The Chronicle’s Business of the Month: Chilly Philly is keeping the Twin City cool

The Chronicle’s Business of the Month: Chilly Philly is keeping the Twin City cool
August 18
13:55 2021

By Busta Brown

The name sounds contradictive, but it tastes absolutely delicious. Philadelphians call it “Water Ice.” 

“Anywhere you go in Philadelphia, all they serve is Water Ice. It’s a summertime treat. When I was a child, no matter what park you went to, or what youth sports event you attended, day or night, there were Water Ice and soft pretzels everywhere,” said Wendy Robinson. She’s an administrative assistant in student services at Mt. Tabor High School in Winston-Salem. Wendy’s husband Frank Robinson is a pastor of Messiah Community Christian Church in Winston-Salem. 

One day Wendy called her good friend and church member, Andrea Main, with a business idea. “Thanks to COVID, we couldn’t travel home for about 16 months, and the first day in spring is always a big deal with Water Ice. So, my family and friends kept posting pictures saying it’s Water Ice time, and I got really homesick. 

“So, God laid it on my heart to call Andrea. I said we should open up a Water Ice store. And her comments were two words: ‘Let’s go!’ She didn’t ask me what kind of business. She replied, ‘Is it that stuff we had on vacation in Philly?’ I laughed and said yes, and she said ‘I’m in,’” shared Wendy. 

Her husband smiled at his wife with an expression of love and adoration and then joined in on the conversation. “Most people know it as Italian Ice, but if you know anything about Philadelphians, we always want to put our name on everything. So, we call it Philadelphia Original Water Ice,” joked Pastor Frank Robinson. He’s a USAF veteran and pastor of Messiah Community Christian Church. Frank and Wendy are the proud parents of two children and in October of this year, they will celebrate their 25th wedding anniversary. 

The Robinsons moved to Winston-Salem 11 years ago because of his ministry. Shortly after becoming a member of Messiah Community Christian Church, it wasn’t long before Andrea and Wendy became the best of friends. So, when Wendy shared her vision about starting a business together, she was all in. 

As of April 2021, Andrea, Wendy and Pastor Robinson are the proud owners of the hottest spot to cool off – Chilly Philly! “No business plan, just by faith. Like Andrea, let’s go!” said the Robinsons. 

“Busta, how the name Chilly Philly came about, we had several names, so we did a survey with our family members, and they voted. The name Chilly Philly stuck and that’s what we went with,” said Andrea Main. 

Andra, mother and the JROTC supervisor in the Forsyth County school district, is from Columbia, South Carolina. “I made my way here by way of the military,” she said. 

I asked, what’s the difference between Philadelphia Original Water Ice and shaved ice or snow cones?  “Italian Ice is served hard; Water Ice is served soft. It’s not served at a freezing temperature, which gives it that nice smooth texture. It’s fat free, no dairy, cholesterol free, soy free, gluten free, and produced in a peanut free plant. So, a lot of parents bring their kids in that have peanut allergies. We’re affordable. A family of five can buy Water Ice for their whole family with 20 dollars and leave with some change,” shared Wendy. 

Chilly Philly has plenty of flavors to choose from; banana pudding flavored Water Ice is my favorite. 

“One lady stopped making banana pudding after trying our banana pudding flavored Water Ice. We have about 40 flavors, but we rotate a different 12 flavors a day. We don’t keep the same 12 flavors and the people love it. The reason for the 12 flavors is because there are 12 letters in the name Philadelphia. And by the way, we do serve ice cream as well.” 

One of the customer favorites is the Philly Sampler. The Philadelphia Sampler is all 12 scoops in a large cup. Customers can sample up to two flavors and can choose two to four flavors in their cup. “Sometimes it’s hard for them to choose” said Andrea. 

When you stop by Chilly Philly, here are a few specials you’ll find: Sundaes on Sunday, which is 2&2 and add cake; milkshakes made from scooped ice cream; Chilly Philly 1&1, which is one scoop of ice cream with one scoop of Water Ice; and Chilly Philly 2&2, two scoops of ice cream and two scoops of Water Ice. 

Chilly Philly is very active in the Winston-Salem community. “When we first started our business, we said we want to be a blessing to young people by teaching excellent customer service, how to manage their money, and become entrepreneurs as well. We did a back-to-school drive for the teachers. Andrea and I both work for the school district, and we see our teachers taking money out of their pocket when kids don’t have [supplies]. The drive was very well received by the community. “We’ll also begin doing fundraisers this fall,” shared Wendy. 

I asked Andrea to share what’s in the future for Chilly Philly. “Well Busta, we have to keep you all guessing. It’s going to be pleasing, delightful, refreshing, and something to get our customers and community through the winter.” 

Pastor Robinson closed by assuring us that Chilly Philly is the real deal. “My brothers and sisters from Philadelphia were the first ones to come in to see if we’re the real deal, and when they tasted our Water Ice, they immediately said this is the real deal. We brought the spirit from Philly to Winston-Salem. Our ice cream is from Hershey Philadelphia, and it’s no taste like it. We specialize in Water Ice, but we serve the best ice cream as well.”

Chilly Philly is located at 454 Knollwood St. in Winston-Salem. Their summer hours are Wednesday – Saturday from 12 – 8 p.m. and on Sundays 2-8 p.m. For more info call 336-608-4068 or visit or on Facebook @chillyphilly.

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