Palo Alto Festival of the Arts – Italian Street Painting

Italian Street Painting - Palo Alto Festival of the Arts

Italian Street Painting Expo: Chalk Art Paintings Come to Life on Tasso

Palo Alto Festival of the Arts attendees will have two full days to become immersed in some exceptional visual and performance art throughout the nine-block festival. For the 18^th year, Tasso Street will once again provide the canvas for the popular Italian Street Painting Expo, in which 100-square-foot and larger chalk pastel paintings by world-renowned chalk artists will be created on the asphalt over the festival’s run. And kids can get involved, too, by creating their own chalk canvases in the special Chalk-a-Lot area.

The Italian Street Painting Expo will amaze visitors with a variety of themes that reflect each artists’ passion of this unique art form. Replicas from Old Masters to anamorphic styles (artwork that appears three-dimensional) will cover one full block on Tasso.

This Italian tradition dates to the 1500s where street painters became known as Madonnari for creating images of the Madonna on public streets. It has since flourished throughout Europe and the United States, bringing many more innovative artists to the scene to try their hand at chalk painting, or pavement art as it’s known in England.

2025 Featured Artists: Cheryl and Wayne Renshaw

Husband-and-wife team Wayne and Cheryl Renshaw are this year’s Featured Artists. They have participated in every Palo Alto Festival of the Arts Italian Street Painting Expo since it began.

“We started on this grand ‘street painting’ adventure 25 years ago at a festival in Santa Barbara,” Wayne said. A dozen friends tried it out together. “The goal was to get more chalk on the ground than on each other – which we achieved with a questionable amount of success. A good time was had by all.” The Renshaws chalked with this group for a couple of years and then branched out on their own.

“The chalking community (or the “tribe” as it has come to be known) is a very welcoming community,” Wayne said. “Most artists know each other and are happy to share their tips and techniques. In fact, it is common for artists to jump in and assist other artists finish their work, due to rain, sickness, etc.”

Cheryl Renshaw & Wayne Renshaw
12' x 15'

Street painting is a hobby that they found they can do together. “We both enjoy art, drawing, painting and design,” he said. “We bring different, yet compatible skills to the package so it works for us.” They have participated in festivals throughout the United States, Canada and Mexico.

As much as they enjoy street painting, they still have day jobs: Wayne is an architect, running his own office in Santa Clara, and Cheryl is a landscape designer who also works at Gamble Garden in Palo Alto as “Plant Geek.”

Their chalk art this year will pay tribute to the February 2026 Winter Olympics in Milan and Cortina d’Ampezzo, Italy. “Part of the process of doing a street painting is coming up with an image to draw, and there is no shortage of exciting things to draw when using the Olympics as a theme,” Wayne said. “For this project, we will be focusing on the unique setting of the Italian landscape and the alpine skiers flying down the mountain side.”

Their chalk art will be in an “anamorphic” or “3D” style. “We introduce distortions into the image in order to make it appear as if the skier is flying right in front of you,” he said.

More Amazing Chalk Artists

Along with Wayne and Cheryl, 16 more amazing chalk artists are participating this year in 100-square-foot and larger street canvases. See the full list below.

This year, all the chalk artists will feature a heart somewhere in their designs, in memory of former longtime Palo Alto Festival of the Arts executive director Mary Lou Atkins, who passed away earlier this year.

Proceeds from the sponsored-street paintings will go to support Ada’s Café, whose main priority is to create engaging and meaningful career experiences for adults with disabilities.

Kids’ Chalk-a-Lot

The Kids’ Chalk-a-Lot area, toward the end of Tasso near Lytton, allows youths to purchase for a nominal fee a 2x2-foot asphalt canvas to create their own chalk art. The Kids’ Chalk-a-Lot area will benefit Youth Community Service.

Non-Profit Beneficiaries and Sponsors

The Italian Street Painting Expo gives two local non-profits, Ada’s Café and Youth Community Service, the opportunity to raise funds to implement community service programs. Be sure to stop by to support both worthy organizations.

Monies raised from the sponsored artists’ street paintings will benefit Ada’s Café, whose main priority is to create engaging and meaningful career experiences for adults with disabilities.

The Kids’ Chalk-a-Lot area will benefit Youth Community Service, which elevates youth voice to raise community connection and equity through service.

A big thank-you to our Italian Street Painting Expo Community Sponsors: Anne Barry; Todd Cerf & Family; Common Roots Farm; In Loving Memory of Margaret Florsheim: Frome Family Foundation; Sue Garadis; Gidaro Family; Hahn Family; Klausner Family; National Charity League; Oftedal-Macquarie Family; Ellyn P.; Palo Alto Community Fund; Palo Alto Rotary; PA University Rotary in Honor of Mike Teutschel; Pathways: Belong, Believe, Become; and Wisteria Foundation.

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