Best Things to Do on the Monterey Peninsula This May

Best Things to Do on the Monterey Peninsula This May

Little ol’ Monterey Peninsula has a gift for festivals with big ol’ influence, especially when it comes to music. Note the Monterey Pop Festival and Monterey Jazz Festival, and now California Roots Music and Arts Festival, better known simply as Cali Roots.

Having connected artists and rollicking crowds since 2010, Cali Roots has vibed its way into its position as the preeminent reggae-roots-rock gathering in the country — and beyond — with the blazing lineup, complementary attractions and far-flung fan pilgrimages to affirm that. 

The Roots’ revival helps herald the start of event season around these Peninsular parts. Here appears more on that and other recommended events for the month.

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: Quail Motorcycle Gathering
The Quail Motorcycle gathering in Monterey, California.
Photo: Courtesy of Quail Motorcycle Gathering

The Quail Motorcycle Gathering

May 4

Upwards of 300 vintage and modern cycles — bicycles, scooters and (mostly) motorcycles — fill the grass at the expansive Quail Lodge & Golf Club in bucolic Carmel Valley. This year’s headlining elements are the 30-year anniversary of the Ducati 916, 25th anniversary of the Suzuki Hayabusa, the 100th anniversary of the American Motorcyclist Association, and a special celebration of the Vespa, across decades of rolling in style. Gourmet lunch stations, local wines, retail exhibitors and lifestyle brands all round out the action.

More info:

Do_monterey peninsula_may_1200_Monster Trucks CREDIT Gabriel Tovar
Photo: Courtesy of Gabriel Tovar

Monster Jam at Salinas Sports Complex

May 5

This Sunday service releases some high octane sound and action. The opening Monster Jam Pit Party revs up the interaction for fans to see the massive rides up close, meet their favorite drivers and crews, get autographs and take pictures. From there roars hours of high-flying and heavy-impact intensity — one wouldn’t think 12,000-pound trucks could do what they do in such smashing ways, but they do roll out names like Grave Digger, Megalodon and Rammunition for a reason.

More info:

Do_monterey peninsula_may_1200_Carmel Art Festival CREDIT Yannis Papanastasopoulos
Photo: Courtesy of Yannis Papanastasopoulos

Carmel Art Festival

May 17–19

CAF launches into its fourth decade with three days of exhibition paintings at Devendorf Park, with five dozen artists participating, and live painting on site at scenic spots all around host Carmel-by-the-Sea and the rest of Monterey Peninsula. Live entertainment, “quick-draw” sessions, Sculpture-In-the-Park displays and special VIP events find vivid expression too.

More info:

Do_monterey peninsula_may_1200_Sun, Wind & Wine
Photo: Courtesy of Sun, Wind & Wine Festival

Sun, Wind & Wine Festival

May 18

Belle Glos. Bernardus Winery. Bruliam Wines. Caraccioli Cellars. Cattleya Wines. Clarice Wine Company. CRU Winery. hope & grace. Integrity Wines. J. Lohr Vineyards & Wines. Joyce Wine Company. Kori Wines. Landmark Vineyards. Luli Wines. McIntyre Vineyards. Mer Soleil. Miner Family Winery. Mooney Family Vineyards. Morgan Winery. Odonata. Pessagno. Pisoni Vineyards. Puma Road Winery. ROAR Wines. Rombauer Vineyards. Rustique Winery. Sarah’s Vineyard. Scheid Family Wines. Siduri |Talbott Vineyards. Testarossa. Three Furies Wines. Tondre Wines. Tudor Wines. Wrath. The roughly 20 chefs and food purveyors, wine country setting and see-and-be-seen scene bear mentioning too, but here it’s all about the incredible lineup of Santa Lucia Highlands wineries ready to pour their hearts out.

More info:

Do_monterey peninsula_may_1200_Winery Passport CREDIT Kym Ellis
Photo: Courtesy of Kym Ellis

Santa Cruz Mountains Passport Days

May 18

The award-winning SCM wineries design one-off tasting experiences in the climate and soils that make for great vino. Ticket holders enjoy tasting flights at each participating winery, and access to exclusive events and discounts throughout the rest of the year. Integrity, Inversion, Left Bend, La Honda, Muns, Martin Ranch, Saison, Storrs, and dozens more let the lofty flavor flow.

More info:

Group of friends toast wine at Santa Cruz Wine Walk in May
Photo: Courtesy of Manny

Downtown Santa Cruz Spring Wine Walk

May 19

“What’s better than wine tasting?” wine walk organizers ask, revisiting the event’s time-honored refrain. “Wine tasting in downtown Santa Cruz!” As a plethora of Surf City’s unique boutiques partner with local wineries for stroll-sip-stroll inspiration, a wristband and a wine glass represent all the equipment needed: Maps are helpful (and available), but so many spots participate within the downtown area that the choose-your-own-adventure requires very little decision-making. It also helps the superb wineries representing come without a weak link.

More info:

Musician onstage at California Roots Passport in Monterey, California
Photo: Courtesy of Josue Rivas

California Roots Music and Arts Festival

May 24–26

The music is substantial, as a deep list of 30+ acts like Ice Cube, Lupe Fiasco, The Green, Souls of Mischief, Tribal Seeds, E-40, Pepper and multiple Marleys (Damian Jr. Gong, Stephen and Ziggy among them) demonstrate. And a lot more than music awaits, with Interactive art displays, workshops, exhibits, artisan goods, merch and an avalanche of food and drink options fill the storied Monterey County Fairgrounds. 

More info:

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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