Taking over a business requires a presence of mind and a sense of what came before while adding personal touches. Donavan Kennedy, who took ownership of Hillside Gardens in Colorado Springs in 2021, understood the need to keep the venue both classic (as it has been for many years as a wedding location) while implementing new ideas such as a possible whiskey bar.
“My sister Ashlee and I are both dreamers and have always been the type of people that see potential.” Hillside for Kennedy has always been the perfect place. Former owner Gary Gertsema had already made many improvements to landscaping and structure over nearly 25 years. Kennedy has ideas too, but with wedding season in full bloom through the summer, some of those will wait until the off-season.
Donavan is a Wine & Spirit Education Trust (WSET) Level 3 Sommelier and got to know Gertsema selling wine to the property for nearly seven years. Even in his off time, Kennedy used to come over and pour wine at the Summer Concerts at Hillside. It was a calming presence for him.
People had been pursuing Gertsema to sell the property for years because of its great location (4 acres just outside of town). Kennedy and his sister represented the kind of family-oriented approach with a focus on creativity and inclusivity that Gertsema wanted to pass on his legacy to.
Beautiful and Peaceful with a Ton of Flowers at Hillside Gardens
“So, the nice thing about Hillside is [that] it’s a beautiful garden with tons of flowers. When you walk in, you start to see how peaceful and beautiful everything is,” Kennedy says. “And the more you walk into the property, it really takes on its own oasis [feeling].”
Kennedy sees Hillside as a perfect spot for the celebration of life. “You can just hear the birds and you’ve got this sense of tranquility.”
Kennedy also likes its possibility because the property, at times, can be a blank slate. They can do whatever they want in the pavilion, and the gardens are already prepped with plantings. “People come here because they don’t have to do too much decorating because it’s an outdoor garden, but they can really make it their own. Like this past Sunday. there was [a party with] cowboy hats and cowboy boots, but then Saturday for a wedding, it was more black tie, so you can do anything here.”
Cactus Jacks is their tequila bar on site. Kennedy wants to take some more open specific corners on the property and give them their own identity with their own branding and intention like Jack’s. He is planning to implement a beer festival (or venture as he calls it) this summer. “We didn’t want to just do something that’s just standard. We really want to be able to have the freedom to be creative and not just something that is in every city or every strip mall.”
Perfect Timing and the Power of New Initiatives
The timing when Kennedy came to own the property in 2021 was perfect too because even with the COVID shutdown, the property itself could still do events such as outdoor dining. Adding to that is the fact that they are seasonal. “We shut down in the fall, in November, and open back up the following year [in the spring].”
With his wine and spirits background, Kennedy will also be able to bring more of that expertise to new initiatives. One of his mentors: Michael “Bucky” Buckelew (who was the Head Sommelier at The Broadmoor for many years) taught Kennedy a lot of what he knows about wine. “Bucky now is pouring wine every Wednesday at the wine bar,” Kennedy says that they are also planning to build a whiskey section/bar at Hillside that’s likely going to launch in late fall 2022.
To create the actual whiskey bar itself, Kennedy shares that one of their friends is a welder who is going to translate a unique piece of scrap metal they have into the actual bar. It will be another space, Kennedy explains, for people to enjoy themselves allowing for specialized events, parties, and whiskey tastings. The space, in and of itself, was an old blacksmith shop that Gertsema had on the property.
“It has this really fun ‘out west’ feel and I think it’s going to be a really fun project.” Once these new elements are implemented, Kennedy hopes they will be able to rent those spaces out for different events and not just for weddings.
Making Memories Humbly
Hillside Gardens for Kennedy is also about creating memories because that is what it did for him. He is always humbled by people’s reactions to the property. When he gives a tour to a possible new client and they pull into the parking lot, he says many don’t know what to expect. “And then it’s that moment where we start to walk down the pathway and they see that view of the mountains surrounded by the flowers. It’s just really satisfying to just get that sense of tranquility and awe.”
Kennedy says that they just recently had Gertsema’s retirement party where many of his friends who have been coming to Hillside for 25 years came to honor him. “Just seeing their reactions and hearing them talk about all the updates that we’ve done, meant a lot. And to have that kind of seal of approval from Gary, his friends, and his family… It was kind of like passing the baton. And it was just really special.”
But moving forward at Hillside is about both maintaining legacy but also updating in subtle but effective ways. “With the growth of our city, we need our landmarks. We need our spaces that have been here for more than a decade. And I think the growth of downtown has been so outstanding in my eyes. The quality is just going up, and the Springs has really become a place that has so much to offer.”
One of his clients from his sommelier days: (Paravicini’s Italian Bistro) mentioned something years ago that still sticks in his mind. “Restaurants die if they don’t get updated. If you don’t update after a certain amount of time, you start to just fall to the side.” Kennedy and his sister won’t let that happen at their new oasis. “We want to keep Hillside in motion, keep it ever-changing, take feedback, and keep making things better.”
