10 Majorly Upgraded Ice Cream Sandwiches

The ice cream sandwich is one of the most nostalgic and iconic of all dessert treats. After all, it’s basically two desserts in one—cookies (or a strangely cookie/wafer-like substance) and ice cream—that makes it doubly enticing for kids (and certain adults) who would normally be cruelly forced to choose between one and the other. I can remember being presented with this delicious treat in so many situations: afternoon snack time on a hot day at summer camp, a surprise retrieved from deep freeze after dinner at home, even occasionally the reward for chasing the siren call of the ice cream truck down the street. There was nothing better.

In the old days, ice cream sandwich choices were limited. There was the classic rectangular Good Humor-style sandwich, consisting of two weirdly pasty soft chocolate wafers pockmarked with indentations surrounding delicious artificial vanilla ice cream. Then there was the Chipwich and its many variations; two soft chocolate chip cookies surrounding a mound of vanilla or chocolate ice cream. Sadly, Nestlé killed off the original Chipwich in 2009, although imitations of varying quality can be found in gas stations and grocery stores nationwide.

Things are different these days, and the humble ice cream sandwich has been elevated above and beyond our wildest prepubescent dessert fantasies. For better or worse (but mostly better), bakers, savants of sweet, and ice cream connoisseurs have come up with endless delicious variations. Here’s a list of some favorites, so go ahead and treat yourself.

Black and White Cookie Sandwich – Ample Hills Creamery/Baked, NYC

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This is collaborative effort between Ample Hills Creamery, purveyor of Brooklyn’s finest ice cream, and Baked, a tasty bakery and coffee shop with locations in both Manhattan and Brooklyn. The idea is so simple that one can’t help but wonder why no one has done this before (if they have, it hasn’t taken off like this): take a black and white cookie, a culinary symbol of NYC if there ever was one, and stuff it with vanilla malted ice cream ringed with a sprinkling of malted chocolate Rice Krispies crunch. As Seinfeld once so wisely told us, look to the cookie!

Negroni Ice Cream Sandwich – Pearl & Ash, NYC

Pearl & Ash

Looking for something on the boozy end of the spectrum? NYC’s Pearl & Ash restaurant has the answer. This Nolita establishment offers up a take on the classic Negroni cocktail—Campari, gin, and vermouth-infused ice cream encased by two vanilla-orange wafers. Visually, this was clearly influenced by the classic Good Humor ice cream sandwich, but it’s definitely not for kids.

DKA Ice Cream Sandwich – Dominique Ansel Bakery, NYC

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Dominique Ansel is best known for starting the Cronut craze, with lines still stretching around the block outside his Soho bakery as the hopeful often hopelessly try to get a taste of the legend. But when the Cronuts run out, try this off-menu treat—a Kouign-amann (a kind of buttery cake from Brittany, France) packed with vanilla ice cream. It’s kind of like a cream puff, but much more substantial and it doesn’t take any shit.

Coolhaus Ice Cream Sandwich Truck- NYC, LA, Dallas

Coolhaus

Coolhaus ice cream trucks roam the streets in only three cities and are inspired by architectural influences that you can read more about on the company’s website, but we’re here to discuss their ice cream sandwiches. You can pick and choose from a dizzying array of options—how about the fried chicken and waffles ice cream (coming soon) in between two maple flapjack cookies? Or maybe the “Netflix” ice cream (white cheddar popcorn infused with Doritos) packed into a marble rye cookie? Yes, please. Check out your local Whole Foods for some pre-packaged options as well.

“The Original” Churro Ice Cream Sandwich – Churro Borough, Los Angeles

Churro Borough

Tucked away in the Los Feliz neighborhood on LA’s eastside, and sporting a “small-batch” philosophy, the dessert shop Churro Borough offers a Mexican-influenced take on the ice cream sandwich that places your choice of ice cream in between two fried churro discs sprinkled with spiced sugar. They tend to run out, so get there early.

Funnel Cake Ice Cream Sandwich – Quenelle, Los Angeles

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Sadly, the home of this fairground favorite version of an ice cream sandwich, Ice Que, closed its doors at the end of July. However, rumor has it that one of its two sister shops, Quenelle, located in Burbank and San Marino, may be bringing it back… Let’s hope so, because greasy tube-squeezed funnel cake with an ice cream heart needs a home somewhere.

Doughnut Ice Cream Sandwich – Firecakes Donuts, Chicago

Firecakes Donuts

Speaking of fried dough, Chicago’s Firecakes Donuts is giving the people what they want with a straightforward concept: a doughnut split down the middle and packed with either vanilla or pistachio ice cream, finished with a little chocolate sauce just for good measure. Simple? Yes. Delicious? Presumably.

Tipsy Scoop Ice Cream Sandwiches – various locations

Tipsy Scoop

This company has a plethora of alcohol-infused ice cream flavors, including strawberry rhubarb bourbon, red velvet martini, and “hot” buttered rum. In NYC, you can pick up a pack of a dozen ice cream sandwiches made from chocolate chip cookies and both Frangelico affogato ice cream and cake batter vodka martini ice cream.

The Red Monstah – The Cookie Monstah Food Truck, Boston

The Cookie Monstah

This ice cream sandwich truck traverses the mean streets of Boston most days, and provides the ice cream-deficient with 14 different versions of the classic. But a standout has to be The Red Monstah—two red velvet cookies crammed with mint Oreo ice cream, comprising what is surely the prettiest ice cream sandwich you can find.

Blackberry/Tangerine Shortbread Ice Cream Sandwich – Leona’s Ice Cream Sandwiches, Pittsburgh

Leona’s

Blackberry balsamic and tangerine ice cream topped with blackberry preserves on a shortbread cookie with cardamom sugar…this is a summer ice cream sandwich through and through. You have to travel to Pittsburgh to grab this, along with Leona’s Ice Cream Sandwiches; other interesting flavors like Luxardo Cherry/Chocolate Fudge.

Jonah Flicker lives in Brooklyn, NY and covers travel, food, film, whiskey, and other spirits for a variety of publications. You can follow him on Twitter @illiotgould.