May 2 – Cloverdale Wine Walk
The first Saturday of each month, from October through May, features local businesses pairing with very local wineries. Guests enjoy lunch, which is included with the price of your ticket. There are also tickets at a lower cost ($20) for designated drivers. Your designated driver can still enjoy lunch and the stroll through downtown. Many businesses also feature baked specialties, other foods and music. Join us!
May 2 – Bloody Mary Challenge
Join Charbay Distillery and the Santa Rosa Fire Department for a bloody delicious showdown: the 2nd Annual Bloody Mary Challenge, where top local restaurants battle it out for the title of Best Bloody Mary in Sonoma County.
You’ll sip, sample, and vote your way through a lineup of uniquely crafted Bloody Mary’s, each with its own twist—while supporting the firefighters who keep our community safe.
What to Expect:
- A Bloody Mary tasting adventure from some of the most creative bars & restaurants in the region
- A people’s choice vote – you decide who takes home the trophy
- A lively, social atmosphere in the heart of Santa Rosa
- Delicious brunch vibes from Grossman’s and the historic Hotel La Rose
May 3 – Barndiva’s Pink Party
Meet the most exciting rosé wine producers in Sonoma & Mendocino counties! In true Barndiva fashion, there will be music, bites, and extraordinary florals.
Dress code: Think Pink!
1:00 pm – 4:00 pm
May 3 – Geyserville May Day
Celebrate spring with a good old-fashioned town picnic at the Geyserville Winery on Sunday, May 4th, 2025 from 11 AM to 4 PM.
Enjoy:
Live music from the band Pazifico
Family-friendly fun with kid’s activities and classic games
Local wine and beer
The always-popular Kiwanis Rib Cook-Off Competition.
May 7 – E40 at Graton
E-40 Live in The Event at Graton Resort & Casino.
Doors Open at 8:00 p.m.
Exclusive Bars Available Inside Concert Venue.
May 10 – Mother’s Day Brunch at SpoonBar! Healdsburg
May 10 – Mother’s Day Brunch at Orsi
Join us for a relaxed, Italian-style brunch featuring four of our favorite pours—Sparkling Biancolella, Fiano, Nebbiolo, and Sangiovese.
Wine club members enjoy $15 off—call or email us to receive your code.
We look forward to welcoming you and your family for a lively afternoon of great wine, delicious bites, and live music!
May 14-17 – Healdsburg’s Food and Wine Experience
Located in the heart of California Wine Country, the Healdsburg Wine & Food Experience is a weekend-long celebration featuring the best of Sonoma County and world-renowned food and wines. The festival will showcase the region’s makers: farmers, growers, winemakers and chefs, standing alongside globally recognized wines from the greatest wine regions of the world.
May 21-23 – Healdsburg Future Farmer’s Country Fair
Please join us for Healdsburg’s most anticipated community event of the year on May 21st -23rd, 2026 as we celebrate 77 years of supporting our local youth in agriculture.
Stay tuned for all the details to come — the Barn Dance, Fair schedule and entry information, the Twilight Parade, Livestock Auction, and so much more.
May 28 – Jessica Simpson at the Graton
Jessica Simpson first rose to fame with her powerhouse debut “I Wanna Love You Forever,” becoming one of the defining pop voices of the early 2000s with hits like With You, Take My Breath Away, and her platinum smash These Boots Are Made for Walkin’. Simpson released music in 2025 with Nashville Canyon Pt. 1 and Pt. 2, a bold blend of country, pop, rock, and Americana featuring standout tracks like Leave, Blame Me, and Fade. Her return was met with praise for its emotional honesty, raw storytelling, and commanding vocals, signaling that this chapter is not a comeback but a continuation of her artistic journey.
We hope to see you there!