Our History
Hillside Gardens has a history as unique as this beloved venue. The beautiful four acres, with scenic mountain views, was used as a dairy farm in the early 1900s. Then, it became a neighborhood nursery in 2000. It was so charming that people started asking to get married there. Eventually, the whole place was transformed into the enchanting venue it is today.
At the end of 2021 brother/sister duo, Donavan and Ashlee took over ownership of Hillside Gardens. Like all old places, Hillside probably has a thousand stories to tell. We hope you join us to be a part of this new chapter.
Explore the Grounds
The Pavilion
Our largest covered event space, the Pavilion seats up to 150 guests. Surrounded by gardens and mountain views, it's the centerpiece for weddings, concerts, and private celebrations.
The Vintage Truck Bar
A fully functioning bar built into a beautifully restored vintage truck—quirky, photogenic, and always a hit with guests.
The Boneyard
An eclectic outdoor venue space with its own stage and the retro Trailer Bar, ideal for live music, private events, or just enjoying the vibe.
The Garden Center
Reopened in 2024, our revitalized Garden Center offers seasonal plants, veggies, herbs, and expert advice. Whether you’re a seasoned gardener or just getting started, it’s a welcoming place to dig in.
Local Artist Displays
All around Hillside, you’ll find sculptures, installations, and rotating artwork from talented local artists. [Link to Artist Bios]
Ceremony Site
Nestled under mature trees and blooming beds, this serene setting is the perfect backdrop for saying “I do.”
Cactus Jack’s Greenhouse & Tequila Bar
Part plant jungle, part tequila lounge—this space is both a lush escape and a fun gathering spot filled with greenery, cocktails, and good vibes.
Maggie’s: Gift + Wine Shop
Tucked beside the gardens, Maggie’s offers curated gifts, artisan goods, and a wine shop where you can sip while you browse.
Hillside Coffee
Our cozy coffee shop serves espresso, tea, and pastries with relaxed garden seating—open seasonally and perfect for a slow morning or afternoon pause.
Cactus Garden
A unique outdoor garden showcasing cacti and succulents hardy to the Colorado Front Range—a nod to resilience and creativity.
It’s Nice to Meet You!
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Donavan Kennedy
OWNER
Meet Donavan Kennedy, owner and manager of Hillside Gardens. As a Colorado Springs native, Donavan has enjoyed watching the city sprawl and mature over time. In years past, you may have run into Donavan at Yobel Market, which he co-founded in 2008. During his tenure there, he loved teaching small business owners all over the world how to build strong, sustainable businesses and helped fund school building projects in developing countries.
For the past six years, he has been selling wine and spirits to restaurants as a level 3 Sommelier WSET. Hillside concert-goers may recognize Donavan as the wine expert at the Wednesday Concerts over the past five years. With over 20 years of hospitality industry experience and a passion for his hometown, Donavan is excited to utilize Hillside as a place to connect, be refreshed and celebrate.
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Ashlee Kennedy
OWNER
Meet Ashlee Kennedy, owner of Hillside Gardens. Ashlee is a Colorado Springs native and a mountain girl, through and through. Though she always loves to come home, her adventurous spirit and her work in the non-profit sector has taken her all around the world. Those years of travel truly opened her eyes to the beauty of different cultures, food, and drinks. Most recently, as a WSET level 2 in Spirits, she has worked in the hospitality industry as a spirits and wine rep. Ashlee will bring her passion for food, wine, community and culture to create a welcoming and fun atmosphere at Hillside to share with Colorado Springs!
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Donna Ammann
GARDEN MANAGER
Meet Donna Ammann, manager of the garden center and grounds at Hillside Gardens. Born and raised in Maryland, Donna moved to Colorado Springs in 2014. After working in the restaurant industry for over 30 years she decided to make a career change and started working at a local garden center in town.
She spent her youth going to garden centers and working in the yard with her mom so when she decided to make the change, it felt like she was supposed to be doing it.
Over the past 6 years, Donna has immersed herself into the world of high desert gardening. Her love of birds, pollinators and native plants has made her a perfect addition to Hillside Gardens. You can find Donna on property almost every day, usually teaching new gardeners and out of state customers the challenges and rewards of gardening in Colorado.
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Erika Weeks
WEDDING COORDINATOR
Meet Erika Weeks, on-site wedding planner/coordinator at Hillside. She oversees all of our contracts and is available to help Hillside couples through full-service planning or coordinating services. She has been with Hillside since 2019 and loves the uniqueness every Hillside wedding brings to the gardens - she loves to see how each couple brings their own personal touches and the gardens transform to make a perfect space for the perfect day. Her greatest joy is helping couples be fully present in the moment while she oversees everything else.
When she is not at the gardens Erika is enjoying life raising her three little girls and going on date nights with her hubby of 10 years! Always ready to talk weddings, Erika is happy to sit down and talk about your vision over a decaf vanilla latte anytime!