May is underway, election season is in full swing, and as springtime begins to close, Lookout’s calendar of events is focused on soaking up the sun and beauty of Santa Cruz County and its residents. Lookout is hosting election events, including another candidate forum to help keep the county informed politically. From art markets to golfing events, May is sure to be a month full of excitement and fun activities. Below are upcoming events hosted by Lookout and our partners. 

We’re proud to partner with local organizations to highlight events that reflect the heart of Santa Cruz County. It’s all part of our mission to make local news a living, breathing part of community life.

And we couldn’t do it without our Marketing Partners, who help us spotlight key happenings across the county. Interested in joining our Media Sponsorship program? Contact Duffy Barrett at duffy@lookoutlocal.com.

See you out in the community this month!


Join Lookout Santa Cruz to hear from mayoral and Santa Cruz City Council candidates in the leadup to this year’s primary election. Moderated by Lookout Santa Cruz’s Community Voices opinion editor, Jody K. Biehl, candidates will be asked questions, answering on the spot. Community members will get the opportunity to raise issues they are curious and passionate about during an audience questions section of the debate. This event will take place at Hotel Paradox from 5:30 to 8 p.m. and is open to all community members for free.


Hwy17 Studios is hosting a one-night-only live interview and performance with Kat Moss, lead singer of Scowl, featuring local artists. The event will begin at 6 p.m. with a live on-stage conversation with an intermission that will be followed by a set by Kat, local musicians and a special guest with collaborative songs. 

Make sure to secure your tickets for Canadian indie pop band Peach Pit. The group will be playing at the Quarry Amphitheater beginning at 8 p.m. 

Explore the Spring Art Market at the Tannery Arts Center from 10 a.m. to 5 p.m. This event is free and open to the public, with live music performances from La Otra Banda and Yellowcat. Enjoy the local fine art, textiles, ceramics and jewelry while connecting with artists from around the county. 

Celebrate Mother’s Day meaningfully this year by participating in the Pajaro Valley Shelter Services’ 42nd annual Mother’s Day Walk and Run. This event takes place on a scenic 10K/5K/1K trail to benefit families experiencing homelessness. Participants are invited to take the event at whatever pace fits them. Reservations can be made online up until 7 a.m. the day of the race. Help make this race a milestone of compassion, caring and community!

Tee up alongside local golfers at Seascape Golf Club from 1 to 7 p.m. Whether you attend as a golfer, hole sponsor or event sponsor, this event is sure to be fun and a great networking opportunity. 

Mountain Community Theater is proud to present its opening of what is widely considered one of America’s best plays, “Who’s Afraid of Virginia Woolf? An original Broadway production that has won five Tonys and was nominated for 13 and won five Academy Awards, it explores the marriage of a couple George and Martha over the course of a night of fun and games involving a young couple with secrets of their own. This play is full of mystery, wit and dark comedy. 

Downtown Watsonville will host the seventh annual Watsonville Wine, Beer and Art Walk from 1 to 5 p.m. Eventgoers will receive a sampling souvenir cup and passport including downtown locations to explore different tastings at each site. Explore local wines, craft beers and artwork by local artists while strolling through downtown. Because this event is so popular and sells out annually, make sure to secure your tickets as soon as possible.

Join the BirchBark Foundation at Chaminade Resort and Spa from 10:30 a.m. to 1:30 p.m. for an elegant brunch supporting the organization’s programs. The event will include a champagne welcome, silent auction, buffet brunch and a program that will highlight the work that BirchBark does in Santa Cruz County. Help to reduce financial barriers to veterinary care and support families and animals through difficult times.

Volunteer Center – Be The Difference Awards | May 20

Join civic and community leaders of Santa Cruz County at this year’s Be The Difference Awards gala. Hosted by the Volunteer Center, the event will take place at the Beach Boardwalk Grove from 11:30 a.m. to 1:30 p.m. Honor the 50 featured individuals, organizations and groups who strengthen the county through volunteerism.

The Aptos Chamber will hold a luncheon with Susan True from the Community Foundation of Santa Cruz County. Hosted at the Seacliff Inn, the event will take place from 11:30 a.m. to 1 p.m.

The Santa Cruz Area Chamber of Commerce is happy to host a business after-hours networking event from 5 to 7 p.m. at West Coast Community Bank’s River Street branch. Bringing together local professionals interested in building lasting relationships, creating a more connected community and supporting the economy of the county. Register for the event to experience an evening full of refreshments, connection and fostering community prosperity. 

Celebrating 15 years at Roaring Camp in Felton, the Redwood Mountain Faire is a weekend full of fun and excitement. The weekend affair will feature music all day on the Meadow and Creekside stages. With activities for all ages, the event includes bouncy houses, face painting, food, local arts and crafts, train rides and more.

Galicia Stack Lozano is a student at UC Santa Cruz and an intern at Lookout Santa Cruz through the Humanities EXCEL program led by the UC Santa Cruz Humanities Division with strategic support from The Humanities Institute