On September 19, 2026, Loser’s Eating House and OREO cookies will drop a one-day-only The Big OREO Roll at First Taste 001 in Williamsburg. This collab turns a cult-favorite cinnamon roll into an OREO cookie-packed centerpiece that exists for one afternoon on one rooftop. Here is what the drop is, who is behind it, and how to lock in your chance to try it.
1. The Drop At A Glance
The Big OREO Roll is a large-format OREO cookie version of Loser’s signature cinnamon roll. It uses the same sourdough brioche base, then layers in Oreo cookie chunks in every creviec. The roll appears only at First Taste 001 on September 19, 2026, in a limited batch.
First Taste 001 takes over the LilliStar rooftop at the Moxy Hotel in Williamsburg for one afternoon. Three one-day-only food drops anchor the event, including The Big OREO Roll. Guests buy a ticket to enter, then purchase each drop onsite while supplies last.
2. The Collab: Who’s Behind It
Loser’s Eating House is a pastry pop-up built around its cult-favorite cinnamon roll and earned last year’s 8it Award for “Best Pastry Pop-Up”. The pop-up originally sold its rolls on Monday nights at Jean’s before the operation moved to a takeout location in Hudson Square. The following grew around a single, obsessively executed product.
OREO brand is one of the most recognized cookie brands on the planet. According to brand owner Mondelēz International, more than 60 billion Oreo cookies are sold each year in over 100 countries. Guinness World Records has certified OREO brand as the world’s biggest-selling cookie. That global scale sets the stage for a rare, small-batch collaboration.
This drop focuses on a single rooftop for one afternoon. That local focus started with a question 8it asked every chef participating in First Taste 001: Who is your dream collab? For Lizzy Koury of Loser’s Eating House, the answer was immediate: “I grew up eating Oreos, and I’ve wanted to put them in our roll since day one. Getting to actually do it with Oreo is surreal.”
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3. What Is The Big Oreo Roll At Loser’s Eating House?
The Big Oreo Roll is an OREO cookie-loaded take on Loser’s Eating House’s signature cinnamon roll. It is built on the same sourdough brioche base and finished with Oreo cookie chunks. The roll is exclusive to First Taste 001 on September 19, 2026, in limited quantity, and appears only at this event.
The dough is the same sourdough brioche base that defines the signature roll. The Infatuation describes that roll as roughly the size of a fancy dinner plate, with a dark-brown underside and an olive oil frosting that oozes from each layer. The Big OREO Roll takes that base and adds OREO cookie character throughout, then finishes with Oreo cookie chunks on top for texture contrast.
Loser’s Eating House’s signature sourdough cinnamon roll costs $19.99, according to The Infatuation, and that review notes it can feed six people. The Big OREO Roll follows the same large-format idea, with pricing set onsite at First Taste 001 for this one-day drop. The OREO cookie flavor profile layers onto a dough format that already has a strong track record in one of NYC’s most competitive pastry markets.
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4. How To Get It: First Taste 001 Logistics
First Taste 001 runs Saturday, September 19, 2026, from 2:00 PM to 8:00 PM EDT at LilliStar, the rooftop of the Moxy Hotel, 353 Bedford Ave, Williamsburg, Brooklyn, NY 11211. The event runs rain or shine. Entry is restricted to guests 21 and older.
Tickets use tiered pricing, with limited tickets available at the door. Advance tickets are available now at posh.vip/e/first-taste. Food drops, including the Big Oreo Roll, are purchased separately onsite on a first-come, first-served basis. Quantity is limited, so arriving early gives you the best chance to try everything.
Every guest receives a First Taste 001 passport at check-in. Collecting a stamp at all three food drops earns a limited-edition New York Penn tote, customized onsite with patches inspired by the lineup and New York City. The three drops on the lineup are The Big OREO Roll from Loser’s Eating House x Oreo, a Chinese Sausage & Peppers Detroit-Style Pizza from Potluck Club x Ace’s Pizza, and a Banh Mi Empanada from Titi’s Empanadas x After Eden.
Every guest 21+ is welcomed on arrival with a choice of one of Hennessy’s Very Special Cocktails, including the Henny Rita, Henny Berry, or Henny Iced Tea. The DJ lineup is built entirely around unreleased music. Sunny Cheeba goes back-to-back with Curly Nez, Just Dimy and Rae Sada bring new drops, and Dos Flakos premieres tracks ahead of their October release. New York Penn will debut a customizable jacket available only at First Taste 001, in three different colorways and personalized onsite.
Grab your ticket before the drops sell out
5. Frequently Asked Questions
Is The Big OREO Roll available anywhere other than First Taste 001 on September 19, 2026?
The Big Oreo Roll appears only at First Taste 001 on September 19, 2026. It was created specifically for this event as a collaboration between Loser’s Eating House and OREO brand. The drop is limited in quantity and tied to this single date and location.
What exactly is in the Big Oreo Roll?
The Big OREO Roll is built on Loser’s Eating House’s sourdough brioche dough, layered with butter made with OREO cookies, finished with the restaurant’s olive oil cream icing, and topped with OREO cookie chunks. It delivers an Oreo-cookie forward interpretation of Loser’s Eating House’s signature cinnamon roll format.
How much does a First Taste 001 ticket cost, and what does it include?
Tickets use tiered pricing, with limited tickets available at the door. Admission includes entry to the event, a welcome cocktail from Hennessy’s Very Special Cocktails lineup for guests 21+, a First Taste 001 passport, and access to the DJ sets. Guests then have the opportunity to purchase food drops onsite, including The Loser’s Big Oreo Roll. The event is 21+ only.
How does the Big OREO Roll compare to Loser’s Eating House’s regular cinnamon roll?
The signature cinnamon roll from Loser’s Eating House uses a sourdough brioche base and olive oil frosting format that The Infatuation highlights for its caramel-tasting dark underside and oozing glaze. The Big OREO Roll uses that same dough and frosting approach, then adds an OREO cookie flavor profile and Oreo cookie chunks on top for a different finish.
Is there a risk the Big OREO Roll will sell out before I get to it?
The drop is limited in quantity and available on a first-come, first-served basis. Arriving early in the 2:00–5:00 PM window gives you the strongest chance to secure the Loser’s Big OREO Roll and the other drops.
8it surfaces drops like the Loser’s Big OREO Roll in real time, before they sell out and before everyone else is talking about them. The app tracks limited-quantity pop-ups, one-day collaborations, and exclusive food events across NYC, so the 8it Fam always knows what is worth showing up for. First Taste 001 brings that idea into a single afternoon on one rooftop with three drops that exist nowhere else.
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