Let's start by saying this: Every season is Milkshake Season. And there are plenty of seriously soul-satisfying shakes around town (even pumpkin spice to compliment this particular season), concocted with varying degrees of complexity, and these are 11 of the best.
New Territories, Pumpkin Spice Latte Milkshake, $12. (Scott Lynch / Gothamist)
New Territories: Gimmicky shakes started popping up everywhere after those tourist-trap monstrosities ruined the once quietly great Soho burger joint Black Tap. New Territories, however, is the only one who got the genre right. The key here is that they make their own ice cream, and it's always first-rate stuff. Plus the add-ons are well-deployed, and the architecture as a whole has integrity. So even a special like the Pumpkin Spice Latte shake pictured above (coffee and pumpkin ice cream, graham cracker dust, cinnamon chips, freshly made mini-cone, caramel and hot fudge drizzle) drinks and eats more like a good sundae than overwhelming sugar bomb.
Located at 190 Orchard Street just south of Houston (646-649-4521; newterritoriesnyc.com)
Petey's Burger, ChocoBerry, $5. (Scott Lynch / Gothamist)
Petey's Burger: A loudly-colored burger joint with food that's always better than you expect (and, at the LIC location anyway, plays movies and sports with the sound on), Petey's whips up an absolutely perfect no-fuss shake. The ice cream is random-brand, the syrup industrial strength, but the ratios are dead-on, and your counter worker seems to know the exact right amount of time to stick in the mixer for a wonderfully thick beverage. The ChocoBerry, in particular, is amazing.
Located at 46-46 Vernon Boulevard in LIC and 30-17 30th Avenue in Astoria (peteysburger.com)
OddFellows, Cold Brew Milkshake, $9. (Scott Lynch / Gothamist)
Sam Mason's ever-expanding ice cream chain (he and his partners Holiday and Mohan Kumar just opened a fourth parlor in Dumbo) is always an excellent choice for all of your ice cream needs, but lately I've become something of an OddFellows Cold Brew Milkshake addict. This invigorating and wonderful concoction swaps out milk for actual coffee, with a whopping three scoops of ice cream mixed in. The flavors are your choice, but get one of the coffee ones, like with chocolate "crunch," or coconut, or caramel, and you'll be flying for hours.
Located in the East Village, Nolita, Williamsburg, and Dumbo (oddfellowsnyc.com)
Harlem Shake, Salted Caramel, $5. (Scott Lynch / Gothamist)
Harlem Shake: The retro-styled burger joint and the video-meme dance craze hit at about the same time back in 2013, but only one is still going strong. No surprise, it's the one with the delicious milkshakes. The Harlem Shake shakes are straightforward (the syrup does a lot of the work), super sweet in a good way, and possibly the thickest in town. The signature Red Velvet one is great, as is the classic Black and White, but I always come back to my personal favorite, the Salted Caramel. The food here hits the spot as well.
Located at 100 West 124th Street at the corner of Lenox Avenue (212-222-8300; harlemshakenyc.com)
Do, Salty and Sweet, $9. (Scott Lynch / Gothamist)
DO: Okay, hear me out. The raw cookie dough they sell scooped into cones like ice cream at this insanely popular touristy spot are so sugary they're almost impossible to eat plain. But when you plop one into a shake, cut it with vanilla ice cream and (in the case of the Salty and Sweet I sucked down in Washington Square Park recently) mix it with salted caramel and dark chocolate chips, it actually makes for a well-balanced treat. I mean, it's still sweet, but it's more like normal-dessert sweet.
Located at 550 LaGuardia Place between West 3rd and Bleecker Streets (646-892-3600; cookiedonyc.com)
Ray's Candy, Nutella Shake, $8. (Scott Lynch / Gothamist)
Ray's Candy: Everyone loves Ray's, the gloriously chaotic 24-hour snack shop that's been feeding the East Village since 1974. But remember, we are all obligated to actually go there and buy stuff (and say hi to the now-85-year-old Ray), if we want it to be around forever. There's a lot going on here, food-wise—fried Twinkies! chili cheese dogs! fish-n-chips! hot caramel sundae!—but the best thing on the menu might be Ray's Nutella Shake, which is just vanilla soft serve with a hefty dollop of the chocolate-hazelnut spread blended in. It is completely wonderful exactly as is.
Located at 113 Avenue A between St. Marks and 7th Street (212-505-7609)
Milk Bar, Crunchy Cereal Babyshake, $6. (Scott Lynch / Gothamist)
Milk Bar: The great Christina Tosi has built a vast empire on the shoulders of her Crack Pie and Compost Cookies, neither of which, sadly, are as good today as when she was baking them herself at the back of Ssam. No matter! Tosi's ice cream is still reliably first-rate, and Milk's milkshakes retain her signature mad-genius, delicious charm. The Crunchy Cereal is the one to get, made from Tosi's Cereal Milk soft serve and topped with buttered and roasted corn flake crumbles. It's like sucking down the world's greatest Saturday-morning-cartoon breakfast.
Five Guys, Salted Caramel, $4.99. (Scott Lynch / Gothamist)
Five Guys: This North Virginia import has settled in nicely here in the big town, with some 20 locations across all five boroughs. The food can be hit or miss—keep your expectations low and you'll do fine—but the milkshakes are consistently satisfying in that addictive, slightly fake-tasting way. They tend to be less thick than most, so you can really gulp 'em down. Salted Caramel's my usual, but mix-ins to the base vanilla include bananas, Oreos, cherry, and bacon.
Twenty locations throughout the city (fiveguys.com)
Rip's Malt Shop, Coffee with brownies and caramel, $9.50. (Scott Lynch / Gothamist)
Rip's Malt Shop: One of my favorite new counter-service restaurants this year has to be Rip's, which specializes in vegan versions of diner classics (the "tuna" melt special right now is fantastic) and features a pleasant backyard dining area. There's always a few flavors of Van Leeuwan's dairy-free ice cream available here, and you can have a scoop or three served as a sundae with a wide variety of tempting toppings, or get a shake and drink your dessert with dinner, like I did with this coffee and caramel sauce and brownie bits beauty.
Located at 10 Clermont Avenue just south of Flushing (347-689-9009; ripsmaltshop.com)
Shake Shack, Salted Caramel, $5.29. (Scott Lynch / Gothamist)
Shake Shack: For a hugely successful international chain that literally has "shake" in its name, you don't hear a lot of hype about their eponymous frozen treat. Which is fine with me; it keeps the beverages-only "C-line" short at the packed-since-2004 mothership in Madison Square Park. The only downside to getting your shakes here (and at the two other chains on this list): the calorie count of your drink—in the case of my most recent Salted Caramel, a whopping 730—is right there staring you in the face when you order. Totally worth it though.
There are 22 Shacks in NYC (shakeshack.com)
Van Leeuwen, Salted Caramel and Coffee, $8.50. (Scott Lynch / Gothamist)
Van Leeuwen: Recent, rapid expansion is perhaps to blame for some unfortunate inconsistencies lately at this decade-old operation—and why are special flavors still sold out all the time?—but my well-crafted Salted Caramel and Coffee shake at the Williamsburg outlet last week gives me faith that they'll sort things out. Or at least I hope they will, because this is one my overall favorite parlors, and one of the few with the equipment and the flavors appropriate for a really great classic shake.
The are now 11 Van Leeuwens in Brooklyn and Manhattan (vanleeuwenicecream.com)
(Note: Several of the city's best ice cream parlors aren't mentioned here because they don't even offer them (Ice & Vice and Malai, for example), and at other top spots (Morgenstern's) you're better off enjoying your dessert in non-beverage format.)