At Nathan Wright Landscape Design, we believe that outdoor spaces—no matter the size—can be crafted into something meaningful, beautiful, and ecologically vibrant. Our Director of Design, Hayden Regina, brings this philosophy to life in every project he leads.
One of Hayden’s most personal and celebrated projects is his own rooftop garden in Chicago. His design, featured in Fine Gardening Magazine and showcased on the cover of Tiny and Wild: Build a Small-Scale Meadow Anywhere by Graham Laird Gardner, transformed a 611-square-foot space into a functional gathering place for people and a thriving habitat for pollinators.
From Rooftop Deck to Rooftop Garden
When Hayden first moved into his condo, the rooftop deck was little more than rotting wood. Instead of seeing a limitation, he saw potential. The redesign became an opportunity to create an outdoor living space with a larger ecological agenda in mind.
Hayden approached the project with two goals: to create a highly functional rooftop for entertaining—maximizing seating and circulation—and to design a habitat that would support biodiversity in the heart of the city. By minimizing hardscape and maximizing planting areas, he shaped two distinct gathering areas linked by a catwalk, with pollinator-friendly gardens filling the space between.
The result is a rooftop that works equally well for gatherings and for nature—where bees, birds, and butterflies have as much claim to the space as the people who enjoy it.
A Plant Palette with Purpose
Every plant was chosen with intention. Rather than focusing solely on aesthetics—or limiting himself to a strict native palette—Hayden selected “model citizen” plants: durable perennials and grasses that thrive in a rooftop environment while supporting pollinators throughout the seasons.
Coneflowers, penstemon, calamint, and grasses create a prairie-like matrix that thrives in shallow soil and withstands rooftop challenges. Birch trees add height, while subtle hardscape choices in muted tones keep the focus on the planting. The result is a wild yet refined garden—plants that perform, pollinators that flourish, and a landscape that balances resilience and ecological function.
Bringing Thoughtful Design to Every Project
What makes this rooftop remarkable is how it reimagines what a small urban space can do. At just over 600 square feet, it proves you don’t need acres of land to create a meaningful landscape.
Small-scale projects like rooftops and courtyards can have an outsized impact when designed with intention—supporting pollinators, enriching daily life, and reimagining what’s possible in the city.
Hayden’s rooftop garden may be personal, but the philosophy behind it informs all of his work at Nathan Wright Landscape Design. Whether crafting a modern backyard, an intimate city courtyard, or another rooftop retreat, Hayden designs with the belief that landscapes should be beautiful, functional, and ecologically rich.
See the full feature on Hayden’s rooftop garden in Fine Gardening
