A Year Of Fine Gardening

A Year in the Life of Rooftopia: Behind the Scenes with Our Fine Gardening Team

At Rooftopia, the changing seasons are more than a shift in weather—they mark a full-on symphony of planning, planting, pruning, and preparing. With over 120 fine gardening clients and new projects underway each month, we stay busy year-round making sure every container, rooftop, landscape and garden bed gets the care it deserves.

Here’s a peek behind the scenes at what our Fine Gardening and Seasonal Maintenance team is up to each month. Spoiler alert: it's a lot more than just planting flowers.

January: Kicking Off with Contracts

After a much-needed winter break, our account manager returns to one of the most important tasks of the year: preparing and sending out seasonal fine gardening contracts. These agreements cover everything from spring installations to winter décor and require careful estimation and coordination. We start selecting color palettes and planting designs while racing to meet the pre-book deadlines for spring plants—yes, even when it’s snowing outside.

February: Strategic Planning (and Coffee)

February is all about setting the stage. It may be sleepy and cold outside but our office is warm, caffeinated and buzzing with activity as we update internal policies, plan crew schedules, and post job openings for the upcoming season. Our designers and account manager finalize summer plant palettes while our field managers begin prepping for early spring deliveries. It’s the calm before the (colorful) storm, and we take full advantage of it.

March: Hiring, Training & Spring Prep

In March, hiring kicks into gear. We interview and onboard new team members and update training documents so everyone’s ready to hit the ground running. We also fine-tune our early spring orders, clean and sharpen tools, organize irrigation supplies, and stock our shop with everything we’ll need to welcome the first plants of the season.

April: Spring Has Sprung (Sort Of)

Spring containers begin to bloom, rain becomes a near-daily guest, and temperatures swing wildly. But we’re ready. Our teams install spring annuals, manage watering schedules, and coordinate closely with clients. This is the first major push of the year—and yes, it’s as intense as it sounds. We pack the rain gear daily and check weather apps on the hour, juggling whatever mother nature has to throw at us in order to get the work done. 

May: Summer Planting Begins

May is our official summer kickoff and one of our busiest months of the year. Once the frost-free date hits (hello, Mother’s Day), we begin installing planters filled with vibrant annuals and perennials, set up irrigation systems, and complete thorough spring clean-ups. Our fine gardening and installation crews work in sync to tackle gardens, decks, rooftops—everything clients want looking picture-perfect before Memorial Day. Behind the scenes our teams are accepting weekly deliveries of flowers, caring for our plant inventory, and labelling curated selections for each of our clients on a daily basis.

June: Peak Season, Full Bloom

June is also a busy time as summer planting is in full swing, and rooftops, decks, and gardens are buzzing with activity. It’s especially satisfying to see new installations come to life and to finally add the finishing touches—planters, lighting, and lush greenery—to projects that may have been built last season.

Our designers, account manager, and crew leaders stay in constant communication, adjusting schedules in real time to meet the demands of the season. And amid the planting chaos? We're already thinking ahead—pre-booking fall flowers, bulbs, and seasonal décor. Because yes, even in the heat of summer, we start planning our fall and winter containers!

July: Summer Projects & Rooftop Rush

With most summer plantings wrapped, we shift focus to our regular clean ups, weeding and pruning and larger landscaping projects. Our fine gardening team dives into tasks like power washing, pergola touch-ups, lighting adjustments, and making every rooftop and garden shine in time for the 4th of July. Because nothing says “summer in Chicago” like a rooftop deck with twinkling lights and cold drinks.

August: Gearing Up for Fall

We take a (very) brief breather, then dive headfirst into fall prep. Perennial installations, garden clean-ups, and ongoing maintenance continue, while behind the scenes, our account manager is finalizing fall planting orders and mapping out a packed schedule for the remainder of the year.

It’s also one of the best times to capture our projects at their peak—lush gardens, glowing planters, and that perfect golden-hour light. From sunset rooftop views to twinkle-lit patios, every space looks like it’s ready for its close-up.

September: Fall Arrives in Style

September is a team favorite. We’re wrapping up a few more new installations, larger landscape projects and looking forward to cooler temps, fresh fall palettes, and a new rhythm to the work. We begin fall planter installs, using cool weather loving ornamental kale, cabbages, grasses, peppers, pansies, and more to refresh outdoor spaces. The air gets crisper, and the gardens get cozier.

October: Fall Planting & Cozy Vibes

We’re in full-on autumn mode—think pumpkins, gourds, and rich earthy seasonal colors. Fall clean-ups begin, and we’re careful to protect pollinators and next year’s fireflies by leaving leaf cover in beds where appropriate. At the same time, we begin winterizing irrigation systems and tracking freezing temps. Timing is everything—we want to keep plants watered as long as possible while also winterizing all irrigation systems before persistent freezing temperatures settle in for the season.

November: Greens, Decor & Shutdowns

As winter creeps closer, we wrap up outdoor tasks: water lines are shut off, the shop gets cleaned and reorganized, and our first shipments of winter greens arrive. With the smell of pine and fir in the air we begin installing winter planters and festive décor while already thinking ahead to next year’s contracts. Yes, again.

December: Final Flourish & Winter Break

Our last big push of the year includes installing winter arrangements, sending out our client year-end surveys, and buttoning up the shop. Tools are cleaned, inventory checked, and our team heads into a well-earned winter break. As our gardens go dormant, so do we—for a little while, anyway.

In Closing…

Whether it's mid-July or mid-January, there’s always something happening behind the scenes at Rooftopia. Our fine gardening team works tirelessly to ensure every client’s outdoor space looks beautiful, healthy, and seasonally fresh.

So next time you see a perfectly planted container or a lush rooftop garden, know it didn’t happen by magic—it was carefully planned, coordinated, and executed with a whole lot of passion (and probably a few muddy boots).