Windermere Wine & Dine under new leadership

In the 11 years of helping to organize the annual Windermere Wine & Dine, CT Allen had not eaten at the event, as she always was running around to make sure everything was operating smoothly.

But at the 2025 Windermere Wine & Dine in January, Allen allowed herself to take the time to sample some of the restaurants at the event. She thought it could be the last year of the Windermere tradition as she and the other six community volunteers who have organized the event since its inception had spent six months looking for the perfect group or organization to take over the event with no luck. They were considering closing up shop. 

Luckily, Allen connected with Stephen Lewis, the president and CEO of the West Orange Chamber of Commerce, and learned of the chamber’s West Orange Foundation. The foundation is the philanthropic arm of the chamber. 

“If it wasn’t for Stephen at the helm, we probably wouldn’t have done it only because we wanted to make sure the mission stayed on point with what we had established,” Allen said. “We just didn’t want to give it to any business or any entity that was just in it for the dollars. It was the whole community based esthetics of it; it was built on the community. The community helps with it. We wanted all of that to be part of the package.”

Knowing the West Orange Foundation had a broader community reach and would maintain Windermere Wine & Dine’s mission and quality, the seven leaders of the event agreed to hand over their “baby” to Lewis and the West Orange Foundation. 

Windermere Wine & Dine has transcended from a grassroots fundraiser to an event that draws more than 1,000 people with tickets selling out within minutes and raising hundreds of thousands of dollars. 

A group of seven parents with children at Windermere Elementary School came together in 2008 when there were budget cuts. The group wanted to raise money to provide technology to the school, so the parents created the Mustang Education Fund. 

By the third year, the group realized it needed another revenue source. Thus, Windermere Wine & Dine was created. 

The first Windermere Wine & Dine had 13 restaurants, which the core seven had to go door-to-door to obtain. The event raised $35,000. 

“Obviously, we thought it was one-and-done, and it never came a one-and-done,” Allen said.

The 2025 Windermere Wine & Dine resulted in more than $200,000 being given to local charities. 

Allen said the group always knew it could do more, but the members just didn’t have the reach to make it happen in the way they wanted. 

Lewis said the foundation has been looking for a sustainable additional revenue source to support the foundation and its mission to give back to the community. 

“We batted around some ideas, but nothing that was going to generate that kind of revenue,” he said. “So in hearing this was an opportunity, and then talking to CT and hearing how much it’s generated, how much it’s given back to the community, we saw our models were aligned. … We always try to give back to the community in some way but smaller compared to what wine and dine had been able to do. It was just a perfect fit for us.”

Maintain the mission

Although the West Orange Foundation will be running Windermere Wine & Dine, Lewis assured the quality of the event will not be diminished under new leadership. 

“I live in the community just like CT and all the original seven,” Lewis said. “For me, that’s important. Not only do I live in the community, but with the chamber side of things, I work in the community, too. I want it to be a high-end, elevated event that continues the legacy that’s been created.”

The featured charity for next year’s event is Get Cooking, a nonprofit with award-winning chefs who teach families in need how to cook healthy dinners for under $20. The nonprofit will have an opportunity to showcase what they do at the event.

Tickets for the 2026 Windermere Wine & Dine go on sale Saturday, Oct. 25. Lewis said sponsorships already are sold out and there are 34 restaurants already contracted to participate with a wait list. 

“We’re still sticking with the traditions, making sure that the community is the first to know about the event,” Lewis said. “The community supported it for 11 years, and we want to continue that.”

Lewis will go to Allen’s house Saturday, Oct. 25 to watch the approximately 700 tickets available be sold. 

“I usually have a bottle of champagne, and we’ll watch it and then he gets to have the joy we have every year that it’s sold out,” Allen said. 

Allen said they created the Windermere Legacy Fund two years ago and saved seed money to be able to continue to donate to local charities if the Windermere Wine & Dine no longer would be held. As part of the contract with the West Orange Foundation, it was agreed that 75% of the proceeds from wine and dine will go to the foundation but the other 25% will go to the Windermere Legacy Fund. 

She said the Windermere Legacy Fund is going to help residents fund charitable initiatives they have and find important by applying for grants through the fund. 

“We wanted to make sure (residents) understood that dollars will still remain in Windermere, and it’s all about engagement with the residents,” Allen said. “It’s to get the residents more involved in charitable endeavors. … We want our residents to start engaging in giving outside of our borders.”

Allen said there are Windermere residents who want to volunteer, donate and support local charities, but they don’t know where to start. The Windermere Legacy Fund can help connect residents to verified and vetted charitable causes. 

She said the details of the Windermere Legacy Fund still are in the works, but she can foresee giving out $50,000 each year to support charitable efforts.