Hopsicle ($5)

Sure, frozen beer isn’t so tasty when you’ve accidentally left it on the fire escape in December, but come the sweatiest month of summer, you might find it more appealing. This surprisingly tasty frozen can is peeled back and topped off with a tequila rinse, most delightfully enjoyed in the Mexican saloon’s 30-seat garden.
Diablo Royale Este 167 Ave. A bt 10th & 11th Sts. (East Village) 212.388.9673

Bourbon Street Milkshake ($12)

The Blue Ribbon brothers bring you a grown-up childhood treat that would make your mama faint: a glass teeming with ice-cold chocolate milkshake laced with sweet, sweet bourbon and a heaping spoonful of creamy Nutella. Just be sure to thank the barkeep and brush your teeth before bed.
Brooklyn Bowl 61 Wythe Ave. @ N. 11th St. (Williamsburg) 718.963.3369 

Milkshakes with a Shot ($11)

This old-school American diner gives classic flavors a kickin’ update by adding heaps of hard stuff to knock you off your stool. Cookies and cream gets creamier with the addition of Coole Swan Irish Cream, while the "Campfire" (a combo of house-made toasted marshmallows and vanilla ice cream) gets extra smoke from Woodford Reserve.
Bills Bar & Burger 22 9th Ave. @ 13th St. (Meatpacking) 212.414.3003 

Milkshake Shot ($3)

For a tiny tipple of frozen, creamy goodness, snag this caramel-flavored milkshake shot (a more potent version of your favorite childhood treat that’s bursting with Maker’s). The alcohol content is nothing to balk at, but they’re still small (and surprisingly affordable!), so go ahead and have two.
The Stanton Social 99 Stanton St bt Ludlow & Orchard Sts. (Lower East Side) 212.995.0099 

Spiked Milkshake ($11)

With five options for ice cream intoxication, this burger joint has a concoction for every persuasion, including a tequila-based Azteca Mocha (tequila, coffee ice cream, cayenne pepper and chocolate syrup), the ultra-vanilla Shocker (vanilla vodka, vanilla ice cream and Oreo cookies) and choc-overload Night Rider (Kahlua, chocolate liqueur, Oreo cookies and chocolate ice cream).
BLT Burger 470 6th Ave bt 11th & 12th Sts. (Greenwich Village) 212.243.8226 

Tequila Snocones ($4)

When it’s so hot that nothing will cut it but actual ice, spike your frozen chips with the most dangerous of sauces: tequila! Forget your usual cherry and grape flavs, choose instead from exotic fruits like lime, mango and blueberry-pomelo as well as vanilla and a cinnamon-flavored rice milk known South of the Border as horchata.
Cantina by Cascabel 1542 Second Ave. @ 80th St. (Upper East Side) 212.717.7800 

Cocktail Inspirations ($12)

Indecisive sallies needn’t fret at this Spanish tapas spot, where a single order of the “cocktail inspirations” gets you a ginger beer-based dark and stormy ice cream float, a tangy frozen margarita and a vanilla milkshake sauced with bourbon.
La Fonda del Sol 200 Park Ave @ 43rd St. (Midtown West) 212.867.6767 

Sarsaparilla Soda Float ($9)

Forget root beer—this float replaces your usual corn-syrupy concoction with all-natural cane-sugar sweetened sarsaparilla and a healthy dose of locally-distilled Hudson Baby Bourbon Whiskey. Top that concoction with a slug of Guinness, two heaping scoops of vanilla and a maraschino cherry, and only one question remains: spoon or straw?
Nios 130 W. 46th St. bt 6th & 7th Aves. (Midtown West) 212.485.2999 

Port Granita ($7)

This port-based Italian ice is crafted for more than 24 hours before it's shaved into heaping pink scoops for your spooning pleasure. With ingredients like plum, cinnamon, pepper and ginger, you wont believe there’s still five months till Christmas.
Silverleaf Tavern 70 Park Ave. @ 38th St.  (Midtown) 212.973.2550

Buzzed Mochi (two pairings, $10) 

The alcohol content in this treat is low, but the fancy dessert scores major points for originality and flava. The ice cream finger food (made possible by wrapping the frozen confection in pounded sticky rice) comes in six flavors, each perfectly paired with boozy sauces for dipping. For absolute indulgence, try the dark chocolate espresso drenched in Irish crème and the strawberry sort doused in dark chocolate Chambord ganache. 
Koi 40 W. 40th St. bt 6th & 7th Aves. (Midtown West) 212.921.3330  

Southern Sundae ($12)

This new addition to Flex's dessert repertoire features vanilla ice cream that's been hand-spun with raw bourbon for extra kick, then piled atop red velvet cake from Pastry Chef Zac Young. This happy marriage is then drizzled with peach caramel and candy pecans for a treat that's as sweet and dangerous as a prom-bound Southern Belle.
Flex Mussels 174 E. 82nd St bt Lexington & 3rd Aves. (Upper East Side) 212.717.7772

Tequila Snowcone ($8)

This high-end tequila den is best known for its bottle-storing lockers, but these days they've got another sneaky trick up sleeves: tequila snowcones. Enjoy your juvenile treat in grown-up flavors like hibiscus and tamarind. The sign may say "biblioteca," but your heart will say "fiesta."
Zengo & La Biblioteca 622 3rd Ave. @ 40th St. (Midtown East) 212.808.8110