As summer winds down and Santa Cruz heads into a busy fall, Lookout is hitting the community calendar with events that inform, inspire and connect. From Labor Day gatherings to back-to-school happenings, September is full of moments that bring our county together. Here’s a look at 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. 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!
HIGHLIGHTED EVENTS:
Lookout Trivia Night | September 3
Put your knowledge to the test at Lookout’s summer trivia series. Hosted by Wallace Baine, our monthly event at Abbott Square runs the first Wednesday of each month from 6:30 to 8 p.m. Bring your brainy friends and the know-it-alls in your life for a fun, fast-paced evening of competition.
Film Screening: Stripped for Parts: American Journalism on the Brink | September 24
Join Lookout Santa Cruz and CalMatters for a powerful night at the movies. This gripping documentary exposes the corporate dismantling of local news and what’s at stake for democracy when watchdog journalism disappears. The evening at the Del Mar Theatre includes a screening and a panel discussion on the state of journalism and what’s next for Santa Cruz and California.
Save the date: Lookout Extra Tasty Tour with Lily Belli — Salty | Saturday, September 27 Details coming soon!
MORE EVENTS:
Santa Cruz County Fair | September 11–15
Nothing says September in Santa Cruz County like the fair! From carnival rides and live music to 4-H exhibits, livestock shows and endless fair food, the annual Santa Cruz County Fair brings together the best of local tradition and community spirit. Head to the Watsonville Fairgrounds to experience five days of family fun, local culture and plenty of fried treats.
Capitola Art & Wine Festival | September 14–15
Sip, stroll and soak up the best of Capitola! The Art & Wine Festival returns with more than 100 fine artists, nearly 20 Santa Cruz Mountain wineries, delicious local food and live music throughout the village. Add in a kids’ art area and ocean views, and you’ve got the perfect late-summer weekend.
Farm Discovery “Thrive” Fall Feast | September 21
Gather under the harvest moon for an unforgettable evening on the farm! Farm Discovery’s annual Fall Feast pairs a locally sourced, chef-prepared meal with fine wines, live music and the beauty of Live Earth Farm. All proceeds support Farm Discovery’s hands-on education programs for local kids.
Extra Tasty Salty Festival | September 27
Get ready to savor the flavor at the fifth stop on Collective Santa Cruz’s Extra Tasty Tour at Humble Sea. After exploring sweet, bitter, sour, and umami, September’s Salty event celebrates the tastes that make our favorite foods pop. Come taste, discover, and connect with local makers bringing bold, briny flavors to life. Free to attend. Stay tuned for details on a special behind-the-scenes tasting tour of the festival with Lookout’s own food and drink correspondent, Lily Belli.
Aptos Chamber Community Showcase & Artisan Market | September 28
Celebrate Aptos and all things local! This free community event features artisan vendors, live music, kids’ activities, tasty eats and plenty of opportunities to connect with neighbors and local businesses. A perfect way to spend a fall Saturday in the heart of Aptos.
MAKE SURE TO CHECK OUT:
Santa Cruz Shakespeare | Through September 20
Spend a summer evening under the redwoods at the Audrey Stanley Grove, where Santa Cruz Shakespeare presents its 2025 season, themed “No One Is Alone.” The festival blends classics and contemporary stories with music, community, and theatrical magic.