Best Things to Do on the Monterey Peninsula This May

Perhaps it’s part of a greater pattern of reopening and reorienting, but this month of May on Monterey Bay feels like an arrival of sorts.

A couple of the year’s top wine festivals, a major art explosion, outdoor markets, a wild unicorn-and-fairy party in the woods, a few wine strolls, and the most anticipated music festival of the year — or, because of COVID, the last three years — help galvanize that feeling.

As dynamic as the attractions can be, the same can be said for late springtime weather, so pack appropriately to prevent any weird fog or rain patterns from scaring away the chance to play.

Featured Photo: Meritt Thomas on Unsplash
monterey peninsula, santa cruz downtown wine walk
Photo: @downtownsantacruz / instagram

Downtown Santa Cruz Spring Wine Walk

May 1

Handpicked participating wineries, the vast majority hailing from the Santa Cruz Mountains, pour tastings at a range of downtown Santa Cruz shops. Limited tickets make for more dynamic and deepened enological education and a map helps streamline the springtime soiree.

More info:

monterey peninsula, ron white
Photo: @ronwhiteofficial / instagram

Ron White at Golden State Theatre

May 6

The credentials are objectively robust: All of his comedy albums charted #1 on the Billboard Comedy Charts. He’s sold over 14 million albums (solo and with the Blue Collar Comedy Tour he helped start), been nominated for two Grammys, and long been one of the top grossing stand up comedians on tour in America. But he’s still most famous for the cigar and Scotch on stage. As long as you’re laughing, Ron White could care less. 

More info:

Photo: @firstfridaysantacruz / instagram

First Friday Santa Cruz

May 6

The avalanche of arts open houses sprawls across multiple districts, from Westside to Eastside, downtown to Midtown, the Tannery Arts Center to Felton, Ben Lomond and beyond. Popular FF destinations include Radius Gallery, Santa Cruz Art League, Treehouse Dispensary and Santa Cruz Mountains Art Center. More on where to go and what to expect for the free event via its website.

More info:

monterey, peninsula, annual wine celebration
Photo: Courtesy of Manny

29th Annual Monterey Winemakers' Celebration

May 7

This time-honored event is certainly one for wine lovers to short list. The legion wineries of the Monterey County Vintners and Growers Association — around 40 all told — populate leafy Devendorf Park in the heart of Carmel-by-the-Sea, complemented by local chefs cooking al fresco. One of the very best wine festivals of the year.

More info:

monterey peninsula, capitola village sip and stroll
Photo: Capitola Village Facebook

Capitola Village Mother’s Day Sip & Stroll

May 7

The storybook setting that is beachside Capitola Village plays host to a five-hour choose-your-own adventure featuring a welcoming flow of venues and a total of 12 tickets for 2-ounce pours. The generous time window makes it easy — and advisable — to build in some stops by the beach or little Capitola’s mighty selection of restaurants. Friends can tag along and do not need tickets if they are not tasting.

More info:

monterey peninsula, roaring camp railroad
Photo: @bennys_journey / @roaringcamp / instagram

Roaring Camp Railroad’s Mother’s Day Brunch

May 8

RCR presents a solid way to shower Mom with maximum love: start with brunch organizers describe with one word (“delectable”), enjoy live music by Pat Hull, and then take a relaxing ride on the train through the soaring redwoods. Bonus: The kids can hit the craft table to make something memorable for Number One Mom too.

More info:

Photo: Carmel Village Facebook

Carmel Art Festival

May 13-15

Sixty juried artists paint for two days on location and then display and sell their work at the festival over the weekend. The since-1993 free event includes a pay-to-play VIP wine option with a sneak preview of the available art, Quick Draw, sculpture, kids arts activities and more. Set in historic Devendorf Park.

More info:

monterey peninsula, santa cruz
Photo: Brothers Promotions Facebook

West Cliff Outdoor Market 2022

May 14

Unique artisans + food trucks + clifftop views of the ocean and Steamer Lane surf spot = Santa Cruz springtime magic. The free-admission affair fills two parking lots with all sorts of hand-crafted art, jewelry, gifts and food-and-drink vendors.

More info:

monterey peninsula, masquerade
Photo: Llanydd Lloyd on Unsplash

Fae Masquerade Ball: Welcome to the Realm

May 14

What is Fae? “Fae is all things magical,” its organizers report. “It’s where fairies, mermaids and unicorns come from. Not just fairies but all magical creatures. Greenman, werewolves, wizards, pixies, mermaids, unicorns, trolls, fauns, valkyrie, and so many more.” This celebration at Brookdale Lodge invites them all out to play. According to the event page at, “Your imagination is the only limit. Dust off your fairy wings. Polish your horns. It’s time to celebrate.”

More info:

monterey peninsula, california roots
Photo: California Roots

California Roots Music and Arts Festival

May 21

Dirty Heads, Stephen Marley, Demarco, Alborosie, Denm, Fortunate Youth, Tropedelic and many more lead the way for the internationally known reggae rock festival where the puffs of smoke are only outsized by the tidal waves of sound and massive positive vibes. Three days of music headline, but there are many other draws to dip into, with extensive art displays, workshops, interactive exhibits and a wealth of food and drink options, all done with a dedication to sustainability. 

More info:

Looking for more things to do in the area?

Visit our What to Do in Northern California page!

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