We’re a digital local newspaper, but we are a part of the physical community every day, and there’s a lot happening in Santa Cruz County. Here’s the sampling of upcoming events hosted by Lookout and our partners you may enjoy.
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, duffy@lookoutlocal.com.
See you out and about.
HIGHLIGHTED EVENTS:
Lookout Santa Cruz Trivia Night Hosted by Wallace Baine – Wed. June 4, 6:30-8pm
Looking for a way to kick off summer fun? Trivia nights will be returning the first Wednesday of every month this summer, starting next week. Challenge your memory in a friendly competition and strengthen your trivia skills. Bring your friends that randomly share funky facts with you and the know-it-alls! Lookout’s very own Wallace Baine will be hosting this special summer series at Abbott Square.
Extra Tasty Tour – ‘Bitter’ June 28
The Extra Tasty Tour, hosted by The Collective, will be kicking off their next event on Saturday, June 28th. Each Extra Tasty Tour event is centered around five flavors: sweet, salty, bitter, sour and umami. June’s theme of the month is bitter, complete with coffee, chocolate and heavy craft beer features. Previously events have been ticketed. However, this year, each event entry is free. Join for entertainment, music and extra tasty treats.
MORE EVENTS TO CHECK OUT:
National Trails Day – Saturday, June 7
Santa Cruz Mountains Trail Stewardship’s biggest event of the year is near. Happening next Saturday, June 7, this is the third annual National Trails Day celebration! Calling all nature lovers and hike enthusiasts, the event starts at 9 a.m. and ends at 5 p.m. You can expect live music, friendly vibes, prizes, food, and a huge afterparty. These are just some of the activities of this special day and a great way to connect to the land. From beginner sites and first-timers at the trash cleanup in Pogonip to moderately difficult sites for earth lovers who like a challenge, there are different types of trail work to choose from.
Capitola Art & Wine Kick Off Party – Sunday, June 8
The 2025 Capitola Art & Wine Festival invites you to their Secret Garden Soiree at Bargetto Winery. Appreciate a delightful spring afternoon along Soquel Creek from 2 p.m. to 5 p.m. on Sunday, June 8. This is a fundraiser hosted by the Capitola-Soquel Chamber of Commerce to support the 42nd annual Capitola Art & Wine Festival. Enjoy wine tasting from wineries that will be at the festival in September.
Munch on tasty appetizers as silently as possible during the silent auction, with donations from Festival artists and local businesses. Tickets are $75, make sure to register before they sell out!
Thursday, June 12 – Rather Awards
Community Health Trust of Pajaro Valley is a non-profit organization focused on health equality for all individuals. The Rather Awards celebrates those who uplift the lives of people in Pajaro Valley. Proceeds benefit the Phil Rather Memorial Endowment Fund, which supports the Diabetes Health Center. Let’s honor the awardees and their hard work on Thursday, June 12 at the Seascape Golf Club. Happy hour is from 4:30 p.m. to 5:30 p.m., followed by the awards ceremony until 7:30 p.m.
Santa Cruz Juneteenth – Saturday, June 14
Don’t miss out on Santa Cruz Juneteenth, Saturday at Laurel Park. From 12 p.m. to 5 p.m., the London Nelson Community Center is organizing this event to celebrate African American heritage. Juneteenth is a free event for the Black community and its allies. The theme this year is Body, Mind and Soul. Spread the word and enjoy countless activities, craft booths, mouthwatering soul food and a number of performances.
Beginning at 11:30 a.m., create an Ancestors Altar. The Second Line Sidewalk Parade begins at City Hall at 12 p.m. Afterward from 1 p.m. to 2 p.m. at Laurel Park, there will be a basketball skills contest and clinic.
18th Annual Capitola Rod & Custom Classic Car Show – Saturday, June 14
The 18th Annual Capitola Classic Car Show will be held along the coastline, starting at the Santa Cruz Boardwalk to Capitola. Cruise on over to the show on Saturday, June 14, starting at 8:30 a.m. Make the most out of your weekend with gorgeous automobiles, music, and family-friendly fun at the beach. From vintage car lovers to muscle cars, visit and stop by for vendor booths, a raffle, trophies and more.
Sip for Second Harvest Food Bank – Sunday, June 22
Second Harvest Food Bank is hosting Sip for Second Harvest on Sunday, June 22nd. Try local wines and relish appetizers at Seascape Beach Resort. Event tickets must be purchased before the event, but raffle tickets are available for purchase at the event. All proceeds from this event benefit the Second Harvest Food Bank, which is dedicated to providing healthy food and nutritional education to our community. Entry costs $75 and VIP SIP tickets are $125, complete with a swag bag, champagne and more.
10th Annual Farm to Fork Gala – Saturday, June 28
The 10th Annual Farm to Fork Gala commemorates Community Bridges’ mission to deliver vital resources across Santa Cruz County and Monterey Bay Area. Funds from this event directly impact the lives of more than 20,000 local children and families. A locally sourced seasonal gourmet menu will be provided, along with an energetic live silent auction. Celebrate these incredible achievements and donate to an important cause on Saturday, June 28 at the Seascape Golf Club.
