Hillside Gardens: Colorado Springs’ Secret Oasis
The story of Hillside Gardens stretches back more than a century. In the early 1900’s, long before it became a beloved event venue and concert destination, the four-acre property operated as a dairy farm. Years later, the space transformed into a charming neighborhood nursery, gradually earning a reputation for its eclectic beauty and whimsical atmosphere. Eventually, people began asking if they could host weddings and celebrations there, and Hillside slowly evolved into the magical gathering space locals know today.
In late 2021, brother-and-sister duo Donavan and Ashlee Kennedy took over ownership of the property, bringing fresh energy while preserving that same soul that made Hillside special in the first place. Both Colorado Springs natives with deep backgrounds in hospitality, wine, spirits, and community-building, the pair envisioned Hillside as more than just a venue. They wanted it to become a place where people connect, celebrate, relax, and experience the creative spirit of the city.
Which is exactly what they have done…
Walking through Hillside kind of feels like stepping into a secret garden curated by artists, musicians, and plant lovers. Everywhere you look there’s something unexpected: vintage décor, colorful flowers, eclectic sculptures, and retro bars, all surrounded by panoramic mountain views.
Throughout the summer, Hillside Gardens becomes one of the liveliest social hubs in Colorado Springs. The venue hosts weddings, private celebrations, garden events, food gatherings, and seasonal community happenings, but the crown jewel of the entire season is unquestionably their Wednesday Night Summer Concert Series.
Every Wednesday evening from May through early October, the gardens come alive with music, cocktails, food vendors, and hundreds of people gathering under the Colorado sunset. It’s become a summertime ritual for locals.
The format is simple but perfect: multiple live bands, local food vendors, craft cocktails, wine bars, lawn chairs scattered across the gardens, boasting an atmosphere that somehow feels both energetic and chill at the same time. Some people dance near the stage while others (like this blog writer) wander the grounds with drinks in hand, exploring the gardens as music echoes through the property.
What makes the Wednesday concerts so special isn’t just the music (although the lineup consistently highlights some of the best local talent in Colorado). It’s the setting. Hillside has managed to create an environment that feels like old school Colorado.
The community-first spirit is woven into everything Hillside does. The owners have intentionally cultivated a space where local musicians, food vendors, artists, and small businesses can thrive together. The result is an atmosphere that feels collaborative and not commercial, something increasingly rare and incredibly refreshing.
In a rapidly growing city, Hillside Gardens remains a reminder that the best places aren’t always the flashiest. Sometimes they’re the spaces built slowly, lovingly, and intentionally. One concert, one gathering, and one Colorado sunset at a time.