Let’s set the scene. There’s late-summer light falling across a row of ginkgo trees, the quiet rhythm of brushes in rinse jars mixing with the hum of downtown Oak Park. A painter studies the curve of the Peterson’s Ice Cream sign, layering pinks and creams onto the canvas. Across town, another artist works in Austin Gardens, catching the last of the greens before the shade moves on.
From September 5 to 7, 2025, Oak Park is turning itself into an open-air art studio, and you’re invited to help make it happen. The first-ever Oak Park Plein Air Festival— hosted in partnership by Explore Oak Park and Beyond, the Oak Park Area Arts Council and the Oak Park Arts District — will bring artists from across the region to depict our streetscapes, gardens, parks, and architectural treasures in real time.
Whether you’re an artist with a portable easel or just someone who loves to stroll, linger, and watch a blank canvas come alive, this is a weekend that puts you right in the middle of the creative process.
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What’s “Plein Air,” Anyway?
If you’re new to the term, plein air (pronounced plen air) is French for “open air,” and it’s all about painting outdoors, on-site, capturing the immediate light, atmosphere, and movement of a scene. Think of it as the opposite of working from a photograph. It’s live, it’s fleeting, and it often comes with unpredictable changes in weather, light, and curious onlookers.
It’s also a tradition that goes back to the French Impressionists, who lugged their paints into the countryside to catch the play of light on water or the golden haze of a wheat field. In Oak Park, those scenes might be the warm brick and deep eaves of a Frank Lloyd Wright home or the wild blooms of Cheney Mansion’s gardens.
Where the Magic Happens
One of the joys of the Oak Park Plein Air Festival is that the “gallery” is the whole town. Over three days, artists will spread out to paint at some of Oak Park’s most beloved spots:
Frank Lloyd Wright Home and Studio – The birthplace of some of Wright’s most iconic ideas, this National Historic Landmark blends geometric lines, earthy tones, and intricate leaded glass.
Forest Avenue’s Wright-Designed Homes – Visiting this tree-lined stretch feels like stepping into an architectural timeline, where Prairie School masterpieces stand shoulder to shoulder. The leafy canopy and historic facades offer endless possibilities for capturing both detail and atmosphere.
Austin Gardens – Just off Lake Street, this pocket park is a painter’s oasis. Old oaks cast a shifting lace of shadows over winding paths, pollinator gardens buzz with life, and the air carries a calm that feels worlds away from the busy downtown nearby.
Downtown Oak Park District – Here, energy meets color. Street planters overflow with blooms, and vintage architecture frames storefronts. Artists can focus on a single corner or capture the whole lively rhythm in one scene.
Oak Park Arts District – The Oak Park Arts District is nestled in the tree canopy of Harrison Street. Be sure to stop by on Friday evening between 4-7 p.m. when all the local galleries and studios will be open and many local painters will be painting in the district.
Peterson’s Ice Cream Sign – A beacon of small-town nostalgia, this neon gem glows against the evening sky. The pastel curves and classic script offer a playful challenge to anyone wanting to mix architectural precision with a dash of whimsy.
Cheney Mansion – With its stately brick exterior and formal gardens, Cheney Mansion is like something from another century. Roses climb trellises and quiet nooks make it a dream setting for detailed, romantic work.
Pleasant Home – A National Historic Landmark and Arts and Crafts masterpiece, Pleasant Home is all soaring woodwork, intricate glass, and timeless lines. Its grand façade and architectural details provide endless inspiration, whether you’re sketching the ornate entry or capturing how afternoon light dances across the Prairie-style design.
The best part is you don’t need a ticket to enjoy the art in progress. Take a walk, strike up a conversation with an artist, and watch a blank surface slowly turn into a snapshot of Oak Park in late summer.
Click here to see the map of painting locations.
How the Festival Works
Sure, this is about painting, but it's also a full-on competition with seven cash prizes up for grabs:
Best in Show – $750
2nd Place – $500
First-Time Painter in a Plein Air Festival – $250
People’s Choice – $500
Historic/Residential Architecture – $350
Best Painting in the Oak Park Arts District - $350
Coolest Urban Vibes – $250
Best Use of Color – $250
Registered artists can enter as many categories as they like, and many will be working toward multiple pieces over the weekend. For the public, this means you’ll see a variety of styles and subjects, from finely detailed architectural renderings to bold, loose cityscapes bursting with energy.
The Grand Finale: Closing Reception and Art Sale
Circle Sunday, September 7, 3–6 p.m. on your calendar. That’s when all the freshly painted pieces will gather under one roof at the Nineteenth Century Club for the festival’s closing reception.
You’ll have the chance to:
See every piece up close and marvel at how artists interpreted familiar Oak Park corners in wildly different ways.
Cast your vote for the People’s Choice Award.
Purchase original artwork to take home (and yes, these are one-of-a-kind pieces created right here during the festival).
If you’ve ever wished you could buy a painting of your favorite neighborhood coffee shop or that sunny bench in Austin Gardens, this is your moment.
For the Artists: How to Join In
If you’ve been itching to set up your easel in public, this is your invitation. Artists can register now through the Eventbrite page.
Registration: Purchase one ticket per artist, valid for the entire weekend.
Selling at the Reception: Use the “Add-on” button during registration to reserve a table for selling your work on Sunday.
Questions? Email taz@oakparkareaartscouncil.org for details.
Over 20 artists have already signed up and there’s room for more. Whether you’re a seasoned plein air painter or trying it for the first time, Oak Park’s blend of architectural beauty and urban energy is the perfect backdrop.
Why Oak Park Is the Perfect Canvas
Oak Park is a patchwork of visual stories. Frank Lloyd Wright’s masterpieces stand alongside Victorian charmers. Tree-lined streets give way to lively café patios. Murals and shop signs pop against century-old brick. And because the festival takes place in early September, you’ll get that sweet spot between summer’s warmth and fall’s crisp air, ideal for painting (and strolling).
The mix of subjects means there’s something for every artist’s style:
Detail lovers can get lost in the angles and shadows of Wright-designed eaves.
Color chasers can focus on late-summer blooms or the cool tones of shaded park benches.
Urban storytellers can capture the steady rhythm of life downtown.
For visitors, it’s a chance to see the familiar through someone else’s eyes, maybe even spotting a building, a corner, or a garden you’ve never noticed before.
Tips for Enjoying the Festival
For spectators:
Bring a camera (or your phone) to snap your favorite works in progress.
Chat with the artists; most love talking about their process.
Make a weekend of it: Grab coffee at one of our indie cafés before a morning stroll, or finish your art walk with dinner alfresco.
For artists:
Pack light but smart; you’ll be moving around town.
Plan for the weather; September can swing from sunny to breezy.
Explore beyond the “big name” spots—Oak Park’s alleys, back gardens, and side streets hold plenty of surprises.
Mark Your Calendars!
The Oak Park Plein Air Festival is set to become a new tradition—one that blends art, community, and the beauty of being outside. Whether you’re here to paint, to buy, or simply to wander, you’ll leave with fresh eyes for the place we call home.
Dates: September 5–7, 2025
Closing Reception and Sale: Sunday, September 7, 3–6 p.m., Nineteenth Century Club
Artist Registration: Sign up here
Bring your curiosity and your walking shoes, because Oak Park is about to become one big, beautiful canvas.
Click here to see the map of painting locations.
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