Chubba Whubba Bakery: Two Best Friends Bring Stuffed Cookies to the Hamptons 

Chubba Whubba Bakery has been winning hearts in the Hamptons with their unique stuffed cookies, which they call “Chubbas.”

Founded by best friends Elise Tomashoff and Debra Dalessio, “the baking grannies” who are often mistaken for sisters because they do everything together, operate the bakery right out of their kitchen.

“We have been best friends for a zillion years,” Elise said. “Owning a business with your best friend is great because we can literally finish each other’s sentences, and when we get mad at each other, we still have to talk to each other.”

The cookie journey began during the COVID-19 pandemic when Debra stumbled across a recipe and started experimenting with different kinds of stuffed cookies.

“I would hand them out, and Elise would say, ‘These are great, why aren’t we selling these cookies?’” Debra recalls.

After nine months of persuasion, Elise convinced Debra to turn their pastime into a business venture.

Chubba Whubba Bakery carries on the legacy of Elise’s daughter, Chelsy, who died 10 years ago.

“The inspiration for Chubba Whubbas was my daughter Chelsy. When she was a baby, I nicknamed her ‘Chubba Whubba’ because of her cute little belly,” Elise explained.

Chelsy’s life and love for baking are honored in every batch of cookies. The packaging is even pink because it was Chelsy’s favorite color. Debra, who was Chelsy’s Aunt Debbie, would always take Chelsy out for sweets.

“It is something I know Chelsy would have been so proud of. She would have been so happy because she would have been a part of it too with Debbie and me, I am sure,” Elise says.

The duo makes the dough, packages the cookies, and delivers the final products all on their own.

“We do it all,” Debra said. “And we are not so young either,” Elise added with a laugh.

They offer 14 different flavors of stuffed cookies, including Oreo, peanut butter cups, s’mores, chocolate marshmallow and dark chocolate sea salt. They recently added a new funfetti cookie called the Chubba Fetti and have plans to add a cookie with a brownie in the middle and M&M’s on the outside.

“The cookies are unreal,” Elise said. “They are soft and very big. I put a lot of stuffing in the middle,” Debra added.

A big surprise is coming soon, with the only hint being that it is green and white.

Chubba Whubba Bakery also customizes cookies for weddings, engagement parties, bridal showers and birthday parties. In the future they hope to expand into a commercial space so they can bake more cookies and ship them nationwide.

As Elise and Debra continue their sweet journey, one thing remains certain: “The Chubbas are made with love,” and that love shines through in every bite.

To place an order, customers can simply send a direct message or email to chubbawhubbabakery@gmail.com.

-PARTNER CONTENT