Crumbl, Insomnia and more: A food critic's guide to popular cookie chains

Cookies from Duchess Crumbl stores on Long Island. Credit: Stephanie Foley

Every time we turn around, it seems like another jumbo cookie chain has landed on Long Island: Crumbl, Insomnia, Chip City. From the three Duchess Cookies outposts to the original cookie mecca Levain Bakery in Wainscott, serious sugar highs await.

Long Island’s cookie trend really took off during the pandemic, when bakeries and home cooks pivoted to drool-worthy, Instagram-friendly cookies that could be ordered by sweet-toothed patrons — picked up or delivered — no contact required. Then came the franchises.

Retail cookie chains aren’t new phenomenon — remember Mrs. Fields? What about David’s Cookies? Enter TikTok and Instagram: Today's brands have grand social media presences fueling their growth, along with rotating flavors, incentivized loyalty programs and flash-specials. But it's confusing to tell one massive cookie from another. Cookie aficionados know some chains serve warm-from-the-oven cookies, others do made-to-order combinations, while many sell a merry-go-round of flavors that change weekly. There are stuffed cookies, thin cookies — all have dedicated fans.

In the spirit of embracing Long Island cookie-mania, here is a field guide to each of the chains, with critic's picks for the best options when visiting.

Insomnia Cookies

730 Fulton Ave., Hempstead

Founded at the University of Pennsylvania in 2003 by an insomniac looking for sweet, warm, dorm-delivered late-night munchies, Insomnia Cookies has grown to more than 260 locations nationwide with the brand’s first Long Island bakery in Hempstead. Offering pickup, delivery and shipping options until 1 a.m. (3 a.m. on weekends), Insomnia sells warm, addictive cookies including classics such as chocolate chunk and oatmeal raisin, favorites (snickerdoodle and confetti) and cult favorites (red velvet and peanut butter chip). There are vegan cookie options, and a gluten-free chocolate chip. Ice cream combos can be built with flavors like spicy hot chocolate to top cookies, brookies, brownies and blondies.

Top picks: If you like peanut butter, the deluxe Reese’s topped peanut butter cookie is the winner here. Served soft and warm, the chocolate melty, it tastes like eating a tablespoon of peanut butter out of a jar (otherwise known as heaven for peanut addicts). A close second: the deluxe salted caramel cookie, which contains pieces of buttery toffee, swirls of caramel and crunchy sea salt for texture and topping.

More info: Classic regular size cookies start at $2.95, deluxe jumbo cookies at $4.95, and a pack of 12 Little Dipper minis starts at $10.50; insomniacookies.com

Insomnia Cookies specializes in jumbo treats.

Insomnia Cookies specializes in jumbo treats. Credit: Insomnia Cookies

Chip City

1948 Jericho Tpke., East Northport; 951 Franklin Ave., Garden City; 280 Main St., Huntington; 1240 Deer Park Ave., North Babylon; 3458 Long Beach Rd., Oceanside; 2012 Merrick Rd., Merrick

Started by childhood friends Peter Phillips and Teddy Gailas in Astoria, Queens, Chip City has quickly grown from an Oceanside store that opened in 2022 to six Long Island locations. At Chip City, patrons can take cookie-fueled selfies under neon lights with “have a gooey day” messages. Nearly 40 rotating flavors including core favorites — chocolate chip, cookies n’ cream, and a decadent mocha — and fun cookies such as a vibrant purple-and-blue frosted wild berry strudel, Fluffernutter (a sugar cookie loaded with peanut butter chips and marshmallow cream) and a dairy-free chocolate chip cookie that is always on the menu.

Top picks: The original chocolate chip cookie here is killer, a brown sugar cookie with just the right amount of sweetness and dark chocolate. The dairy-free chocolate chip is equally great, you will barely notice a difference. Non-chip faves? The PB&J, which tastes like a trumped up peanut butter and grape jelly sandwich, and the subtly addictive mocha, a coffee-flavored cookie laced with chocolate chips.

More info: Cookies, which start at $4.50, are best served with milk, so Chip City offers an assortment (whole, skim, almond, oat, chocolate) starting at $3.25), as well as coffee ($2.75) and espresso; chipcitycookies.com

Cookies and cream and stuffed Nutella sea salt cookies from...

Cookies and cream and stuffed Nutella sea salt cookies from Chip City in Oceanside. Credit: Joann Vaglica

Thin Cookies 

425 Jerusalem Ave., Hicksville

Zohal Raja of Hicksville “used to buy Tate’s cookies all the time.” Until her husband asked if she could try to make a softer version. Raja nailed them and Thin Cookies was born. As the pandemic progressed, Raja quit her day job, outgrew her home kitchen, graduated to a shared incubator kitchen space, and finally opened the Hicksville retail store that sells three regular cookie flavors: chocolate chip, double chocolate chip — and Snickerdoodle, a cinnamon sugar cookie that “didn’t feel as obvious,” with its nostalgic, warm flavoring. She recently debuted monthly flavor drops. February’s featured flavors Funfetti, cookies and cream, and red velvet. The cookies — paper thin and light, chewy and soft on the inside, crisp on the outside — are a refreshing departure from the market-saturated jumbo stuffed cookie trend.

Top picks: The snickerdoodle here is the bomb, light and airy, loaded with cinnamon, it’s hard to eat just one. But if you’re a Tate’s fan, you will love the chocolate chip, which is a wonderful counterpart to the fat, full chocolate chip cookies offered by most.

More info: Cookies are $7 for six, $13 for 12 and $25 for 24; thincookiesny.com

Chocolate chip cookies at Thin Cookies in Hicksville.

Chocolate chip cookies at Thin Cookies in Hicksville. Credit: Aisha Khwaja

Crumbl Cookies

3511 Hempstead Tpke., Levittown; 20 Soundview Market Place, Port Washington; 2104 Merrick Ave., Merrick; 5500 Sunrise Highway, Massapequa

First Levittown, then Port Washington, then Massapequa, Crumbl Cookies has rapidly expanded across Long Island, with the latest opening in Merrick. A social media phenomenon that began in Utah, Crumbl's cookies garner a lot of hype in the sweet space — they both look and feel indulgent. Stores are anchored by a spare pink and white open kitchen and self-ordering kiosks — and offers a weekly rotation of six flavors that could include any combination of chocolate chip, Rice Krispie, pink frosted sugar, and double chocolate chip, while specialty flavors might include cornbread, Key lime pie, peppermint bark, caramel popcorn, buttermilk pancake, a cakey apple cider muffin, strawberry milkshake topped with a Pirouline cookie, or sea salt toffee.

Top picks: The beauty of Crumbl Cookies is their soft, silky texture and understated sweetness, making their sugar cookie a winner. Topped with a subtle, pastel pink frosting, they’re hard to beat, but get some competition from the confetti cookie, another sugar confection chock full of rainbow sprinkles and a dollop of white frosting that the kids will go bananas over.

More info: Cookies are $5 each, with party boxes of 12 running $42. Flavor drops happen weekly on Sundays at 8 p.m.; crumblcookies.com

The opening cookie assortment at the new Crumbl Cookies in...

The opening cookie assortment at the new Crumbl Cookies in Massapequa. Credit: Newsday/Marie Elena Martinez

Duchess Cookies

331 S. Oyster Bay Rd., Plainview; 3567 Long Beach Rd. Oceanside; 630 Old Country Rd. Garden City in Roosevelt Field mall

While many of the cookie chains offer stuffed cookies as specialty flavors, Duchess Cookies is the shop to hit if you like your cookies stuffed all the time. These are the heaviest cookies on this list and Duchess offers the most daily variety in terms of flavors. These swanky, hot pink, black and white shops — dotted with trendy Lucite tables and selfie walls — display a whimsical rainbow of cookies behind glass. From the red unicorn (sugar-filled with strawberry cheesecake) to the Cookie Monster (blue sugar cookie with a chocolate cookie tucked inside) to the purple and pink cotton candy tie-dye cookie sprinkled with edible, silver glitter, this place is a wonderland for kids. Flavors include confetti and s’mores, chocolate chip walnut, even a Rice Krispie cookie, but feel less fanciful here because of the creative selection. It’s hard to compete with churro Nutella and banana nut cookie butter.

Top picks: The oatmeal apple pie is the quintessential oatmeal cookie with its breakfast bar vibes and chewy apple pie filling. Second to that, if Nutella’s your thing, the churro Nutella is beyond compare.

More info: Cookies are $4.50 each, and if you buy six, you get one free; duchesscookies.com

Duchess Cookies.

Duchess Cookies. Credit: Oksana Pali photography

Levain Bakery

354 Montauk Hwy., Wainscott

The O.G. of oversized cookies, Levain might be responsible for the entire jumbo cookie trend. Launched in Manhattan in 1995 selling bread, the bakery's owners — runners fueling their carb addiction — came up with a fist-sized chocolate chip walnut cookie that has been delighting New Yorkers for decades. The Wainscott store became a must-stop en route to the farther shores of the Hamptons during the summer and their cookie selection expanded to include the signature four: chocolate chip walnut, dark chocolate chocolate chip, oatmeal raisin and dark chocolate peanut butter chip. Two newer additions: a two-chip chocolate chip (sans nuts) and coconut caramel chocolate chip. The shop also sells vegan and gluten-free chocolate chip walnut options.

Top picks: Levain does chocolate like nobody else, so both of the dark chocolate varieties — chocolate chocolate chip and peanut butter chip — are deep and decadent, wholly irresistible for chocolate lovers. But don’t sleep on the new coconut caramel chocolate chip, the underrated meeting of macaroons and chocolate chip cookies, a personal favorite.

More info: Cookies are $5.25 in-store, but can be ordered online as 4-, 8-, and 12-packs for $29, $49, and $79 if you’re not headed out to Wainscott. levainbakery.com

Levain Bakery.

Levain Bakery. Credit: Levain Bakery