WEEKENDER
Your cheat sheet for eating well and going out in Santa Cruz County.
Sept. 17, 2026
THE FAIR, MUSIC, ART AND OUTRIGGERS
Music, art, outriggers, a fair — this weekend has it all.
The Santa Cruz County Fair began yesterday and runs through Sunday at the Santa Cruz County Fairgrounds in Watsonville. See what’s in store through the lens of Lookout photojournalist Kevin Painchaud, who captured opening day. Andy Vargas, Santana’s lead singer and a Watsonville native, will take the stage on Friday night alongside his father, Javier Vargas, a celebrated mariachi musician. Lookout’s Alia Yee Noll and Tania Ortiz previewed the performance.
Several beloved community events are converging on Saturday. Artists, live performances and community fundraising come to the Santa Cruz Mountains for the Bonny Doon Art, Wine & Brew Festival from 2 to 7 p.m. On the other side of the mountain, Ben Lomond Scottish Day returns to Ben Lomond County Park from 1 to 5 p.m. for an afternoon of live music, highland dance, sword fighting and falconry.
The 34th annual Aloha Outrigger Races will take off from the Santa Cruz Municipal Wharf starting at 9 a.m. (Mission West’s Aloha Fest at 5 p.m. in Santa Cruz would be a fun Hawaiian-themed afterparty.) At 5:30 p.m., celebrated music maker Santa Cruz Guitar Company marks half a century with a 50th-anniversary concert at the Rio Theatre. Tickets start at $50.
That’s just the topsoil. Be sure to dig into the community calendar for a full list of events happening this weekend. – Lily Belli
UPCOMING EVENTS YOU’LL LOVE
Get full access to Lookout Santa Cruz
Become a member to read all of Lookout’s local coverage, from politics and policy to education, dining and more. Annual and monthly membership options are available — start reading for as little as $17 today!
FROM THE LOOKOUT LIST
FAVORITE DINNER WITH A VIEW
JACK O’NEILL RESTAURANT & LOUNGE
“Great food, views out Steamer Lane and east along the Boardwalk and the coast southeast.”
ICYMI: ARTS & DINING STORIES
➤ Para leer el artículo en español, haga clic aquí.
A TREAT BEFORE YOU GO
If you’re meeting up with friends at a bar this weekend, I have some suggestions. Check out my guide to some of the best martinis in Santa Cruz County. – Lily Belli
Play the Wordrow Puzzle of the Day
Six tries to guess the word right!
Sudoku, crosswords and more word puzzles await – play new daily puzzles in the free Lookout App. Available in the Apple App Store and Google Play Store.