Over the Oreos? Bored with Belvita?
There’s a cookie on the Hamptons culinary scene that’s changing the local baked good game. And it’s a pretty big deal.
Chubba Whubba Bakery, founded by best friends Debra Dalessio and Elise Tomashoff, features large cookies uniquely stuffed with all sorts of goodies. Dubbed “Chubbas” by their creators, each cookie weighs in at about a half a pound and is stuffed with myriad confectionary toppings and ingredients, ranging from peanut butter cups and Nutella to dark chocolate chunks with sea salt and marshmallows.
“We spare nothing,” laughs Tomashoff.

During the pandemic, Dalessio, an Eastport resident, started experimenting with baking, exploring recipes for cookies that were stuffed with different ingredients, and ultimately using Tomashoff and her husband as her product testers. After handing them out to friends, Tomashoff noted how popular the cookies were and implored Dalessio to partner up and go into the cookie business together.
“When Covid ended, I kept after her,” Tomashoff says. “I thought ‘Why don’t we expand it, tweak it, make it our own and make it into a business?’ It was something that she and I could do together. We are BFFs, after all.”
So, that’s what they did. Officially launching the bakery about two years ago and naming it in honor of Tomashoff’s daughter, Chelsy, an avid baker in her own right who died about a decade ago. “Chubba Whubba was a nickname I had for her when she was a baby,” Tomashoff says, “because she had this cute little, chubby tummy.”
In addition to carrying on Chelsy’s legacy the name totally fits the bill as a physical descriptor, with each Chubba weighing in at about a half a pound and having at least a 6-inch diameter. Presently, the cookies are baked out of Tomashoff’s home in Westhampton Beach, but the pair are looking to move their operation to a larger commercial space in Calverton in the next month or two, they say.

So far, thousands of cookies have been baked, packaged and sold since the bakery’s inception with shipments ranging as far as Florida, Pennsylvania and California. In addition to being available for purchase online (each cookie is $7), Dalessio and Tomashoff’s Chubbas can be found locally at several business throughout Easport, Center Moriches, and East Quogue as well as at the Westhampton Beach Farmers Market.
“We started delivering locally,” Tomashoff says, “and then it just expanded to more local places out in the Hamptons,” with future clients DMing and emailing for private Chubba orders for weddings, engagement parties, birthday parties and more.
With each cookie made from a basic, homemade chocolate chip cookie dough there are 14 flavors available. Flavors include Oreo, sea salt, s’mores, Nutella, peanut butter cup, marshmallow, Snickers, brownie, peanut butter chip and M&M. Most recently, the pair developed a sugar cookie Chubba stuffed with rainbow sprinkles instead of chocolate chips. A stuffed cheesecake Chubba is in the works.
To place an order, email [email protected] or send a DM through the bakery’s Instagram here.