Fall Yard Prep in Chicagoland: What to Finish Before the Ground Freezes

October 5, 2026

Tommy Pollina Landscape Company handles fall yard prep in Chicagoland in four areas: lawn aeration and power raking, drainage and downspout checks, fall plantings and mulch, and hardscape repair. Finishing these before the ground freezes keeps water away from your foundation and gives your lawn, trees, and beds a head start on spring.

How do I know if my yard drains properly before winter?

Walk your yard during or right after a hard rain. Standing water, downspouts dumping beside the foundation, soil that slopes toward the house, and washed-out mulch all point to a drainage problem. Water that sits against a foundation going into winter freezes and expands there.

Fall is a good time to catch this because the ground is still workable. Once it freezes, we can't dig trenches or regrade, so a problem you spot in November often waits until spring.

Our drainage work follows one method. We take laser-guided measurements and set exact elevations. Then we intercept water at multiple collection points and carry it below grade to a controlled dispersal spot. Depending on the yard, that means French drains, channel drains, PVC drainage, downspout connections, swales, flow wells, or river rock systems. Our team holds NDS Professional Drainage Contractor certificates, and we've completed more than 10,000 drainage installations over 45 years.

Grading often belongs in the same conversation. If the ground itself slopes the wrong way, we regrade it and tie it into the drainage system so the two work together.

For an urgent situation, such as water moving toward the foundation right now, we run an emergency and expedited drainage service. We also design sump pump discharge solutions for wet yards. If your basement is already taking on water, we install interior and exterior basement waterproofing systems with a lifetime warranty.

Barbara Forrest wrote in a Google review: "We had a serious drainage problem in Bartlett that a severe storm made very apparent. We needed a good plan to resolve and experienced execution, and we got both with Tommy Polina. Before and after pictures tell the full story!!"

Lawn work: core aeration and power raking

Chicagoland lawns take a beating from summer heat, foot traffic, and compacted clay soil. We offer core aeration and power raking as two separate services, because they solve different problems.

• Core aeration pulls small plugs of soil out of the lawn so water, air, and fertilizer can reach the roots. It helps most on compacted ground.
• Power raking pulls up the layer of dead grass and debris sitting on top of the soil.

Our lawn maintenance program runs spring through fall. If we've been maintaining your lawn all season, fall aeration and raking fit into the same schedule. If you're starting fresh, we look at the lawn first and tell you which of the two it needs, or whether it needs both.

For lawns that need to be rebuilt, we install Kentucky Bluegrass sod as part of our landscape installation work.

Fall plantings, mulch, and seasonal color

Trees, shrubs, and evergreens settle in well when planted in fall, before winter sets in. Our landscape installation crews plant arborvitae privacy screens, Green Giants, Blue Arrow Junipers, Japanese Maples, hydrangeas, dogwoods, lilacs, ornamental grasses, and more. Every bed gets prepped with compost and fertilizer, then finished with mulch.

Mulch matters more than most people think. A fresh layer insulates roots and holds soil moisture. It also keeps beds looking tidy through the dormant months. We install it as its own service or as the last step of a planting job.

Fall also brings seasonal color. We plant fall containers and potted plants, and we build custom planters for entries, patios, and porches. Holiday container installations follow later in the season. Our gallery shows a winter container pot project we installed in Glenview.

If you're also trimming back overgrown trees or shrubs before winter, we handle tree trimming, pruning, tree removal, and stump grinding. We also do fall cleanup, so leaves and debris don't smother your beds and lawn.

Hardscape repairs to make before the freeze-thaw cycle

Water gets into the gaps of loose pavers, cracked bluestone, and failing retaining walls. Then it freezes, expands, and widens every gap. A small settled section in October can turn into a heaving, uneven patio by April.

Our hardscape team repairs and rebuilds brick and stone walkways, driveways, steps, patios, and retaining walls. We also install bluestone hardscapes and pave with asphalt and concrete. When a paver patio sinks, the cause is usually water or a weak base underneath. We fix that cause, because resetting the stones alone gives a short-lived result.

Which fall jobs should come first?

Start with water. Drainage and grading come first because they protect your foundation and need workable ground. Hardscape repairs come next, then lawn aeration and raking, then plantings, mulch, and containers.

Here's the order we suggest, and why:

Planning bigger projects over the winter

If you're thinking about a patio, outdoor kitchen, putting green, artificial turf, or a full backyard rebuild, fall is a good time to start the planning. Our landscape design service produces detailed 3D renderings and walkthroughs. The plans map grading, drainage, hardscape, and planting together, so the project can be priced, phased, or installed as engineered.

Emil of E1000 Music shared this in a Google review: "I hired Tommy Polina to landscape my yard before building a playground and to add rubber mulch after the playground was built. Marilee was great throughout the process and helped me scope the project reducing the area I had initially though while mantaining the safety."

You can browse everything we do on our landscaping and hardscaping services page. Joe Pollina started the company in 1982 as a one-truck operation on Chicago's Northwest Side, and you can read more about our team.

Frequently asked questions

Is fall a good time to plant trees and shrubs in Chicagoland?

Yes. Planting in fall gives roots time to settle before winter, and the soil is still workable. We plant arborvitae, evergreens, ornamental trees, flowering shrubs, and perennials in fall, with compost-prepared beds, fertilizer, and mulch. Tell us what you want and we'll plan the planting around your yard's conditions.

Do you offer fall cleanup?

Yes. Our fall cleanup clears leaves and debris from your lawn and beds. We can pair it with core aeration, power raking, mulch, and tree or bush trimming. Many clients bundle these into one visit so the yard goes into winter in good shape.

Can I start a design in fall and build in spring?

Yes. Our design process includes 3D renderings and walkthroughs, and the plan can be priced, phased, or installed as engineered. That lets you finalize the design over winter and schedule installation when the ground thaws. Drainage and grading work that needs unfrozen ground can often go in first.

Which areas do you serve?

We're based in Mt. Prospect and serve Chicago, the North Shore, and northwest suburbs, including Arlington Heights, Barrington, Buffalo Grove, Deer Park, and Deerfield. We take on residential and commercial projects across Chicagoland.

If you have a wet spot, a sinking patio, or a lawn that needs work before winter, tell us about it in the form below this article. We'll reply within 24 hours and help you decide which jobs to do first.