Best Things to Do on the Monterey Peninsula This May

Every month, something big happens in one of the Monterey Peninsula’s tiniest towns.

Sand City, population 328, packs at least that many people into its central Art Park every first Friday. That’s when Night Market 831 electrifies its audience by way of live performance, interactive art, food trucks, beverages of craft variety and an overload of on-site and surrounding urban mural art.

Every year, something massive happens at the one of the area’s most legendary venues, the same fairgrounds that hosted Monterey Pop Festival: The California Roots Music and Art Festival. 

It has quickly grown into a world-class festival with a lineup that wows by way of quality (headliner voltage) and quantity (multiple stages will be saturated with top groups, see below).

Locally sown and locally owned Good Vibez Entertainment puts on both events — which feels like a promising omen for a May slate of events transmitting lots of positive vibes. 

Looking for the coolest things to do on the Monterey Peninsula? We’ve got you covered. From top wine festivals, to a major art explosion, outdoor markets, and the most anticipated music festival of the year. We’ve done the deep research for you on the best things to do on the Monterey Peninsula including museums, cultural events, food tours, golfing, hikes and more. Speaking of food, we also have an extensive list of our best restaurants on the Monterey Peninsula, and if you’re planning a weekend, the the best places to stay

Featured Photo: Carmel Art Walk
neon sign at night market 831
Photo: @firstfridaysantacruz / instagram

Night Market 831

TGIF, Sand City style: The colorful Monterey Bay capital for community art plays host to a monthly explosion of food trucks and vendor tables, artisan creators, family-friendly creative activities, live music and craft beer. Touring the neighborhood’s big-format graffiti commissioned by the city, which paint in every direction, is recommended.

More info:

night time at first fridays in santa cruz
Photo: Courtesy of Visit Santa Cruz County

First Friday Santa Cruz

The monthly celebration comes by way of a constellation — of studio and workshop open houses across downtown and Midtown, Westside and Eastside, Tannery Arts Center and Felton, Ben Lomond and beyond. This installment may benefit from a little Cinco de Mayo spice to boot.

More info:

Photo: Courtesy of Quail motorcycle Gathering

The Quail Motorcycle Gathering

For 2023, one of the most anticipated motorcycle events of the year features a curated selection of Italian cycles, 1970s vintage muscle, “Bring on the Baggers” (IYKYK), alongside 11 other traditional classes. Meanwhile Bubba Shobert will be honored as a Legend of the Sport and participate in a highly anticipated interview, while gourmet tasting tables and the gorgeous Quail grounds help fill the field.

More info:

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

Downtown Santa Cruz Spring Wine Walk

Tasting tables materialize in an array of Surf City’s unique boutiques. A wristband plus a wine glass equal fluid flow of vino and fun. Maps are available, but there are enough solid spots within a dense network of destinations that they’re not necessary. Just keep wandering and experiencing. “What’s better than wine tasting?” wine walk organizers ask. “Wine tasting in downtown Santa Cruz!” 

More info:

Half Moon Bay Wine & Jazz Fest | Main Street

Wines by 50 California vintners, food by local restaurants, live performances by Bay Area jazz greats. 

More info:

Mothers Day-credit Bellina Caetano-800x450
Photo: Courtesy of Bellina Caetano

Mother's Day

Photo: Carmel Village Facebook

Carmel Art Festival

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Photo by Yifeng Lu

Santa Cruz Mountains Passport Days

A gaggle of high-grade wineries customize unique tasting experiences against the backdrop of the surrounding mountains. A tasting flight awaits ticket holders at each winery, as does access to exclusive events and discounts throughout the year. Bring on Bargetto and Beauregard, Fellom Ranch and Fernwood Cellars, Windy Oaks and Wrights Station, a half dozen standouts among three dozen all told.

More info:

california roots
Photo by Josuer Rivas

California Roots Music and Arts Festival

Memorial Day-credit Presidio Trust-800x450
Photo: Courtesy of Presidio Trust

Memorial Day

Event Venues

Looking to see what’s happening right now on the Monterey Peninsula? Our comprehensive list of venues across the city below will help you find what you need to know what’s going on.

Looking for more things to do in the area?

Visit our What to Do in Northern California page!

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