Best Things to Do in Wine Country This May

Looking to fill a couple hours of your day while in Wine Country? With so many offerings in the area, we’ve curated the top events this month. Less researching and more having fun. Cheers!

Featured Photo: Bel R on Unsplash
wine country, california, bacchus landing
Photo: Bacchus Landing

“Sip & Savor Sundays” Food Truck Series at Bacchus Landing

Sundays through October 23rd

Wine, food truck favorites, picnic tables, bocce ball courts, and lawn games. Sounds like a great way to spend a Sunday!

More info: bacchuslanding.com

Photo: The Jim Henson Exhibit

Kendall-Jackson Inaugural Kentucky Derby® Party

May 7th

Celebrate the 148th Run for the Roses in Sonoma County Wine Country! Planned festivities include large-screen viewing of Kentucky Derby day races, an on-site milliner creating unique hats, Southern cuisine, and of course, wine. Event proceeds benefit Sonoma County’s Meals on Wheels program.

More info: kj.com

california, wine country, cheese festival
Photo: Kelly J Owen

California Artisan Cheese Festival

May 7th

After a two-year hiatus, this delicious celebration of California artisan cheese returns to Santa Rosa. Come hungry, there will be more than 100 award-winning cheeses to taste!

More info: artisancheesefestival.com

Photo: Ackerman Heritage House

Afternoon Tea at Ackerman Heritage House

May 7th – 8th

Sip organic tea while nibbling on finger sandwiches and sweet treats, steps from downtown Napa, at a Queen Anne Victorian that dates back to the late 1800s. Do we need to remind you Mother’s Day is coming?

More info: ackermanfamilyvineyards.com

wine country, california, castello grand barrel party
Photo: Misty Lane

The Grand Barrel Party at Castello di Amorosa

May 13th

Taste more than 30 wines, take part in a blind tasting challenge, and watch how wine barrels are made in a Tuscan-style castle. Along with seasonal bites, there will be live music and complimentary shuttles running to downtown Calistoga.

More info: castellodiamorosa.com

wine country, california, safari west
Photo: Will Bucquoy

Stars of the Sonoma Serengeti at Safari West

May 14th

This annual fundraiser in Santa Rosa — complete with wine, bites and wild encounters — supports educational programming for underserved children in schools and hospitals across the country. In-person tickets are limited, but folks are also welcome to tune in virtually.

More info: safariwest.com

wine country, california, healdsburg wine and food experience
Photo: Kristen Green

Healdsburg Wine & Food Experience

May 20th – 22nd

Celebrating the best of Sonoma County, the first-ever festival will showcase winemakers, chefs, farmers, and more. Events will be take place at a number of locations including the Montage Healdsburg.

More info: healdsburgwineandfood.com

wine country, california, bottlerock napa
Photo: Chromeo/ Demian Becerra

BottleRock Napa Valley

May 27th – 29th

The three-day music, wine and culinary festival features more than 75 musical acts, including headline artists Metallica, P!nk, Twenty One Pilots and Luke Combs.

More info: bottlerocknapavalley.com

wine country, california, chardonnay classic
Photo: Meritage Collection

Chardonnay Classic

May 20th – 22nd

It’s an entire weekend in Napa dedicated to a single varietal. Along with educational sessions, they’ll be themed meals, and countless tasting opportunities. 

More info: meritagecollection.com

california, wine country, pine ridge vineyards
Photo: Crimson Wine Group

Hike Pine Ridge Vineyards

May 21st

Learn about sustainable farming techniques during a moderately challenging hike through terraced hillside vineyards in Napa Valley’s Stags Leap District. The hike ends in the winery’s demonstration vineyard and includes a box lunch. Additional hikes are planned in June and July. 

More info: pineridgevineyards.com

wine country, california, sip and stroll yountville
Photo: Art, Sip & Stroll Yountville

Yountville Art, Sip & Stroll

May 21st

Strolling Yountville is fun any day, but this annual event takes it up a notch. More than 50 artists, wineries, and musicians will take over Washington Street.

More info: artsipstroll.com

Looking for more things to do in the area?

Visit our What to Do in Northern California page!

You so deserve a vacation. 

Subscribe to our newsletter and we'll make it easy for you.

Scroll to Top