Urban on Plant Kitchen & Bar is under new ownership

Holt Cappleman took a break from his decades-long career in the restaurant industry in the mid 2000s to try working in the insurance industry under his father, Larry Cappleman.

He was happy to be at home in Winter Garden with his family, but after two years, he was itching to get back into the restaurant industry and craving the creativity restaurants offer.

In July, Holt Cappleman had the opportunity to combine his passion for restaurants with his desire to be with his family in Winter Garden and work once again with Larry Cappleman. 

While working for the insurance agency, Holt Cappleman was able to see the business world through his dad’s eyes. Now the roles have reversed as Larry Cappleman, who has no experience in the restaurant industry, has taken ownership of Urban on Plant Kitchen & Bar in downtown Winter Garden with Holt Cappleman. 

The Capplemans took ownership of Urban on Plant Kitchen & Bar July 1. 

The Capplemans have served as the landlord of Urban on Plant since it moved to Winter Garden in 2012. 

When David Downs, the previous owner of the restaurant and bar, came to the Capplemans to tell them he was selling the business, the Capplemans felt the need to preserve the restaurant.

“We just thought this restaurant was too much of a staple of the community and too important to let it go to someone else who’s going to change the vision of it and turn it into something else,” Holt Cappleman said. 

Photo by Liz Ramos

The Capplemans are planning a gradual change of menu that still will have fan favorites such as the French dip and the black and bleu pizza. Holt Cappleman said they are gathering feedback from staff and clients about their favorites.

“We don’t want to ostracize people and take away things that everyone loves, but we would like to put our take on new items,” Holt Cappleman said. 

Urban on Plant will be launching a fall food menu in October with some additional items that will feature flavors of that season. From then on, the menu will become seasonal along with its classics that won’t change.

Holt Cappleman said the seasonal menu provides an opportunity to create an environment that allows guests to try something new every time they come into the restaurant. 

The drink menu also will be redeveloped. 

“In that space, we really want to allow our bartenders when they’re creating drinks to be overly creative and make stuff that people want to come in and take a photo of and put up on their Instagram or TikTok,” Holt Cappleman said. 

A focus for the Capplemans not only is preserving the legacy the restaurant has developed on Plant Street but also adding to the legacy of the Cappleman family on Plant Street. 

Urban on Plant is the fifth business the Cappleman family has owned on Plant Street since 1912. The family has owned a grocery store, an insurance agency and real estate and rental businesses. 

Holt Cappleman said preserving the family’s ability to have businesses and provide for the community is the family’s legacy, and now having the restaurant is a new aspect to add to the legacy. 

“Continuing that through giving them great service and providing food they’re happy to come and enjoy and a restaurant they’re proud to have in their community is really important to us,” he said. 

Urban on Plant was an opportunity for Holt and Larry Cappleman to go into business together for the first time. 

“I thought that was important for us to do, especially with the wonderful restaurant that David (Downs) and Jane (Thomas, the retired general manager) built together,” Holt Cappleman said. “To be able to continue the legacy they’ve created and expand on it is something we’re truly excited about.”

Holt Cappleman has more than 30 years in the restaurant industry and currently serves as the director of culinary operations and purchasing for Buca di Beppo and has been director of culinary operations for Bertucci, a pizza place, in the northeast. 

He also has worked with virtual dining brands to create brands such as Mr. Beast Burger and Pardon My Cheesesteak. 

“The controlled chaos is fun,” Holt Cappleman said. “I’m a pretty creative person when it comes to food, so I kind of thrive under that, as well.”

Holt Cappleman said teaching Larry Cappleman about the industry he’s known for 30 years is “really cool.”

“At my age, you’re not supposed to start something new, but it sure is energizing,” Larry Cappleman said. “We hope we’ll create a gathering spot for Winter Garden, a fun place where they can enjoy themselves.”

Larry Cappleman always enjoyed the interactions with the public in the insurance business, so he’s looking forward to doing the same at the restaurant, especially with regulars. 

Holt Cappleman said knowing Urban on Plant already has regulars provides pressure to maintain the legacy set ahead of them. 

“We don’t want to deviate too far from it,” he said. “We just want to expand on the experience they have when they come here and give them other opportunities to see things they might have not seen here before.