Heart of Gilroy Wine and Art Stroll, April 18 2026

GILROY DOWNTOWN BUSINESS ASSOCIATION PRESENTS
A WONDERFUL EVENT IN THE HEART OF DOWNTOWN GILROY

Heart of Gilroy

WINE AND ART STROLL

APRIL 18, 2026

1:00–5:00 P.M.

Enjoy a beautiful day in Downtown Gilroy with local wine, art, food, music & more

Join us for a dynamic day of art, film, music, and community connection. Throughout the event footprint, guests will discover immersive activations, live performances, interactive art installations, and vibrant creative energy at every turn.

HIGHLIGHTS:

  • 20+ local wineries
  • (3) Delicious bites from restaurant partners
  • Food trucks and curated culinary offerings
  • 20 featured artists + interactive art
  • DJ & Silent Disco experience

Thank you, 2026 Heart of Gilroy Festival Sponsors!

Heart of Gilroy Wine & Art Stroll in Gilroy, California. May 5, 2025

Elevate your experience with VIP ACCESS

  • Interactive Photo Booth 
  • Artisan Grazing Board
  • Exclusive VIP Lounge Access
  • Complimentary Sparkling Wine
  • Live Pottery Wheel 
  • Live Music Entertainment
  • Curated Wine Tasting
Heart of Gilroy Wine & Art Stroll in Gilroy, California. May 5, 2025
Heart of Gilroy Wine & Art Stroll in Gilroy, California. May 5, 2025

The Annual Downtown Gilroy Wine Walk is back!

We’d love to invite you to enjoy the craftsmanship of local wineries amid vibrant artwork and the smooth melodies of local musicians.

Pour Stations

List of Pour stations for Heart of Gilroy 2026

Featured Installations & Experiences

Community Mural
An 8-foot by 4-foot collaborative mural led by Mike of Mike’s Signs. Guests are invited to participate and contribute to a shared work of art that will evolve throughout the day.

Hearthfire Clay — Live Activation
Experience live ceramic artistry in action as Hearthfire Clay demonstrates their craft.

Nicki Ashby — Live Activation Station
A dynamic creative station featuring live artistic engagement throughout the event.

Mime Performance
Cody Moore will present a live mime performance outside of the Art Wall installation.

Steve the Hat Artist
Working live throughout the event, Steve will create original artwork on canvas and wood cuts while tabling and selling his merchandise.

$5 Portraits
Quick, fun portrait sketches available for guests.

Green Screen Experience
Step into a film-inspired backdrop and become part of the scene in this interactive activation.

Silent Disco
A high-energy headphone dance experience where guests choose their channel and dance the evening away.

Listening Station (TBD)
A curated audio experience designed to highlight sound, storytelling, and creative expression.

Gilroy Historical Society Listening Booth

Step into Gilroy’s story.

As part of the Heart of Gilroy Wine & Art Stroll, the Gilroy Historical Society will host a special Listening Booth Experience, offering visitors a chance to hear the voices and memories of the community.

Through recorded interviews and short films, guests can listen to personal stories from people who grew up in Gilroy—sharing reflections about the town’s early days, family traditions, local businesses, and the moments that shaped the city over generations.

Using headphones and a laptop viewing station, attendees can pause during the stroll to experience these authentic oral histories and discover the rich heritage that continues to define Gilroy today.

Visitors will also have the opportunity to learn more about the Gilroy Museum and how the Historical Society preserves photographs, artifacts, and stories that celebrate the community’s past.

This interactive stop offers a meaningful moment to connect with the people and history behind the “Heart of Gilroy.”

Heart of Gilroy Wine & Art Stroll in Gilroy, California. May 5, 2025

The Heart of Gilroy Wine & Art Stroll is all about celebrating the convergence of art, wine, food, and music. Talented local artists  and artisan makers are a cornerstone of this event.

Gilroy Downtown Business Association invites you to celebrate the arts as you shop local artisan and culinary vendors at an event that promises a blend of creativity and community.

Participating Artists for Heart of Gilroy 2026

Stroll through Downtown, where you’ll find a variety of food trucks and vendors serving up everything from savory bites to sweet treats. But don’t stop there—Downtown Gilroy is home to amazing local restaurants offering everything from casual eats to full dining experiences. Whether you’re grabbing a quick bite or sitting down to savor a meal, there’s something delicious waiting for you at every turn.

Smash Burger

One More Reason to Get Your Tickets Today: 

Incredible Food

The Art & Wine Stroll is about more than great wine and art — it’s also a chance to enjoy an amazing lineup of local flavors.

This year we are excited to welcome some of the region’s favorite food trucks, serving up delicious bites throughout the event in the Gardener Parking Lot. Whether you’re craving tacos, burgers, or lobster, there will be something for everyone to enjoy.

Food Truck Lineup

Big Sur Taco
Known for bold coastal flavors and fresh ingredients, Big Sur Taco serves up vibrant street-style tacos that are packed with flavor and perfect for strolling.

Uncle Pappas
A crowd favorite bringing comfort-food classics with a gourmet twist. Their menu offers hearty, satisfying options that pair perfectly with an afternoon of wine tasting.

 

Smash Burgers
Crispy-edged, juicy burgers cooked to perfection. Smash Burgers are all about big flavor and simple ingredients done right.

Cousins Maine Lobster
Nationally recognized and loved for their authentic Maine lobster rolls, this truck delivers buttery lobster, fresh seafood flavors, and a taste of the East Coast right here in Gilroy.

Talented musicians and entertainers are lined up to provide the perfect ambiance to sip & stroll in Downtown Gilroy. Join us for a beautiful weekend!

Community Stage

Heart of Gilroy Wine & Art Stroll in Gilroy, California. May 5, 2025

See you there!

Additional Info

Amber Atteberry, Event Chair: heartofgilroyfestival@downtowngilroy.com