Your yard doesn't need to be a showpiece—but when half the neighborhood's walking past your house on their way to the Yankee Doodle Fair or heading home from the farmers' market with armfuls of sunflowers, it's nice if it doesn't look like you've given up. Westport's packed with festivals, beach days, and weekend events, and your outdoor space is quietly part of that rhythm whether you're hosting or just keeping up.
Here's what actually happens around town, and how to make your property work with the season instead of against it.
The Local Calendar (and Why It Matters for Your Yard)
Memorial Day Weekend kicks off with the Westport Fine Arts Festival—two days of juried artists, families downtown, and the unofficial start of "people are outside now" season. A couple weeks later, the Yankee Doodle Fair takes over with rides and fried dough, and by then your spring plantings either look great or they don't. The Westport Farmers' Market runs every Thursday from May through November, which means there's a steady flow of fresh ideas (and fresh flowers) if you're the type to pick up a flat of annuals on impulse. And Sherwood Island State Park stays busy all summer—swimming, disc golf, dune walks—so if your property's anywhere near the coast, you're dealing with salt spray and sandy shoes.
The point isn't to landscape for these events. It's that your yard gets more foot traffic and more eyeballs during festival season, and a little intentional maintenance goes a long way.
Spring: Get Ahead Before Everyone's Outside
April and early May are your window to clean up beds, edge borders, and get irrigation checked before the Memorial Day crowd shows up. If you've got walkways or front-facing beds, plant hardy spring bulbs and early perennials now—they'll bloom right when people are actually paying attention. We've seen plenty of homeowners scramble in late May to make things presentable, but by then you're playing catch-up. Inspect your irrigation system early, too. A small leak in April turns into a brown patch by July, and nobody wants to hand-water all summer.
Summer: Flexible and Low-Maintenance
Once beach season hits, your outdoor space should work for you, not create extra weekend chores. Foldable seating, stackable chairs, or a simple gravel area gives you room for impromptu gatherings without a full patio remodel. If you're near the coast—and in Westport, that's a lot of properties—stick with salt-tolerant plants and coarse sand mixes in your beds. It's not about being fancy; it's about not replanting the same hydrangea three times because it can't handle the spray.
Containers are your friend here. Fill them with pollinator-friendly perennials, group them near your entry or patio, and you've got instant color without the commitment of a full bed redesign. Pathway lighting helps too—solar LEDs are cheap, easy, and they mean people aren't tripping over your steps after a farmers' market evening concert.
Fall: Extend the Season, Prep for Next Year
September and October are underrated planting months. Late-season shrubs and ornamental grasses go in now and look good through Thanksgiving. Your lawn mower needs a tune-up before you put it away, and dead wood should get pruned so your yard doesn't look abandoned during harvest fair season. Mulch your beds to hold moisture and protect young plantings—it's boring work, but it saves you from watering in late fall and keeps things tidy when neighbors are out walking.
This is also when you should plan any hardscape projects for next spring. Contractors book up fast once the weather turns, so if you've been thinking about a modest patio or a better drainage solution, start those conversations now.
Winter: Low-Effort, High-Impact Maintenance
Westport winters aren't brutal, but they're wet and unpredictable. Wrap young trees, move containers into a sheltered spot, and call it done. If you're itching to plan something, winter's the time to sketch out next year's entertaining area or figure out where a few native plant pockets might reduce your weekly maintenance load.
A Quick Checklist Before a Big Weekend
Mow, edge, clear debris. Sweep your paths. Group a few potted plants near the door and toss in some fresh blooms if you're feeling ambitious. Check your outdoor lights and replace dead bulbs. That's it. You're not staging a home tour—you're just making sure your property looks like someone lives there.
Westport's festivals and outdoor spaces don't demand perfection, but they do reward a little seasonal attention. If you'd like a quick, no-pressure visit to talk through a planting plan or a small entertaining area that fits your budget and schedule, we're happy to share what works in this climate. Just local know-how and practical ideas—no sales pitch required.
.svg){kind=small}
