Gas pumps and a classic red 1966 Ford Mustang greet customers outside Redd’s Filling Station in downtown Windsor.
Inside the retro-style restaurant is a 1950s jukebox, vintage Coke machine and other nostalgic collectibles to take you back in time. The Isle of Wight County landmark also features a mini golf course, cornhole, table tennis, foosball, a Tiki-style bar and an outdoor stage for live entertainment, including local bands.
Jake Redd opened the restaurant in the restored 1950s gas station in August, selling his favorite go-to meal since childhood: chicken with a wide array of sauces. The menu features a variety of made-from-scratch Southern comfort food.
Redd’s grandparents, Cecil and Barbara Dean Redd, had owned the building and operated Windsor Gardens, a landscaping and florist shop there. Throughout the years, the property housed numerous businesses, including a dog groomer, veterinarian and other restaurants.
The building was in need of TLC, and Redd was up to the challenge of extensive renovations. He was also eager to make his dream of business ownership — which seems to run in his blood — a reality.
“I had to figure out a plan to turn this old, raggedy building into a restaurant,” he said.
He shared his idea with his grandmother, who gave her blessing before she died in January. The Mustang is a reminder of her everlasting guidance and adoration — she gave him the car for his 16th birthday.
The surname Redd — and the accompanying red signage — is familiar to many in the small town.
Redd’s grandparents also operated Redd’s Supermarket in Windsor from the 1960s until they sold the business to IGA in 1992.
“They were somewhat innovative for their time,” Redd said. “They had a drive-thru deli and were one of the first stores in the area to sell Virginia lottery tickets.”
Four years ago, Redd also renovated that nearby commercial building, which remained owned by the family, and turned it into Redd’s Climate Controlled Self-Storage.
And Redd helps his girlfriend, Francesca Ciula, operate Fizz Fusion, a dirty soda and specialty coffee shop, from a bright pink mobile trailer in the parking lot. The shop, complete with a drive-thru, outdoor seating area and a swing, has become a popular spot for locals and travelers along U.S. 460 since it opened in 2024, Redd said.
“We sell close to 500 drinks each day on average,” he said.
Overall, Redd said it feels amazing to continue to create a sense of community in his hometown — like his late grandparents did.
Durwood Scott, a resident of Windsor for eight decades, knew Redd’s grandparents and great-grandparents.
“He’s got a real imagination and foresight of things, ”Scott said. “Sort of like his granddaddy; he could visualize things and make them happen.”
Sandra J. Pennecke, 757-652-5836, [email protected]