From sipping and sampling to dancing and discovering, Santa Cruz County’s festivals and community events keep the good times rolling. Our readers voted for their favorite community celebrations, and the 2025 Lookout List: Community & Events winners and runners-up prove that there’s always something worth showing up for. Find more Lookout List winners here.
Favorite Art Fair/ Festival
Winner: Santa Cruz Open Studios
Locals and visitors alike praise the annual Santa Cruz Open Studios for its wide variety of local artists and the rare chance to step inside their workspaces to see how art is made. Lookout List voters call the event “inspiring” and a favorite showcase of the community’s creative talent.
Runner-up: Capitola Art and Wine Festival
Favorite Drink Festival
Winner: Capitola Art & Wine Festival
The Capitola Art & Wine Festival in Capitola Village is known for its mix of artists and regional wineries, all set amid a scenic beachside backdrop. Lookout List voters say the event is lively yet casual, offering a unique combination of art, wine and community fun.
Runner-up: Scotts Valley Art Wine & Beer Festival
Lookout Staff Pick: Favorite Drink Festival – Gourmet Grazing on the Green
Gourmet Grazing on the Green is not only a drink festival with dozens of booths from local restaurants, but I love this annual fundraiser for the Santa Cruz Cancer Benefit Group. Hosted in Aptos Village Park, this event is a must-go for me. You’re able to try all of the best, most community-oriented wineries all in one fell swoop. The energy is really fun, the wine (and some beer and mixed-drink options) are fantastic, and it all goes to support a great cause.
– Ashley Harmon
Favorite Food Festival
Winner: Greek Festival
223 Church St., Santa Cruz 95060
The Greek Festival in downtown Santa Cruz stands out for its authentic Greek food and live music. Voters highlight the festival’s mix of flavorful specialties like moussaka and spanakopita and the joyful dancing as key reasons it earns its favorite‑food‑festival status.
Runner-up: Watsonville Strawberry Festival
Main St., Watsonville 95076
Favorite Street Fair/Festival
Winner: Capitola Art & Wine Festival
Lookout List voters say the Capitola Art & Wine Festival – which typically happens in September – is a favorite street fair for its lively beachfront setting and selection of art and wine vendors. Attendees appreciate the mix of local artists, regional wineries, and family-friendly activities that make the event a must-visit each year.
Favorite Music Festival
Winner: Cabrillo Festival of Contemporary Music
307 Church St., Santa Cruz 95060
Music-lovers praise the annual Cabrillo Festival of Contemporary Music at the Civic Auditorium in downtown Santa Cruz for its world-class musicians. Voters highlight the festival’s creative, cutting-edge programming with “mind-blowing and mind-bending performances.”
Runner-up: Redwood Mountain Fair
5401 Graham Hill Rd., Felton 95018
Favorite Local Maker Pop-Up Event
Winner: Collective Santa Cruz – Extra Tasty Tour
Readers say the Extra Tasty Tour by Collective Santa Cruz is a must‑go local maker pop‑up event because all the vendors lean into the monthly theme – sweet, sour, salty, bitter or umami – and create special offerings available only at the event. Fans highlight the down‑to‑earth vendors, family‑friendly activities and the wide range of creative makers sharing jewelry, ceramics, sweets, drinks and more.
Runner-up: Midtown Fridays
1111 Soquel Ave., Santa Cruz 95062
Favorite Stop on a First Friday Santa Cruz Art Tour
Winner: Tannery Arts Center
1010 River St., Santa Cruz 95060
Lookout List voters say this monthly stop on the First Friday Art Tour stands out because it offers a variety of open studios and gallery experiences. Art lovers enjoy wandering the grounds, exploring working artists’ spaces, outdoor artwork and galleries.
Runner-up: M.K. Contemporary Art
703 Front St., Santa Cruz 95060
Favorite Stop on the Open Studios Art Tour (South County)
Winner: Cristina Sayers
2200 Wallace Ave., Aptos 95003
Lookout List voters say Cristina Sayers is a standout stop on the South County Open Studios Art Tour for her engaging studio experience, appreciating “her energy and color.” Visitors highlight the opportunity to see her creative process up close and take home one-of-a-kind pieces that capture the spirit of the community.
Runner-up: John McKinley
217 Coronado Dr., Aptos 95003
Favorite Stop on the Open Studios Art Tour (North County)
Winner: Tannery Arts Center
1010 River St., Santa Cruz 95060
Lookout List voters say the Tannery Arts Center is a favorite stop on the North County Open Studios Art Tour for its combination of open studios and gallery exhibitions. Visitors enjoy exploring the working artists’ living/studio spaces, discovering unique artwork and engaging directly with creators in a vibrant, community-focused setting.
Runner-up: Chris Johnson Glass – Studio Zayante
131 Old Coast Rd., Davenport 95017
Lookout Staff Pick: Favorite Stop on the Open Studios Art Tour – Eckerman Studios
Eckerman Studios isn’t just where a family of artists creates, it’s also a home and a work of art itself. Working from their Seabright property, a father, son and daughter specialize in rockwork, dog sculptures, paintings and mixed-media prints. The space is covered in driftwood sculptures, whimsical paintings, linocut prints and a range of rock art items, like archways, large dogs and lamps.
– Hillary Ojeda
Favorite Nonprofit Awards Event
Winner: Volunteer Center of Santa Cruz County “Be The Difference” Awards
The annual Be The Difference Awards, presented by the Volunteer Center of Santa Cruz County, honors everyday people and businesses working to improve the community. Attendees love that the event gives these local heroes well-deserved recognition on stage, complemented by engaging video summaries that highlight their impact.
Lookout Staff Pick: Favorite Non-Profit Awards Event – Pajaro Valley Chamber Awards Dinner
One of the best perks of my role as Marketing Partnerships Representative at Lookout is attending community events year-round, and the Pajaro Valley Chamber of Commerce Awards Dinner has become a personal favorite. Shaz Roth and her team, along with event emcee and voice of the Santa Cruz County Fair, Ron Haedicke, consistently deliver one of the most vibrant Chamber events of the year, complete with a fantastic catered dinner and Gizdich Ranch pie dessert, local wine, a lively auction, and great conversation with community members from all walks of life. This year’s honorees included Laura Owens, Jess Brown, D’La Colmena Market, Sons & Daughters of Italy, the Salvation Army Back Pack Drive, and Bob & Linda Erbe – a true celebration of the diverse community that makes our county thrive.
– Duffy Barrett
Favorite Nonprofit Fundraiser
Winner: Teen Kitchen Project – Everett Farm Fundraiser
2111 Soquel San Jose Rd., Soquel 95073
Voters say the annual Everett Farm fundraiser by Teen Kitchen Project draws praise for blending top‑tier local cuisine and a mission‑driven event that supports teens and meal deliveries in Santa Cruz County. Reviewers highlight the special multi‑course menus, community‑rich atmosphere and the fact that every dollar raised directly backs healthy meals for families in need.
Runner-up: Santa Cruz County Animal Shelter: St. Pittie’s Party
1001 Rodriguez St., Santa Cruz 95062
Favorite Place to Volunteer
Winner: Santa Cruz County Animal Shelter
1001 Rodriguez St., Santa Cruz 95062
580 Airport Blvd., Freedom 95019
Volunteers say the Santa Cruz County Animal Shelter is a welcoming place where adults and teens alike can make a meaningful difference by walking dogs, brushing cats or even helping with outdoor and event tasks. They highlight the accessible, organized entry process – minors may volunteer starting at age 12 with an adult – and the deep sense of reward from helping animals in need.
Runner-up: Second Harvest Food Bank Santa Cruz
800 Ohlone Parkway, Watsonville 95076
