Words and Photos by Gianluca D’Elia

Gail and Graham Cresswell have a classic Rochester love story. The couple met at Tiny’s Bengel Inn in Summerville, reconnected while working together at the Eastman Kodak Company, went on date nights at Schaller’s Drive-In multiple days a week, and started their life together in a small Dewey Avenue apartment before raising their family in Greece.

Now, you can add Grandma Gail’s Ice Cream Shoppe to the list of significant Rochester landmarks that have shaped the Cresswells’ 58-year marriage. 

Tucked under a towering billboard in the corner of a shopping plaza parking lot at East Main Street and Winton Road, North Winton Village’s newest dessert spot boasts classic flavors, cookie sandwiches, and even “ice cream flight” sundaes with three flavors for those who don’t want to limit themselves to one. There’s even a signature menu item, the “McBlizzy” — a blended treat that’s a little bit thicker than a milkshake, with candies blended in. 

The small, periwinkle blue shack is the ideal spot for an after-dinner ice cream trip, complete with a picnic area and adirondack chairs that are perfect for taking in the sunset, and an enthusiastic, friendly team behind the counter who make it a point to say, “my pleasure” when a customer thanks them. 

Gail and Graham’s grandson, Rochester-based real estate owner and remodeling contractor Josh Cresswell, started the ice cream stand as a passion project with money he’d made from flipping properties.

“I live right there, but I used to drive all the way to Webster for ice cream,” he said. “The building was vacant for a while. I’d always drive by and say, ‘that would be such a good ice cream place.’ Eventually, I decided I should stop talking about it and just do it.”

Gail enjoys a good ice cream sundae now and then, but it was Josh’s idea to name the shop after her. He wanted it to make it a go-to, family-oriented spot with a “classic, hometown feel” for residents of the neighborhood.

Before telling the name origin story, Gail and Graham beam about their children and grandchildren over a Zoom interview, giving a brief synopsis of what each of their grandchildren are up to.

“We’re very proud of Josh,” Gail said, recalling that she was taken by surprise when Josh told her he’d bought a small property and wanted to turn it into an ice cream shop with her name on it. “I walked around smiling for the next month or so.”

On a stretch of the neighborhood that’s home to several popular restaurants and bars like JJ’s Pub, the Silver Iguana and Lucky’s, an ice cream shop with an all-ages appeal is a welcome addition to the row of booming local businesses. 

“My grandparents used to tell me about going to Schaller’s when there were car shows, dancing and 25-cent ice cream,” Josh said. “A lot of places like that don’t get frequented anymore, and a lot have been replaced by more high-end places.”

The Cresswells said they’re passionate about building a sense of community through their business. 

Quickly after Josh announced the new shop, the shop’s employee roster was quickly filled by local high school and college students looking for work over their summer vacation—most of them also live around the North Winton Village. As Joshua recalls, “I was able to hire 8 people in a matter of two hours.” 

Within a month of opening, the shop built up a steady base of regular customers and continues to pick up more traffic. And it hasn’t shown signs of slowing down as the seasons change. The Grandma Gail’s crew has even introduced fall flavors like pumpkin and apple pie. 

“This area is surrounded by small businesses, locally owned restaurants, and residents who have been here since they were kids,” Josh said. “We want to be here for a long time.” 

And who knows? Maybe Grandma Gail’s will even be that date night spot in someone else’s 58-year marriage.  

Grandma Gail’s is open on weekdays from 5:30 to 9 p.m., and weekends from 12 to 9 p.m. Discounts are available for members of the military, first-responders, health-care workers.