East Bay Events: May 2026

If you’re searching for the best things to do this spring, May is packed with exciting events across the East Bay. From wine country festivals and family-friendly street fairs to shopping pop-ups, concerts, brunches, youth performances, sporting events, and community celebrations, there is something happening nearly every day this month.

Whether you live in Pleasanton, Livermore, Dublin, Walnut Creek, Danville, and Concord, or anywhere nearby, May is one of the best times of year to explore everything the East Bay has to offer. The weather is warm, outdoor patios are full, and local calendars are packed with activities for all ages.

This guide highlights the top events happening throughout May 2026 in the East Bay, organized in chronological order so you can plan your weekends and discover new local experiences.

Why May Is the Perfect Time to Explore the East Bay

There’s something special about May in the East Bay. Spring is in full bloom, the hills are still green, and communities across the region come alive with outdoor events and seasonal celebrations.

From the vineyards of Livermore to the shopping districts of Walnut Creek and the family events of Pleasanton, May showcases everything people love about the East Bay. It’s a month filled with energy, connection, creativity, and local pride.

The variety is what makes the East Bay so unique. In one weekend, you can enjoy a wine tasting, shop a handmade market, attend a live theater performance, and spend the next day at a street festival. Few places offer as much diversity in entertainment and lifestyle as the East Bay.

May 1: Chardonnay Celebration at Wente Family Vineyards

The month begins in Livermore wine country with the Chardonnay Celebration at Wente Family Vineyards.

This elegant event is perfect for wine lovers looking to experience one of the most iconic wineries in the East Bay. Guests can enjoy exceptional Chardonnay, scenic vineyard views, and the relaxed luxury that makes Livermore such a standout destination.

Wine events like this are one of the many reasons people love springtime in the East Bay.

May 1: SPARC Presents The Glass Menagerie

Also beginning May 1 is SPARC’s production of The Glass Menagerie at Bankhead Theater.

The Bankhead Theater is one of the premier performing arts venues in the East Bay, and this production is a great opportunity to enjoy live theater close to home. Events like this show how strong the arts scene is throughout the East Bay.

May 2–3: Spring Piano Recital at Lesher Center for the Arts

Families and supporters of youth arts can attend The Ballet School Performing Arts' Spring Piano Recital at Lesher Center for the Arts.

This recital celebrates student talent and creativity while bringing families together in one of the most respected arts venues in the East Bay. Supporting local youth performances is a meaningful way to connect with the community.

May 2: Kentucky Derby at Alameda County Fairgrounds

Horse racing fans can celebrate the Kentucky Derby at Alameda County Fairgrounds.

This popular annual gathering brings the energy of race day to the East Bay, complete with festive outfits, themed drinks, and a lively social atmosphere. It’s one of the more unique spring events in the region.

May 2: Evening at the Races at Elks Lodge

For another race-themed experience, Evening at the Races at Elks Lodge offers a fun and community-focused event.

Local gatherings like this are part of what makes the East Bay feel connected and welcoming.

May 2: Girls Crushing It Spring Pop-Up

Broadway Plaza hosts the inspiring Girls Crushing It Spring Pop-Up at Broadway Plaza.

This empowering event features more than 50 young entrepreneurs ages 8–18 showcasing their businesses. Guests can shop handmade products, gifts, décor, jewelry, skincare, pet products, and more while supporting the next generation of leaders in the East Bay.

With free face painting, music, and family-friendly energy, this is one of the most uplifting events of the month.

May 5: Line Dancing Class at Wood Family Vineyards

Looking for something interactive? Head to Wood Family Vineyards for a line dancing class.

This fun evening combines music, movement, and a beautiful vineyard backdrop. It’s another great example of how the East Bay offers experiences beyond the typical dinner-and-a-movie outing.

May 7: Danville’s Sip and Stroll 2026

Downtown Danville comes alive with Danville’s Sip and Stroll in Downtown Danville.

This favorite East Bay event blends wine tasting with boutique shopping and a walkable downtown setting. It’s the perfect night out for couples, friends, or anyone who enjoys supporting local businesses while exploring a charming downtown district.

May 9: Hello Kitty Café Truck at Broadway Plaza

Fans of all ages can visit the Hello Kitty Café Truck at Broadway Plaza.

This beloved pop-up brings themed treats and exclusive merchandise to the East Bay, making it a fun stop for families, collectors, and anyone looking for a playful outing.

Because it’s a limited-time event, it’s expected to draw strong crowds throughout the day.

May 9: McGrail’s Mother’s Day Sip & Shop

Mother’s Day weekend begins with McGrail’s Mother’s Day Sip & Shop at McGrail Vineyards.

Guests can browse local vendors, enjoy wine, and celebrate the holiday in a scenic setting. It’s one of the most popular Mother’s Day experiences in the East Bay.

May 9: A Tribute to The Bee Gees

Music lovers can enjoy A Tribute to The Bee Gees at Wood Family Vineyards.

Classic songs, vineyard views, and a fun crowd make this one of the most entertaining concert experiences happening in the East Bay this month.

May 9: Mariachi Divas de Cindy Shea

For a vibrant live performance, Mariachi Divas de Cindy Shea take the stage at Bankhead Theater.

Their high-energy show adds cultural richness and variety to the May event calendar in the East Bay.

May 10: Mother’s Day at Cuda Ridge Wines

Celebrate Mother’s Day in Livermore at Cuda Ridge Wines.

This relaxed winery setting offers a beautiful and memorable way to spend time with family while enjoying one of the most scenic parts of the East Bay.

May 10: Mother’s Day Brunch at Wente

Another standout celebration is Mother’s Day Brunch at Wente Family Vineyards.

Combining excellent food with vineyard views, this event is one of the most sought-after holiday outings in the East Bay.

May 10: HEAD WEST Marketplace

Shop local at the HEAD WEST Marketplace in Walnut Creek from Bonanza to Mt. Diablo.

This open-air market features handmade ceramics, vintage finds, local brands, and artisan goods. Events like this help small businesses grow while creating a fun shopping experience for the East Bay community.

Outdoor markets continue to be some of the most popular spring activities in the East Bay.

May 15: East Bay Jazz 10th Anniversary Concert

Music continues mid-month with the East Bay Jazz 10th Anniversary Concert at Bankhead Theater.

This milestone concert celebrates a decade of jazz and brings incredible talent to one of the top music venues in the East Bay.

May 16: Livermore Downtown Street Fest

One of the biggest events of the year begins May 16 with the Livermore Downtown Street Fest in Downtown Livermore.

This iconic festival features live music, food vendors, shopping, entertainment, and a lively crowd. It’s one of the signature annual traditions in the East Bay and a must-visit weekend event.

May 16–17: Preakness Stakes at Alameda County Fairgrounds

Also on May 16, racing fans can return to Alameda County Fairgrounds for the Preakness Stakes celebration.

It’s another fun social outing and a great way to enjoy spring in the East Bay.

May 16: Once Upon a Street – Beauty & Bouquets

Broadway Plaza hosts Once Upon a Street: Beauty & Bouquets at Broadway Plaza.

This themed spring celebration includes live DJ entertainment, bouquet making, face painting, and family-friendly activities. It’s a cheerful and creative event that adds even more excitement to the May calendar in the East Bay.

May 23–24: Valley Dance Theatre’s Spring Rep 2026

The performing arts continue with Valley Dance Theatre’s Spring Rep 2026 at Bankhead Theater.

This performance showcases creativity, movement, and local talent, reinforcing why the East Bay has such a thriving arts culture.

May 23: Makers Market Outdoor Market

Broadway Plaza also hosts the Makers Market Outdoor Market on May 23 at Broadway Plaza.

This free event features local artists, handcrafted goods, eco-friendly products, jewelry, candles, honey, apparel, and more. With live music and nearby dining, it’s an ideal way to spend a spring afternoon in the East Bay.

Shopping local events like this are a big part of the community spirit that defines the East Bay.

May 27: Pleasanton RAGE USL W League Theme Nights and Matches

Sports fans can enjoy local soccer action with Pleasanton RAGE USL W League Theme Nights and Matches.

Supporting local teams is a fun and energetic way to connect with the East Bay community while enjoying high-level competition.

May 30: FuelFest Bay Area

Car enthusiasts won’t want to miss FuelFest Bay Area at Alameda County Fairgrounds.

This high-energy event features custom cars, entertainment, vendors, and festival excitement. It draws visitors from across Northern California and turns Pleasanton into one of the most exciting destinations in the East Bay for the day.

May 31: Views in the Valley Photo Competition 2026

Closing out the month is the Views in the Valley Photo Competition in Livermore Valley Wine Country.

This creative event celebrates the landscapes, vineyards, and natural beauty that make this part of the East Bay so special.

All Month Long: Mary Poppins JR

Throughout May, families can enjoy PYTC presents Mary Poppins JR at Firehouse Arts Center.

This family-friendly production is a great example of the strong youth arts programs and community involvement found across the East Bay.

Final Thoughts on May in the East Bay

May is one of the most exciting times of year in the East Bay. With festivals, markets, concerts, brunches, sporting events, performances, and family activities filling the calendar, there are endless ways to enjoy the season.

Whether you’re sipping wine in Livermore, shopping in Walnut Creek, enjoying a show in Pleasanton, or discovering a new tradition with friends and family, there’s no shortage of reasons to get out and experience the East Bay this month.

If you’ve been looking for the perfect time to explore more of what makes this region special, May is it in the East Bay.