Weekend Guide: Things to Do in Santa Cruz & Monterey — August 1-2
This is one of those weekends that makes you remember exactly why you live here. Three major festivals, live music under the redwoods, a strawberry-themed celebration that takes over an entire downtown, and the Boardwalk humming with summer energy. Whether you have lived here your whole life or you are visiting for the first time, August 1-2 is packed with reasons to get out the door.
I have been exploring Santa Cruz County for over 50 years, and weekends like this one still feel special. Here is your guide to making the most of it.
Friday, July 31 — Kickoff
Watsonville Strawberry Festival Kickoff
5:00 PM — 9:00 PM | City Plaza Park, Watsonville
The weekend starts early with a free kickoff celebration at City Plaza Park. Live music, community booths, and a preview of the berry-filled festivities coming Saturday and Sunday. Free to attend. A great warm-up for the main event.
Free Movie on the Beach: Jurassic Park
Dusk (approx 8:30 PM) | Santa Cruz Beach Boardwalk
The Boardwalk's Free Movies on the Beach series continues Friday night with Jurassic Park. Bring a blanket or a low chair, grab some Boardwalk snacks, and watch one of the greatest blockbusters ever on a giant screen with the sound of the surf behind you. Free.
Aloha Music & Arts Festival — Day 1
Noon — 6:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Ave, Watsonville
The inaugural Aloha Music & Arts Festival kicks off Friday with Polynesian cultural performances, live music, hula dancing, arts and crafts, and Island-inspired food. Free admission. Parking $20. A brand-new family-friendly tradition in Watsonville.
Saturday, August 1
Westside Santa Cruz Farmers Market
9:00 AM — 1:00 PM | Corner of Highway 1 and Western Drive, Santa Cruz
The year-round classic. Summer produce is at its peak: heirloom tomatoes, peaches, corn, berries, and flowers. Grab a coffee, walk the stalls, and load up on everything you need for a picnic at the festival later. A Saturday morning ritual for good reason.
Aptos Farmers Market
8:00 AM — 12:00 PM | Cabrillo College, 6500 Soquel Drive, Aptos
The Aptos market is a quieter, more laid-back alternative with the same incredible local produce. Live music, local honey, artisan breads, and prepared foods. Pick up a pastry and enjoy the morning.
Scotts Valley Farmers Market
8:00 AM — Noon | 219 Mt. Hermon Road / Graham Plaza, Scotts Valley
Another Saturday option. Scotts Valley's market runs through November with seasonal produce, crafts, and a friendly small-town vibe.
Aloha Music & Arts Festival — Day 2
Noon — 6:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Ave, Watsonville
Day two of this free Polynesian cultural festival. Hula performances, live Island music, arts and crafts vendors, and food celebrating the flavors of the Pacific. Perfect for families. Parking $20.
Watsonville Strawberry Festival — Day 1
11:00 AM — 8:00 PM | Main Street and E. Beach Street, Downtown Watsonville
The main event. Free admission. Three stages of live entertainment, 100-plus vendors, carnival rides and games, a Strawberry Jam 1K/5K Fun Run (registration required), a strawberry costume contest, and a community mural project. The food alone is worth the trip: strawberry pizza, strawberry tacos, strawberry churros, chocolate-drizzled strawberries, strawberry shortcake, strawberry popcorn, and strawberry smoothies. Parking is available at the Civic Plaza Parking Garage (275 Main St.) and the West Beach Street Parking Garage (21 W. Beach St.). This is Watsonville at its very best.
6th Annual Santa Cruz Mountains Brewgrass Festival
Gates at 1:00 PM | Roaring Camp Railroads, 5401 Graham Hill Road, Felton
Bluegrass and craft beer under the redwoods. This year's lineup includes bluegrass legend Sam Bush, Jesse Daniel, Rainbow Girls, Crying Uncle Bluegrass Band, Dominique and the Diamonds, Deep Thicket Dwellers, and Wild Iris. Local breweries pouring their best, food trucks, and family-friendly activities throughout the day. The VIP Brewgrass Tasting Train departs at noon from the Santa Cruz Beach Boardwalk and rolls through the forest to Roaring Camp with exclusive beer tastings and live music onboard. Tickets and details at scmbrewgrassfest.com. This is my personal pick for the weekend.
Church Street Fair
Saturday & Sunday | Church Street, Santa Cruz (adjacent to the Civic)
Running alongside the Cabrillo Festival of Contemporary Music, the Church Street Fair features local artisans, outdoor live performances, wine and craft beer, and festival food. A lovely, artsy stroll between the Civic and Abbott Square. Free to browse.
Cabrillo Festival of Contemporary Music
7:00 PM | Santa Cruz Civic Auditorium, 307 Church Street, Santa Cruz
The Cabrillo Festival continues its summer run with a concert at the Civic. This festival has been pushing musical boundaries since 1963 and draws world-class composers and performers. Tickets at cabrillomusic.org.
Eilen Jewell at Kuumbwa Jazz
7:00 PM | Kuumbwa Jazz Center, 320-2 Cedar Street, Santa Cruz
Americana and folk singer-songwriter Eilen Jewell brings her intimate, storytelling style to Kuumbwa. An intimate show in one of Santa Cruz's best listening rooms.
Eric Lindell & The Westside Summer League at Moe's Alley
Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Roots rock and blues from a New Orleans-born artist who blends soul, swamp pop, and rock into an irresistible groove. Moe's Alley stays one of the best places to catch live music in the county.
Free DJ Dance Party on the Beach
8:30 PM — 9:30 PM | Boardwalk Colonnade, Santa Cruz
Part of the Evenings on the Colonnade series. The Santa Cruz DJ Company keeps the beach moving every Saturday and Sunday night through August 6. Dancing under the stars with the waves rolling in. Free and open to all ages.
Looff Carousel 115th Anniversary Celebration
All day | Santa Cruz Beach Boardwalk, 400 Beach Street
August 1 marks the start of a month-long celebration of the Boardwalk's historic 1911 Looff Carousel, a National Historic Landmark. Throwback ride pricing, a chance to catch the coveted Golden Ring, and a call to share your carousel memories on social media. One of only a handful of hand-carved, triple-row carousels still operating. A ride on these wooden horses connects you to over a century of Santa Cruz summer memories.
Sunday, August 2
Live Oak / Eastside Farmers Market
9:00 AM — 1:00 PM | 15th Avenue and East Cliff Drive, Santa Cruz
Sunday is farmers market day on the east side. A neighborhood-friendly market with local produce, artisan vendors, and a relaxed pace. Grab your market haul and head down to the nearby beach for a Sunday picnic.
Watsonville Strawberry Festival — Day 2
11:00 AM — 7:00 PM | Main Street and E. Beach Street, Downtown Watsonville
If you missed Saturday, Sunday is your last chance. Same incredible food, same carnival fun, same live entertainment. The strawberry costume contest is a highlight and the mural project wraps up. Go. Eat a chocolate-drizzled strawberry for me.
Church Street Fair — Day 2
Sunday hours | Church Street, Santa Cruz
A second day to browse artisan booths, enjoy outdoor music, and soak in the artsy downtown atmosphere.
The Trolley Drops — 1st Sundays
Time TBD | Santa Cruz Civic Auditorium, 307 Church Street, Santa Cruz
A free community event on First Sundays featuring local music, vendors, and family activities. Check the Civic website for this month's lineup.
Free DJ Dance Party on the Beach
8:30 PM — 9:30 PM | Boardwalk Colonnade, Santa Cruz
Sunday edition. If you missed Saturday, here is your second chance to dance with your feet in the sand. Free.
All Weekend: Outdoor Adventures
Kayaking Elkhorn Slough
Daily | Moss Landing (about 20 minutes south of Santa Cruz)
One of the best wildlife kayaking spots in California. Sea otters, harbor seals, and hundreds of bird species. Kayak Connection and Monterey Bay Kayaks both offer rentals and guided tours. The slough is protected and calm, perfect for beginners.
Surfing at Cowell's Beach
Daily | Cowell's Beach, Santa Cruz
Gentle waves, sandy bottom, and a dozen surf schools ready to help you catch your first wave. Club Ed, Adventure Out, and Surf School Santa Cruz all offer lessons with gear included. Summer is prime learning season.
Hiking Henry Cowell Redwoods State Park
Daily | 101 N Big Trees Park Road, Felton
The old-growth redwood loop trail is an easy 0.8-mile walk through towering giants that have stood for centuries. Henry Cowell is right next to Roaring Camp, so you can pair a morning hike with the Brewgrass Festival in the afternoon.
Monterey Bay Aquarium
Open daily, 10:00 AM — 5:00 PM (Sat-Sun 9:00 AM — 5:00 PM) | 886 Cannery Row, Monterey
A world-class attraction that is a short drive down the coast. The Kelp Forest, Open Sea exhibit, and the always-mesmerizing jellyfish gallery. Summer weekends sell out, so book ahead online.
Evenings on the Colonnade
8:30 PM — 9:30 PM nightly (through August 6) | Boardwalk Colonnade Deck, Santa Cruz
Live entertainment every summer night at the Boardwalk. Saturday and Sunday feature the DJ Dance Party. Monday through Thursday bring different acts: juggling, magic, live music. All free. The perfect way to end any summer evening.
Food & Drink Highlights
Brewgrass Festival Craft Beer
Local breweries pour their best seasonal brews at the Brewgrass Festival in Felton. From hoppy IPAs to rich stouts, the beer garden under the redwoods is a highlight of the festival.
Strawberry Everything in Watsonville
The Watsonville Strawberry Festival is a food lover's paradise. Strawberry pizza (yes, really), strawberry tacos, chocolate-drizzled berries, fresh strawberry shortcake, strawberry churros, strawberry popcorn, and strawberry smoothies. Plus classic festival fare from 100-plus vendors.
Downtown Santa Cruz Food Trucks
North end of Pacific Avenue, between Locust and Water Streets
The Downtown Santa Cruz Food Truck Summer Series runs through October with rotating trucks, live music, and a street-fair atmosphere. Check downtownsantacruz.com for this weekend's lineup. Drunk Monkey and other local favorites rotate through.
New Openings Worth Checking Out
Downtown Santa Cruz is buzzing with new spots. Mane Kitchen & Cocktails (1222 Pacific Avenue) is a fine dining addition from Chef Desmond Schneider. The Alley Oop Cocktail Bar opened downtown early this year. Luna's Borikén Bites is now serving Puerto Rican dishes at Abbott Square Market (725 Front Street), and India Gourmet, the longtime farmers market favorite, has a permanent kiosk there too. And The Cruz Room is coming soon to 1520 Mission Street. Lots of reasons to explore downtown right now.
Notable Community News
Bliss Boutique Closes in Monterey. After 25 years, Bliss Boutique at 380 Alvarado Street in downtown Monterey is closing. Their final sale runs this weekend with fixtures and displays for sale. A reminder to support our local shops while we have them.
Monterey Car Week is Coming. While it is quiet on the Monterey Peninsula this weekend, get ready for Monterey Car Week (August 7-16). This is one of the biggest automotive events in the world and it transforms the entire Peninsula. Start planning now.
Capitola Art & Wine Festival. Mark your calendar for September 12-13. The Capitola Art & Wine Festival returns to the Village with wine tasting, local artists, and live music. Free admission. Wine tasting glasses available for $20.
Shareable Social Captions
Planning to post about your weekend? Here are some ready-to-copy captions for Instagram and Facebook, written as if I am sharing my own weekend plans with friends.
This weekend is going to be epic. Saturday: Brewgrass Festival under the redwoods in Felton (Sam Bush, craft beer, VIP train from the Boardwalk). Sunday: Watsonville Strawberry Festival for chocolate-dipped berries and carnival rides. Who else is going big this weekend? 🌴 🍋 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #BrewgrassFestival
Three festivals in one weekend. Brewgrass in Felton, Strawberry Festival in Watsonville, and the brand-new Aloha Music & Arts Festival at the Fairgrounds. That is a Santa Cruz summer, right there. Plus farmers markets, Boardwalk carousel anniversary, and free movies on the beach. See you out there. 🌊 🌲 #SantaCruzEvents #WeekendVibes #ThingsToDoSantaCruz #CaliforniaSummer #SantaCruzLife
Family-friendly alert. The Aloha Music & Arts Festival (free!) and the Watsonville Strawberry Festival (also free!) are both incredibly fun for kids. Hula dancing, carnival rides, strawberry pizza, and a community mural project. Pack the crew and make a day of it. 🦊 🍋 #FamilyFunSantaCruz #SantaCruzEvents #WeekendInSantaCruz #SantaCruzLife #MontereyBay
My Saturday plans. Start at the Westside Farmers Market for peaches and flowers. Head to the Brewgrass Festival for bluegrass and cold beer under the redwoods. End the night dancing on the Boardwalk beach. This is exactly what summer in Santa Cruz is about. 🟡 🦶 #WeekendInSantaCruz #SantaCruzEvents #ThingsToDoSantaCruz #SantaCruzLife #CaliforniaSummer
Did someone say strawberry pizza? The Watsonville Strawberry Festival has strawberry everything and I am here for it. 100-plus vendors, live music, carnival rides, and the best berry in the county. Two days, free admission, all the flavor. See you downtown. 🍋 🎉 #WatsonvilleStrawberryFestival #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife
Enjoy the weekend, everyone. Whether you are dancing at the Boardwalk, hiking the redwoods, or eating your way through Watsonville, I hope this weekend gives you exactly what you need. If you are thinking about buying or selling a home in Santa Cruz or Monterey County, or if you have questions about what this market looks like for your situation, I would love to hear from you. Call me at (831) 247-5719 or visit the contact page. I want you to make informed decisions, and I love helping people find their place in this beautiful corner of California.
Talk soon.
Kieron Bery, REALTOR® — Century 21 Masters
More from Kieron Bery: Neighborhood guides | Client reviews | Summer living in Santa Cruz County | July 2026 market update | About Kieron