New Canaan’s Top-10 Sandwiches


There is an amazing ratio of sandwiches to people here in New Canaan. So amazing, that a couple of places (most notably the Best Würst and the Forest St. Deli) closed while we compiled this list. It’s important to note that this specific list was relegated to counter service restaurants or delis only. We are well aware of many of the amazing sandwiches that are served at traditional sit-down restaurants here in town. We’ll save those for another time. For now, we hope you enjoy this list—sorted alphabetically—of our top-10 sandwiches in New Canaan. Feel free to comment below to weigh in if we missed your favorite, and be sure to click on the links to our business directory where you can add your own ratings and reviews.

The College Wrap, Chicken Joe's. Credit: Terry Dinan

The College Wrap, Chicken Joe’s. Credit: Terry Dinan

Chicken Joe’s – The “Home of the High School Special” is also home to some terrific, inventive sandwiches and wraps. With all due respect to my bud Kevin—a big fan of the “Electrician’s Combo” (Chicken Cutlet, Fresh Mozzarella, Lettuce, Mayo, Oil, & Vinegar)—we were partial to the popular “College Wrap” ($7.50) which combines the signature chicken nuggets, potato cones, American cheese and honey mustard in a flour tortilla.

The #29 Wrap, Club Sandwich. Credit: Terry Dinan

The #29 Wrap, Club Sandwich. Credit: Terry Dinan

Club Sandwich Anyone who lived in New Canaan in the mid-80’s knows Club Sandwich. In business since 1986, this Cherry Street staple took the town by storm with its numeric, categorized menu featuring more than 45 sandwiches and wraps. The one that most New Canaan old timers will remember is the #29 Wrap ($6.99), an often-imitated, never-duplicated concoction of smoked turkey, bacon, apple butter, lettuce and mayo on a four tortilla. It’s a true New Canaan original, just like the place that serves it.

Meatloaf Special, CT Sandwich Co. Credit: Terry Dinan

Meatloaf Special, CT Sandwich Co. Credit: Terry Dinan

CT Sandwich Co. Eugene Chun’s Pine Street shop has quickly become a popular destination for hungry New Canaanites, with a unique lineup of offerings made from gourmet ingredients. And while the sweet and spicy chicken sandwich gets most of the headlines, it’s the meatloaf sandwich ($10) that has caught our attention of late. Taking comfort food to a new level, a healthy dose of tender, flavorful meatloaf is smothered with caramelized onions, melted fontina cheese and garlic mayo. The grilled country bread holds up nicely and provides a nice, crispy contrast to the rest of the sandwich. Currently classified as a “special,” we are lobbying Chun to make this a permanent part of the menu.

The Eclectic Cheeseteak. Credit: Terry Dinan

The Eclectic Cheeseteak. Credit: Terry Dinan

Eclectic Situated well off the beaten path on Vitti Street, chef/owner Robert Milano’s gourmet establishment showcases some innovative, New American cuisine that has garnered well-deserved critical praise in its year-plus of operation. We sampled—and loved—the Eclectic Cheese Steak ($10), which features real shredded steak (as opposed to the ubiquitous “steak-umm” product frequently seen in these parts), sautéed mushrooms and onions, Havarti cheese, scallions, honey ham, sweet, peppers and aioli on grilled bread.

Italian-Style Pepper & Egg, Joe's Pizza. Credit: Terry Dinan

Italian-Style Pepper & Egg, Joe’s Pizza. Credit: Terry Dinan

Joe’s Pizza Serving generations of New Canaan families for more than four decades, Joe’s is not only a great place for pizza and wings—they also have a terrific sandwich menu. And while many will go for the flashy choices like the Cluck N’ Russian (chicken cutlet, bacon, swiss, lettuce, tomato, Russian dressing), we like the simple, traditional Italian Style Pepper & Egg grinder ($6.99). With eggs & peppers perfectly cooked and served on a buttered, grilled wedge, it’s also the sandwich of choice of New Canaan First Selectman Rob Mallozzi as well as owner Lorenzo Colella’s neighbors at the New Canaan Fire Station. Now those are impressive referrals.

The BBQ Pulled Pork, Rosie. Credit: Terry Dinan

The BBQ Pulled Pork, Rosie. Credit: Terry Dinan

Rosie – It’s tough to look past the amazing breakfast/brunch items on Rosie’s menu, but if you can muster up the willpower to do so, give the pulled pork sandwich ($12, served with fries) a shot. A huge helping of sweet, tender BBQ pork accompanied by a healthy dose of spicy, colorful firecracker slaw packed onto a delicious brioche roll, this sandwich is literally a head-turner as you have to crane your neck in different directions to eat it. After one bite, you’ll know it’s well worth the extra effort.

The Big Kalooski, Silvermine Market. Credit: Terry Dinan

The Big Kalooski, Silvermine Market. Credit: Terry Dinan

Silvermine Market – Perhaps New Canaan’s best-kept secret, this quaint little emporium nestled in the middle of a largely residential area on the New Canaan-Norwalk line features a surprising sit-down dinner transformation on Friday and Saturday nights. That said—it’s best known for its hearty breakfast and lunch menus, featuring dozens of clever sandwich combos. Appropriately listed as #1 on the menu is the Big Kalooski ($8.50), a simple-yet-delicious blend of hot roast beef, melted Swiss, A-1 Steak Sauce on a toasted garlic wedge.

The Manhattan Club, Walter Stewart's. Credit: Terry Dinan

The Manhattan Club, Walter Stewart’s. Credit: Terry Dinan

Stewart’s Market – A New Canaan institution for more than a century, Walter Stewart’s has seen many a competitor come and go. The reason for its success is good, old-fashioned customer service coupled with an uncanny ability to evolve with the times. One example is the Stewart’s deli, which goes beyond the standard supermarket-style of “take a number” and offers a terrific menu of sandwiches, Panini and wraps—all made with care by an extremely friendly and efficient staff. Our choice was the delicious and filling Manhattan Club ($6.99), featuring a combo of hot pastrami and corned beef, topped with melted Swiss, Russian dressing and coleslaw served on a Portuguese roll. It’s the Stewart family’s way of bringing a little bit of NYC to New Canaan.

Chicken Cutlet Cordon Blue, Tony's Deli. Credit: Terry Dinan

Chicken Cutlet Cordon Blue, Tony’s Deli. Credit: Terry Dinan

Tony’s Deli A hotspot for teens and families seeking a quick fix, Tony’s is justifiably jammed throughout the day with fans clamoring over a menu dotted with dozens of intriguing choices. And while many will cry foul over looking past the famous Joe Co. wrap (chicken cutlet, potato cones, bacon, Monterey Jack, avocado, lettuce, tomato, honey mustard), we’re going to go with the Chicken Cutlet Cordon Blue ($8.79). A breaded, fried chicken breast covered with blue cheese dressing, melted American, ham, lettuce and tomato, this is a filling, delicious take on an old favorite. It’s also the sandwich of choice of New Canaan’s 6’6, 243-lb., Boston College-bound football star Zach Allen. And we’re not going to be the ones to argue with him.

The "Macho Man", Dinan's Deli. Credit: Terry Dinan

The “Macho Man”, Dinan’s Deli. Credit: Terry Dinan

Dinan’s Deli – OK, so we don’t actually have a deli, but we took some liberties to pay homage to our dad, Tim Dinan. Born and raised in the Bronx, dad has many fond memories of local NYC delis and the amazing sandwiches they served “back in the day.” One day, our old man took it upon himself to create his own sandwich, consisting of liverwurst, horseradish cheddar, Bermuda onion, beefsteak tomato, Dijon mustard on pumpernickel bread. He called it “The Macho Man”(ingredients cost about $14 at the supermarket, yielding two sandwiches), and true to its name, it packs quite a punch. All nepotism aside, it is really a great sandwich, ingeniously interspersing bold flavors and textures, with the juicy tomato and smooth liverwurst perfectly balancing out the horseradish cheese and crisp onion, and the mustard giving it a little extra kick at the end. Dad was so high on this sandwich he (unsuccessfully) implored our restaurateur uncle Terry to put it on the menu—first at the ‘21’ Club, then at his eponymous restaurant at 34th & Park. So while it never gained notoriety in the NYC power lunch scene of the 1980s, Mike and I wanted to give a tip of the cap to our dad by ensuring The Macho Man’s place in history here on

3 thoughts on “New Canaan’s Top-10 Sandwiches

    • Alan!! So glad to see you chiming in! My life would be different, I am sure, if not for you and your leadership at NCHS (Class of 76-77)

  1. Going to Stewart’s for that sandwich. How has that been under my nose all these years? My vote for No. 1 on this list is CT Sandwich’s meatloaf, it’s a delight.

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