Weekend Guide: Things to Do in Santa Cruz & Monterey

This weekend is one of those rare ones where both counties are absolutely buzzing. We have the second annual Santa Cruz Jug Band Festival taking over downtown for four days, Monterey Car Week kicking off on Alvarado Street, the Cabrillo Festival of Contemporary Music presenting world premieres at the Civic, and so many farmers markets you could stock your kitchen for the month. I have lived in Santa Cruz County for over 50 years, and weekends like this remind me why I have never wanted to be anywhere else.

Here is your verified weekend guide, organized by day, with events I have confirmed through local sources. Let's get into it.

Wednesday, August 5 — Kick Off Early

Capitola Twilight Concert: The Joint Chiefs

6:00 PM — 8:00 PM | Esplanade Park Bandstand, Capitola Village
R&B, soul, and funk from The Joint Chiefs at Capitola's free Wednesday concert series. Grab takeout from one of the Capitola Village restaurants, spread a blanket on the lawn at Esplanade Park, and let the music roll in with the ocean breeze. This is the Capitola summer experience at its best. Free, all ages, and the sunset views are worth it alone.

Downtown Santa Cruz Farmers Market

1:00 PM — 5:00 PM | Cedar Street & Church Street, Downtown Santa Cruz
Wednesday is farmers market day downtown. August produce is at its peak: heirloom tomatoes, sweet corn, stone fruit, sunflowers, and fresh herbs. Grab a midweek haul and set yourself up for the weekend.

Thursday, August 6 — Jug Band Festival Opens

Second Annual Santa Cruz Jug Band Festival — Opening Night

5:45 PM — 7:30 PM | Pono Hawaiian Grill, 120 Union Street, Santa Cruz
The four-day Jug Band Festival kicks off with an intimate evening concert at Pono Hawaiian Grill. Expect washboard rhythms, kazoo solos, and the kind of joyful, homespun music that makes you smile before you even realize it. This is the second year of the festival, and it is already becoming a Santa Cruz tradition. Free.

Friday, August 7

Santa Cruz Jug Band Festival — Day 2 at the MAH

6:00 PM — 9:00 PM | Museum of Art & History, 725 Front Street, Santa Cruz
The festival moves to the MAH on Friday night with an evening of jug band music. The Rivertown Skifflers, Quake City Jug Band, and more take the stage. The MAH courtyard is a beautiful setting for this kind of acoustic fun. Free.

Midtown Fridays Summer Block Party

5:00 PM — 8:30 PM | Midtown Square, 1111 Soquel Avenue, Santa Cruz
Midtown Fridays is back with live music, rotating food trucks, local vendors, and a family-friendly block party atmosphere. This week features live music from a rotating lineup. Free admission. Grab dinner from the food trucks, browse the vendor stalls, and soak in the community energy.

Free Movie on the Beach: The Goonies

Dusk (approx. 8:30 PM) | Santa Cruz Beach Boardwalk Main Beach
The final Free Movie on the Beach of the season. The Goonies on a giant screen with the sound of the surf behind you. Bring a blanket and a jacket. This is the last one, so do not miss it. Free.

Monterey Car Week Kickoff Cruise-In

5:00 PM — 7:00 PM | 300 Block of Alvarado Street, Downtown Monterey
Car Week officially begins with a free outdoor classic-car show right on Alvarado Street. Over 30 historic race cars on display, drivers in attendance, and the whole block transforms into an open-air automotive gallery. Live music, family-friendly, and completely free. If you have never experienced Monterey Car Week, this is the easiest and most welcoming entry point. About a third of all Car Week events are free to the public.

Saturday, August 8

Jug Band Festival Main Day at Abbott Square

12:00 PM — 9:00 PM | Abbott Square Market, 118 Cooper Street, Santa Cruz
The full festival experience. Live jug bands all day, sing-alongs, homemade instrument demonstrations, and the best people-watching in downtown Santa Cruz. Performers include The Rivertown Skifflers, The Trolley Drops, Quake City Jug Band, and Washboard Rhythm Co. Grab lunch or dinner from one of the Abbott Square food vendors and stay for the whole day. Free.

Westside Santa Cruz Farmers Market

9:00 AM — 1:00 PM | Mission Street Extension & Western Drive, Santa Cruz
The Saturday ritual. 100% certified organic produce, artisan foods, live music, and a community atmosphere that has held this market together for over 15 years. August means peak-season heirloom tomatoes, corn, peaches, and enough flowers to fill your whole house.

Aptos Farmers Market at Cabrillo College

8:00 AM — 12:00 PM | 6500 Soquel Drive, Aptos
Voted "America's Favorite Farmers Market in California" three years running. Over 90 vendors offering certified organic produce, pastured meats, artisan cheeses, raw milk, fresh pasta, olive oils, and the Farmers Market String Band playing bluegrass in the background. Worth the drive for the selection alone.

Scotts Valley Farmers Market

8:00 AM — 12:00 PM | 219 Mt. Hermon Road, Graham Plaza, Scotts Valley
A smaller, friendly market with local produce, crafts, and a small-town Saturday morning feel. Perfect if you are up in the San Lorenzo Valley and want to grab your weekend groceries.

Cabrillo Festival of Contemporary Music: Youth Ensemble Concert

3:30 PM | Santa Cruz Civic Auditorium, 307 Church Street, Santa Cruz
A free chamber concert of original works programmed, produced, and performed by musicians ages 16-24 in the festival's Youth Ensemble Program. This is where you hear the next generation of contemporary composers and performers. Free.

Cabrillo Festival: CONTROL

7:00 PM | Santa Cruz Civic Auditorium, 307 Church Street, Santa Cruz
The mainstage event. Music Director Cristian Mâcelaru conducts a program exploring power, technology, and agency. The highlight is Clarice Assad's Kontrol — a festival commission and world premiere blending multimedia projections, narration, solo violin with Philippe Quint, and full orchestra. Also on the program: Jackson A. Waters's Defending Greenwood (West Coast premiere), Hannah Ishizaki's Spin (West Coast premiere), and Dan Dediu's Concerto for Orchestra (U.S. premiere). Tickets $26-$96.

Los Lobos & Los Lonely Boys at the Golden State Theatre

8:00 PM | Golden State Theatre, 417 Alvarado Street, Monterey
The Brotherhood Tour brings Los Lobos and Los Lonely Boys to Monterey's most beautiful historic theatre. Latin rock, Texas blues, and decades of musicianship on one stage. If you are in Monterey for Car Week, this is your Saturday evening plan. Tickets $65-$153 at goldenstatetheatre.com.

Monterey Pre-Reunion & Corkscrew Hillclimb

Gates open 7:00 AM | WeatherTech Raceway Laguna Seca, 1021 Monterey Salinas Highway, Salinas
Historic race cars hit the track for two full days of competition. Saturday features practice and qualifying sessions, plus the fan-favorite Corkscrew Hillclimb on Sunday where drivers race up the legendary 18-story drop in 450 feet. Vintage Formula 1, Trans-Am muscle, and classic sports racers. Tickets at laguna-seca.com.

Sunday, August 9

Tri Santa Cruz

First wave 8:00 AM | Cowell Beach / Depot Park, Santa Cruz
Sprint and Olympic-distance triathlon, plus aquabike, duathlon, and aquathlon categories. International (Olympic) distance starts at 8:00 AM, Sprint at 8:30 AM, with family-friendly super sprint waves at 8:45 AM. The swim is a sheltered ocean course off Cowell Beach, the bike winds through Santa Cruz's coastal neighborhoods, and the run follows West Cliff Drive with unbeatable ocean views. Great spectator sport with the Boardwalk and Main Beach as the backdrop. Free to watch.

Jug Band Festival — Final Day

Times and venue vary | Downtown Santa Cruz
The festival wraps up Sunday with more live jug band music. Check the festival schedule at Abbott Square Market or santacruz.org for the day's specific lineup and venues. Free.

Live Oak / Eastside Farmers Market

9:00 AM — 1:00 PM | 15th Avenue & East Cliff Drive, Santa Cruz
Sunday is farmers market day on the east side. A relaxed, neighborhood-friendly market with local produce, artisan foods, and a great location just steps from the beach. Grab your market haul and walk down to the sand.

Cabrillo Festival: HOPE AS OUR BANNER — Grand Finale

7:00 PM | Santa Cruz Civic Auditorium, 307 Church Street, Santa Cruz
The 64th season of the Cabrillo Festival closes with a powerful program conducted by Cristian Mâcelaru. World and West Coast premieres including Eunike Tanzil's Ascending Creatures, Lisa Bielawa's Pulse (featuring violinist Tessa Lark), and Elena Kats-Chernin's Rainbow Promise (U.S. premiere), plus a new poem by Rita Dove. This is the grand finale of three weeks of boundary-pushing music. Tickets at cabrillomusic.org.

Monterey Pre-Reunion & Corkscrew Hillclimb — Day 2

Gates open 7:00 AM | WeatherTech Raceway Laguna Seca
Sunday is the main spectator day with the Fourth Annual Corkscrew Hillclimb. Race cars charge up the track's most iconic feature. Full day of on-track action across multiple race groups. A perfect day trip from Santa Cruz.

Del Monte Center Farmers Market

8:00 AM — 12:00 PM | Del Monte Shopping Center, 1410 Del Monte Center, Monterey
Over 60 vendors at the Sunday market in Monterey. If you are down for Car Week, swing by on your way home. Local produce, artisan foods, and a lively parking lot market atmosphere.

All Weekend: Outdoor Adventures

Kayaking Elkhorn Slough

Daily | Moss Landing (about 20 minutes south of Santa Cruz)
August is spectacular on the slough. Sea otters floating on their backs, harbor seals hauled out on the mudflats, egrets and herons stalking the shallows. Kayak Connection and Blue Water Ventures both offer rentals and guided naturalist tours. Calm, protected waters that are ideal for beginners. Bring a camera and sunscreen.

Surfing at Cowell's Beach

Daily | Cowell's Beach, Santa Cruz
Gentle waves, a sandy bottom, and a dozen surf schools ready to help you catch your first wave. Club Ed and Adventure Out both offer lessons with gear included. August has the warmest water of the year and the gentlest summer swells.

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 trees that have stood for centuries. Shaded and cool even on the warmest August day. Pair it with a stop at the Felton Farmers Market (Tuesdays) or lunch at one of the Felton cafes.

Monterey Bay Coastal Recreation Trail

18 miles from Castroville to Pacific Grove
One of the most scenic paved trails on the California coast. Walk, run, or bike along the bay with views of Cannery Row, the Monterey Peninsula, and on clear days, the entire curve of the bay. Rent a bike from Bay Bikes on Alvarado Street and ride as far as you want.

Monterey Bay Aquarium

Open daily, 10:00 AM — 5:00 PM | 886 Cannery Row, Monterey
A world-class attraction in our backyard. The Kelp Forest, the Open Sea exhibit with its schools of tuna and sharks, and the jellyfish gallery. August weekends sell out, so book ahead online.

Food & Drink Highlights

Abbott Square Market — Your All-Weekend Hub

Right in the middle of all the Jug Band Festival action, Abbott Square Market (118 Cooper Street) has become Santa Cruz's premier food hall. Grab arepas, wood-fired pizza, poke bowls, Puerto Rican dishes, craft cocktails, and local wine all under one roof. The outdoor plaza is open all weekend and is the perfect spot to refuel between events.

Santa Cruz Wine Tasting on the Westside

The Westside Santa Cruz wine trail is a short drive from downtown. Birichino Winery (204 Church Street), Storrs Winery (303 Potrero Street), and MJA Vineyards (328 Ingalls Street) all have tasting rooms open Saturday. Bottle Jack Winery and Silver Mountain Vineyards are right next door. A perfect afternoon activity between the farmers market and the Cabrillo Festival concert.

Midtown Fridays Food Trucks

Every Friday through August, Midtown Square hosts rotating food trucks alongside live music. The lineup changes weekly, so there is always something new to try. Past favorites have included tacos, barbecue, wood-fired pizzas, and Hawaiian plates.

Notable Community News

Monterey Car Week is here. August 7-16 transforms the Monterey Peninsula into the world capital of automotive culture. About one-third of all events are free, including the Kickoff Cruise-In on Alvarado Street and the Prancing Ponies Women's Car Show in Carmel. Roads and hotels will be busy, so plan ahead, book early, and leave extra time to get around the Peninsula.

The Santa Cruz Jug Band Festival returns for year two. After a successful debut in 2025, the festival expanded to four days this year with free concerts across multiple downtown venues. This is grassroots Santa Cruz at its most charming — homemade instruments, sing-alongs, and music that makes you want to tap your feet.

Tri Santa Cruz is Sunday. One of the most scenic triathlons in California, with a beachfront swim at Cowell Beach and a run along West Cliff Drive. Even if you are not racing, the spectators bring an incredible energy to Depot Park and Main Beach.

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.

Four days of jug band music in downtown Santa Cruz? Yes please. The Second Annual Santa Cruz Jug Band Festival runs Thursday through Sunday at Abbott Square, the MAH, and Pono Grill. It is free, it is weird in the best way, and it is exactly the kind of community event that makes this town special. ‍\u2728; #SantaCruzEvents #JugBandFestival #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife

My Saturday plan: Start at the Aptos Farmers Market for the best produce on the Central Coast, wander over to the Jug Band Festival at Abbott Square, catch the Cabrillo Festival Youth Ensemble concert for free, then the CONTROL program at the Civic with a world premiere by Clarice Assad. End the night with a glass of local wine on the Westside wine trail. Who is coming with me? ‍\ud83c\udf3e; ‍\ud83c\udfb6; #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #CabrilloFestival #SantaCruzLife

Car Week is officially here! The free Kickoff Cruise-In on Alvarado Street Friday night has me way more excited than I expected. Over 30 historic race cars on display, drivers in person, and the whole street turns into a car museum. Saturday and Sunday: the Pre-Reunion at Laguna Seca with historic race cars climbing the Corkscrew. Even if you are not a car person, the energy on the Peninsula is something else. ‍\ud83d\ude98; #MontereyCarWeek #MontereyBay #ThingsToDoSantaCruz #WeekendInMonterey #CaliforniaWeekend

Sunday morning energy. Cheer on the athletes at Tri Santa Cruz (first wave at 8:00 AM at Cowell Beach), then walk over to the Live Oak Farmers Market for your weekly produce haul. Cap it off with the Cabrillo Festival Grand Finale at 7:00 PM. That is the kind of Sunday that makes you grateful to live here. ‍\ud83c\udfca; ‍\ud83c\udf32; #SantaCruzEvents #WeekendInSantaCruz #SantaCruzLife #ThingsToDoSantaCruz #TriSantaCruz

Two counties, one incredible weekend. Santa Cruz has the Jug Band Festival, Cabrillo Festival world premieres, and farmers markets at peak summer. Monterey has Car Week kicking off and Los Lobos at the Golden State Theatre. You really cannot go wrong no matter which direction you drive. ‍\ud83c\udf0a; #SantaCruzEvents #MontereyBay #WeekendInSantaCruz #MontereyCarWeek #ThingsToDoSantaCruz

Enjoy the weekend, everyone. Whether you are jug-banding at Abbott Square, watching race cars at Laguna Seca, or stocking up on heirloom tomatoes at the farmers market, 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® with Century 21 Masters

Weekend Guide: Things to Do in Santa Cruz & Monterey — August 7-9