When Is the Best Time to Plant?

When to plant... that is the question. And the good news is: you can plant just about anytime.

Here in Chesapeake, we have a fairly long planting season. There isn't one tiny window where a new perennial garden has to be installed. Instead, each season has its own advantages and considerations.

If we had to rank our favorite times to install a new perennial garden, it would look like this:

1. Fall

2. Spring

3. Winter

4. Summer

But that doesn't mean you need to wait for the "perfect" season to get started.

Fall: Our Favorite Time to Plant

For most perennial gardens in Southeast Virginia, fall is the sweet spot.

September through November brings gradually cooler air temperatures while the soil remains warm enough for roots to continue growing. Instead of putting all of its energy into surviving heat and producing new top growth, a plant can begin quietly establishing its root system.

That gives your garden a major advantage when spring arrives.

Plants that go into the ground in fall often emerge the following year already partially established, allowing them to put more energy into new growth and flowering rather than spending the first part of the season recovering from transplanting.

Fall planting also typically means:

• Less heat stress
• Slower moisture loss from the soil
• Fewer extreme watering demands
• More time for roots to establish before summer
• A stronger start the following spring

For larger perennial gardens, native plantings, shrubs, and trees, October and November can be some of the best planting months of the entire year in southeastern Virginia.

Spring: A Very Close Second

Spring is another excellent time to plant.

March through May offers cooler temperatures, regular rainfall, and a long growing season ahead. It is an especially good time to install gardens if you want to watch them begin filling in that same year.

Plants installed in March or April have several months to establish before our hottest weather arrives, which gives them a strong head start.

As we move toward late May and June, watering becomes increasingly important as temperatures begin to rise. The plants can still establish beautifully, they just need a little more attention as summer approaches.

Winter: An Underrated Planting Season

Winter often gets overlooked, but in Hampton Roads, it can be a surprisingly good time to plant.

Our winters are generally mild enough that the ground remains workable for much of the season. During this time, plants are dormant or growing very slowly above ground, which means they aren't dealing with the same demands from heat, flowering, or rapid top growth.

As long as the soil isn't frozen, waterlogged, or otherwise unworkable, many hardy perennials, shrubs, and trees can be planted successfully during winter.

You may not get the instant visual impact of a spring or summer installation, but that's okay. A winter-planted garden is essentially getting settled in before the big show begins.

Once temperatures warm in spring, those plants are already in the ground and ready to take off.

Summer: Absolutely Possible, Just Thirstier

Yes, you can plant in summer too.

Summer planting sometimes gets a bad reputation, but it isn't inherently a bad time to install a garden. The biggest difference is simply that newly installed plants need more consistent watering.

A new perennial doesn't yet have the extensive root system of an established plant. During our hot Hampton Roads summers, especially during stretches in the 90s, plants can lose moisture quickly.

That means a summer installation may require more frequent monitoring and watering during the first several weeks.

There are also some advantages to summer planting. Plants are actively growing, gardens are easier to visualize in their full form, and many perennials are blooming, making it easier to see how colors, textures, and mature plant combinations will work together.

With the right watering plan, proper soil preparation, mulch, and plants suited to the conditions, a summer-installed garden can still establish beautifully.

The key isn't avoiding summer — it's understanding that summer plants need a little more help while they settle in.

So, When Should You Start a New Perennial Garden?

Whenever you're ready.

If you have complete flexibility, we generally prefer:

Fall first, spring second, winter third, and summer fourth.

But we wouldn't tell someone to wait months to create a garden simply because it isn't the "perfect" planting season.

Timing is only one piece of a successful planting.

Sun exposure, drainage, soil conditions, available space, mature plant size, moisture, plant selection, and proper watering can matter just as much, and often more, than the month the plants go into the ground.

A well-designed garden considers all of those factors before the first hole is ever dug.

And when plants are selected intentionally, placed where they can thrive, and cared for properly while they establish, there's no reason you can't start creating the garden you've been dreaming about now.