Tri-Valley Events: May 2026
Livermore Downtown Street Fest
If you’re looking for the best things to do this spring, May is packed with excitement across the Tri-Valley. From wine country celebrations and family-friendly festivals to horse racing watch parties, live theater, concerts, and community gatherings, there is something happening nearly every weekend. Whether you live in Pleasanton, Livermore, Dublin, Danville, or nearby, this month is one of the best times of year to explore everything the Tri-Valley has to offer.
As the weather warms up and the days get longer, residents and visitors alike head outdoors to enjoy festivals, vineyard events, arts performances, and seasonal celebrations. May is the perfect month to support local businesses, experience community culture, and discover why so many people love spending time in the Tri-Valley.
This guide covers all the major events happening this May in the Tri-Valley, with details on what to expect, why each event is worth checking out, and how to make the most of your month.
Why May Is One of the Best Months in the Tri-Valley
There’s something special about May in the Tri-Valley. The hills are still green, the vineyards are thriving, patios are buzzing, and local calendars are full of energy. It’s that sweet spot between spring and summer where the weather is ideal and the community comes alive.
May also showcases what makes the Tri-Valley so unique: a strong sense of community, a thriving local wine scene, and a packed calendar of events that cater to all ages and interests. From elegant wine tastings to lively street festivals, the Tri-Valley truly shines this time of year.
May 1: Chardonnay Celebration at Wente Family Vineyards
The month begins in style with the Chardonnay Celebration at Wente Family Vineyards. This event is perfect for wine lovers in the Tri-Valley, offering the chance to sample exceptional Chardonnay in one of the most scenic vineyard settings in the region.
Wente is one of California’s most historic wineries, and events like this highlight the rich wine culture that makes the Tri-Valley such a special destination.
May 1: SPARC Presents The Glass Menagerie
Also kicking off the month is SPARC’s production of The Glass Menagerie at Bankhead Theater. The Bankhead Theater is one of the premier arts venues in the Tri-Valley, and this production offers a fantastic way to enjoy a night of live theater close to home.
The arts community continues to be a major part of what makes the Tri-Valley vibrant and culturally rich.
May 2: Kentucky Derby at Alameda County Fairgrounds
Horse racing fans in the Tri-Valley can celebrate one of the sport’s biggest days at Alameda County Fairgrounds during the Kentucky Derby festivities.
Expect festive attire, themed drinks, and a lively social atmosphere. It’s a fun way for the Tri-Valley community to enjoy the excitement of race day without leaving the area.
May 2: Evening at the Races at Elks Lodge
For another racing-themed option, Evening at the Races at Elks Lodge offers a fun and casual community event in the Tri-Valley.
This is a great choice for those who enjoy local gatherings and social events with a spirited atmosphere.
May 5: Line Dancing Class at Wood Family Vineyards
Looking for something interactive in the Tri-Valley? Head to Wood Family Vineyards for a line dancing class.
This event combines movement, music, and a beautiful vineyard setting, making it one of the more unique ways to spend an evening in the Tri-Valley.
May 7: Danville’s Sip and Stroll 2026
Downtown Danville comes alive with Danville’s Sip and Stroll 2026 in Downtown Danville.
This popular Tri-Valley event blends wine tasting with boutique shopping and a walkable downtown atmosphere. It’s the perfect night out for those who enjoy exploring local businesses while sipping and strolling through town.
May 9: McGrail’s Mother’s Day Sip & Shop
Mother’s Day weekend begins with the Mother’s Day Sip & Shop at McGrail Vineyards.
This beloved Tri-Valley event combines wine tasting with local vendors, creating a fun and festive shopping experience where you can pick up gifts while enjoying the beauty of Livermore wine country.
May 9: A Tribute to The Bee Gees
Music lovers in the Tri-Valley can also enjoy A Tribute to The Bee Gees at Wood Family Vineyards.
With classic hits and a vineyard backdrop, this concert blends nostalgia and entertainment in one of the most enjoyable settings in the Tri-Valley.
May 10: Mariachi Divas de Cindy Shea
For a completely different musical experience, Mariachi Divas de Cindy Shea perform at Bankhead Theater.
Their vibrant performance adds diversity and cultural richness to the May entertainment calendar in the Tri-Valley.
May 10: Mother’s Day at Cuda Ridge Wines
Celebrate Mother’s Day in the Tri-Valley with a relaxing outing at Cuda Ridge Wines.
This winery setting offers a peaceful and memorable way to spend quality time with family while enjoying the scenic charm of the Tri-Valley.
May 10: Mother’s Day Brunch at Wente
Another standout option is Mother’s Day Brunch at Wente Family Vineyards.
Great food, vineyard views, and a festive atmosphere make this one of the most sought-after Mother’s Day experiences in the Tri-Valley.
May 15: East Bay Jazz 10th Anniversary Concert
Music continues mid-month with the East Bay Jazz 10th Anniversary Concert at Bankhead Theater.
This celebration of a decade of jazz brings exceptional talent and live performance energy to the Tri-Valley arts scene.
May 16–17: Livermore Downtown Street Fest
One of the biggest events of the month in the Tri-Valley begins on May 16 with the Livermore Downtown Street Fest in Downtown Livermore.
This festival features live music, food vendors, shopping, entertainment, and a lively community atmosphere. It’s one of the signature annual events that defines spring in the Tri-Valley.
May 16: Preakness Stakes at Alameda County Fairgrounds
Also on May 16, racing fans can gather again at Alameda County Fairgrounds for the Preakness Stakes celebration.
It’s another fun social event that adds variety to the Tri-Valley calendar.
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 event highlights the talent and creativity found throughout the Tri-Valley, offering audiences an inspiring live performance experience.
May 27: Pleasanton RAGE USL W League Theme Nights and Matches
Sports fans can enjoy local soccer action on May 27 with Pleasanton RAGE USL W League Theme Nights and Matches.
Community sports are an important part of life in the Tri-Valley, and this is a great chance to support local athletes while enjoying an energetic evening.
May 30: FuelFest Bay Area
Car enthusiasts across the Tri-Valley will want to mark their calendars for FuelFest Bay Area at Alameda County Fairgrounds.
This high-energy event features custom cars, entertainment, and a festival atmosphere that draws visitors from all over Northern California to the Tri-Valley.
May 31: Views in the Valley Photo Competition 2026
Closing out the month is the Views in the Valley Photo Competition 2026 in Livermore Valley Wine Country.
This creative event celebrates the natural beauty of the Tri-Valley, encouraging photographers to capture the landscapes, vineyards, and charm that make the region so unique.
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 another example of the strong arts and youth programs that thrive in the Tri-Valley.
Final Thoughts on May in the Tri-Valley
May is one of the most exciting times of year in the Tri-Valley. With festivals, concerts, wine events, performances, sports, and family activities filling the calendar, there are endless ways to enjoy the season.
Whether you’re attending a vineyard brunch, exploring a downtown festival, cheering at a match, or discovering a new local tradition, there’s no shortage of reasons to get out and experience the Tri-Valley this month.
If you’ve been looking for an excuse to explore more of what makes this region special, May is the perfect time to do it in the Tri-Valley.
