The sun is out and Santa Cruz County events are in full swing. Below, you’ll find some of the month’s features from Lookout and our partners. Be sure to explore our BOLO events calendar for more things to do in Santa Cruz County.

Join us as a member to get exclusive access to our correspondent-led events and gain unlimited access to all our stories both on the website and app.

Additionally, Lookout collaborates with our Marketing Partners to promote significant community events. For more details about our Media Sponsorship program, feel free to reach out to my colleague Duffy Barrett at duffy@lookoutlocal.com. 

HIGHLIGHTED EVENT

May 24: Extra Tasty Tour – “Sweet” Dessert Festival 

Collective Santa Cruz brings the social scene alive through unique events and partnerships with local businesses. This summer, it will be hosting five major festivals with hundreds of amazing food, drink and creative businesses right here in Santa Cruz! Lookout is proud to be a media sponsor of this series. Each festival has a different taste theme, with May’s event centered on sweetness. Started by two Santa Cruz natives, come celebrate the kick off to the tour with Collective’s dessert festival. If you are a small business owner and would like to be part of the lineup, apply at Collective Santa Cruz. Calling all Lookout members – be on the lookout for some EXTRA sweet events with Lily Belli around the festivals, too.

MORE EVENTS

May 8: Pajaro Valley Chamber Cornhole Tournament

The Pajaro Valley Chamber of Commerce and Agriculture is hosting a cornhole tournament! This is a chance to show off your cornhole skills and engage in friendly competition. There will be food, music and prizes. Donations from this event will go to Second Harvest Food Bank of Santa Cruz County. Join us for this event at the GaryAir Hangar at Watsonville Muni Airport. 

May 9: 2025 Santa Cruz Small Business Summit

For the second year in a row, Lookout is proud to be a media sponsor for the Small Business Summit hosted by the Santa Cruz County Small Business Development Center. Join more than 200 local small business owners at Cabrillo College’s Samper Recital Hall in Aptos to share best practices, learn about industry trends and connect with like-minded local entrepreneurs. 

May 9: Scott’s Valley Chamber Awards Gala

Join the Scotts Valley Chamber of Commerce at Roaring Camp’s Bret Harte Hall for its annual Community Awards Gala. Lookout is proud to be a media sponsor for this event as we work to honor the individuals and organizations that help our beloved city thrive. The 2025 theme, “Passport Around the World,” will take guests on an international journey as we celebrate Woman of the Year, Youth of the Year and more. This is your invitation to connect with local neighbors, have fun and give back to your city. 

May 14: Be the Difference Awards – Volunteer Center

Hosted by the Volunteer Center of Santa Cruz County, the Be the Difference Awards celebrate the volunteers, organizations and businesses that make our community stronger through exceptional service and dedication. Each year, this inspiring event brings together 400 community leaders, change-makers and everyday heroes for an afternoon of recognition, connection, and a delicious lunch. Come enjoy lunch and the awards ceremony at the Cocoanut Grove at the Santa Cruz Beach Boardwalk. 

May 15: Aptos Chamber Golf Scramble

The Aptos Chamber of Commerce invites you to its annual golf scramble – a golf par-tee at Seascape Golf Club. From business professionals to bagpipe lovers, you don’t want to miss this. Prizes and drinks will also be available. The day will be filled with entertainment from 1 to 7 p.m. and end with a dinner buffet.

May 16: NEXTies Awards

Hosted by Event Santa Cruz and Santa Cruz Vibes, come out to celebrate the up-and-coming change-makers of Santa Cruz County! Hosted at Woodhouse Blending & Brewing, join the party that is unlike any other awards show and get your tickets today.

May 17: Forks, Corks & Kegs Festival

Four hours of delicious food, ice-cold beer and fine wine. What more could you want? Enjoy the best bites and brews around with old friends and create new connections at this food and fun-filled festival hosted at Kaiser Permanente Arena.

LOOKOUT TRIVIA RETURNS

SAVE THE DATE: Lookout Trivia Nights returns! Bring your crew and test your knowledge as Lookout correspondent Wallace Baine brings the brain-tingling trivia back to Abbott Square this summer.

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Ashley Harmon (Holmes) (she/her) leads Lookout’s product and audience growth for Santa Cruz and soon-to-come, Eugene-Springfield. Ashley started at Lookout as director of advertising and marketing....