sharp cheddar, and chipotle aioli. It was a flavor-packed take on a century-old classic, with bacon crisped to a perfect shatter. The tomato was juicy, and its flavor shone despite other, more dominant notes. It was a summer afternoon packed into a few perfectly constructed bites; nary a leftover crumb made it to our anxiously waiting dogs. It’s also worth noting that, in an inflation-weary world, this was the lone sandwich that came in under ten dollars. 

Pro tip: These chips are just below the WS deli counter, and they’re an absolute revelation. Try them with a glass of cold, crisp wine at cocktail hour


Gourmet Grilled Cheeses from Plum Plum’s

Some college kids return from semesters abroad rolling the r in “ciao, ragazzi” or with a pack-a-day Gauloises habit. I returned from my semester in Europe with one belief:

Plum Plums grilled cheeses: flawless. No notes.

that the panini press is the pinnacle of human achievement. Plum Plums, our town’s sparkling jewel of a gourmet cheese and gift shop, is where we can make all our meltiest dreams come true. Their press-grilled cheeses here are lovingly constructed from the shop’s variety of cheeses, mustards, jams, meats, and even chocolate. An elegant, Willy Wonkafied spirit pervades the phenomenally imaginative sandwich menu.

Two favorites we frequently order are the Twice as Nice (Prairie Breeze and Cabot clothbound cheddars, apricot-orange jam) with its complex interplay of bright sweetness and umami and the Dutch Master, a simple but superlative combination of Prima Donna gouda and caramelized onion chutney. Asked for comments, Sandwich Research Associate noted that the sandwiches feel light, ungreasy, and savory, with a great multigrain bread that stands up mightily to the cheese. I agree. Too much time is given to just-okay grilled cheese sandwiches in our precious lives, and the first bite of a Plum Plums sandwich makes you want to block Kraft Singles’ phone number forever. 

The Godfather at Silvermine Market

Few sandwiches in the world can top an Italian sub (I know we’re supposed to call them ‘wedges’ in the Northeast, but please give this Californian a pass) for flavor-per-linear inch, and the Silvermine Market makes theirs with love and care. This charming country mart across the street from the Silvermine Arts Center is always worth the

The Godfather from Silvermine Market. And to think I almost made it through this blurb without making an “offer you can’t refuse” joke.

drive, and on a sunny afternoon, we made our way there to place our order. Billed as ham, pepperoni, soppressata, provolone cheese, lettuce, tomatoes, and onion with Italian vinaigrette on an, if we must, ‘wedge,’’ the result is more than the sum of those parts, with a perfect chew to the bread and the crisp, cool snap of veggies balancing out the spicy meats. Sharing one for lunch means you only have to worry half as much about the nitrates and sodium that an Italian sub implies, and you can focus instead on sheer deliciousness. It’s a delightful break from routine, and with road construction being what it’s been lately, it took us through several lovely neighborhoods to get there. Some might have been in Wilton or maybe Pennsylvania; I’m not sure. There have been quite a few crews on the road this year.

The Korean Style from Maddie’s 

Fried chicken sandwiches have enjoyed due glory lately, partly from the Popeye’s vs. Chick-fil-A standoff in 2019* and a northward proliferation of the Nashville hot chicken phenomenon (notable area standouts include Haven and Howling). It’s great to know that several of our hometown spots are in on the fried chicken sandwich game because, on some days, nothing else will do. 

Crunchy slaw on a sandwich is always a good idea.

I’m never going to be 100% sure why Connecticut Sandwich Company rebranded and reopened as Maddie’s. Though the online reviews have been equally sparkling, the menu became markedly less varied and more burger-focused, ruling it out for us most days. But there are often business model reasons for change that my selfish, nostalgic brain fails to grasp. And anyway, my opinion matters little as I’m probably not the target demographic; an in-person trip revealed a friendly crew and mobs of cute New Canaan kids enjoying a burgery moment. I definitely liked the Korean chicken sandwich with slaw, pickles, and K-sauce (a funky, jammy chili sauce, from what I could tell);  it checked the salty, umami, and tangy boxes that a sandwich must sometimes check. The sweet potato fries with comeback sauce were flawless, which is worth noting, as fries don’t always make the trip home so well. Once I recover from all of these sandwich lunches, I’ll have to try Maddie’s burger to understand if the change is, indeed, additive to our community. 

* Popeye’s won


The Burtis at The New Canaan Butcher Shop

Praise has been heaped on this Burtis Street newcomer since they opened their doors this spring, and it’s easy to see why. There’s an acute focus on quality in all they do; everything from the cabinet of steaks aging in the corner to the exotic housemade sausages signals carnivorous know-how to all who enter. 

They should study this sandwich at sandwich college.

But the sandwiches, oh, the sandwiches! One staff member focuses exclusively on making sandwiches with a degree of finesse you might otherwise only see at a sushi bar. Sandwich Research Associate had long been a fanboy of their New Canaan sandwich (a veritable meat parade with turkey, ham, roast beef, mayo, mustard, lettuce, tomatoes, and American cheese on toasted ciabatta), but that day, I wanted a single note. I went for the Burtis, with sliced rare roast beef, herbed mayo, lettuce, and tomatoes on ciabatta bread, and was summarily delighted. First, the bread is toasted just enough to snap and yield, but the nuance of the herbed mayo is what sold me. With roast beef, some joints might just throw rosemary or horseradish in there and call it a day, but this mayo is herbed with tarragon. It’s a quiet but confident pairing, a first-class upgrade on a transcontinental flight. As tailgating season begins, this is a welcome development.


A Tuna Melt at New Canaan Diner

As far as unsung town heroes go, the New Canaan Diner ranks right at the top. It’s a charming workhorse with a Restoration Hardware catalog-sized menu, fast-thinking

Melty, comforting diner fare.

staff, and, when we visited, an atmosphere bubbling with first-day-of-school kids being rewarded for good behavior with milkshakes. I had a once-in-a-decade hankering for a tuna melt, and there’s no place to answer that call quite like a diner. Sandwich Research Associate is utterly repulsed by tuna melts (his loss, honestly) and opted for a Reuben, but we were both in for a treat. 

Alongside our fountain Cokes, the sandwiches came exquisitely griddled with a side of golden fries. My melt was savory, well-constructed, and not too big, with white American cheese and the reassuring crunch of diced celery. His pastrami Reuben was a thing of beauty, not piled too high, but balanced and zingy, with plenty of sauerkraut. The rye wasn’t sopping with dressing, one thing that can make dressed sandwiches a frightening undertaking, and both sandwiches were modestly sized enough that we could get home and work through the afternoon without falling into a coma. Plus, when the lunch bill comes to $42, including a 25% tip, in New Canaan, you feel like you’ve won the lottery. 

The view from my fountain Coke


The Club Sandwich at Club Sandwich

Double-decker sandwiches always feel like a bad idea wrapped in a Dagwood comic wrapped in a 90s commercial about heartburn. I know they exist, but I’ve never been entirely sold on their need. When we were first married, I learned that Sandwich Research Associate was a longtime fan of the club sandwich and would order one from room service in every hotel we stayed in to gauge that hotel’s worthiness while I focused more on thread count and water pressure. In my previous opinion, all club sandwiches shred your mouth up to a Captain Crunch fare-thee-well with all those little toasty points and contain nap-inducing levels of bland sliced turkey. It’s not my scene.

Best club sandwich I’ve ever had. Note the double-turkeyfication

But Club Sandwich, the longtime Cherry Street staple for sandwich seekers, changed my tune. I’ve always loved their curry chicken and brie when I’ve nabbed it from luncheon sandwich trays, and I have dallied with their vegetarian Garden Wrap for months at a stretch. But, in the interest of typing the exact same words several times, there was no choice but to order the Club Sandwich Club Sandwich. It’s a different breed of club sandwich, on delightfully untoasted white bread (so soft! No need to file a class action lawsuit for your broken mouth!) with actually good sliced turkey (might be Boar’s Head Salsalito, but I forgot to ask) and shredded lettuce. I find shredded lettuce to be the ne plus ultra of sandwich greenery; it’s grippy, crispy, and absorbs whatever you throw at it. The friendly Club Sandwich crew is to be saluted for their craftsmanship; it may take me another decade to work through their extensive menu, but it’s a decade I look forward to. 


The New Canaan Stallion at Tony’s Deli

At every gathering, there’s a dark horse. Someone whose wild stories or shocking confessions you thrill to hear, and yet, you’re like, that guy? Tony’s Deli is that guy, a workaday staple, super popular with high schoolers and construction crews alike, offering a panoply of hot and cold sandwiches, salads, and nugget-cones-fries combos, doing a brisk business with folks who could be discussing anything from the Barbie movie to China’s debt problem.

Untamable: the New Canaan Stallion

Let’s talk about the sandwich. Sandwich Research Associate began reading the menu aloud, and five words, namely, “a scoop of potato salad,” caught my attention. I’d like to offer a tip of the hat to whatever individual, be they person or horse, who decided that potato salad might belong on a sandwich because it was the right idea. This ante-upper bills itself as “roast beef with a scoop of potato salad, coleslaw, horseradish, cheddar, bacon, onion, lettuce, tomato, cherry peppers, and mayo on a wedge.” It arrives the size of a newborn baby, weighty and precious. It could probably feed four adults. The horseradish and cherry peppers were the exact tart counterpart this little doughboy needed to come alive. It was a sandwich that, much like a wild stallion, initially appeared more foe than friend. But, sharing it, we emerged victorious, another feather in our caps and another few dozen miles needed to log this fall to work it all off. 


Sandwiches are a world unto themselves. The most memorable ones stay with you years later as waypoints on your life’s map. “Remember when we ate Al Ducci’s on that random golf course?” “What about when we took a Bay Cities Godmother on an 8 AM Southwest flight to Oakland?” The most ordinary ones fold into a blanket memory of a workplace, a parent, a neighborhood, or a grade school room. But their undeniable gift is the layered, golden ratio of carb to protein to flavor, to wherever you are right now. I’m not confident that we can, as a culture, get back to better wardrobe choices or stuff the toothpaste that is reality programming back into the tube of civility by simplifying our lunch choices. Still, the slow-down I enjoyed by inviting my own personal Cary Grant/  Sandwich Research Associate out on a few lunch dates was absolutely welcome. Cheers to all the square, rectangular, or wedge-shaped (if we must) meals in your future.

Congratulations on finishing a 2,300-word article about sandwiches! 

Alongside several far more interesting New Canaan folks, I’ll be guest bartending at Planet New Canaan’s Green Gala on September 14, 6:30 to 8:30 PM, at the Carriage Barn. I hope you’ll stop by to say hello, and help me support this wonderfully effective local nonprofit.

5 thoughts on “Who Knew: Taking the Eight Sandwich Challenge

  1. Another great article Laura! Thank you and your Sandwich Research Associate for continuing to remind us what a great town we live in!

  2. Sandwiches are one of the best things on the planet – love this idea and great writing! Will definitely be trying all eight!

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