Weekend Guide: Things to Do in Santa Cruz & Monterey, September 18-20, 2026

The third weekend of September is when the season shifts. The Santa Cruz County Fair rolls into Watsonville with carnival rides, a choreographed drone show, live music from a Santana lead singer, and the theme “Apple Pies and Starry Skies” that captures the feeling of early autumn in the Pajaro Valley. Down in Monterey County, GRIDLIFE Laguna Seca brings car culture and live music to WeatherTech Raceway, and the PURE Insurance Championship lets you walk the fairways of Pebble Beach alongside PGA TOUR Champions legends. Santa Cruz Shakespeare wraps its summer season under the redwoods. And the whole community turns out for Coastal Cleanup Day on Saturday morning. This is the weekend when the county fair, the racetrack, and the coastline all demand your attention at once. Here is how to do it all.

I have lived in Santa Cruz County for more than 50 years, and this particular weekend has always been one of my favorites. The county fair brings everyone together. The weather is still warm enough for beach days. The redwoods are cool and green. And there is a feeling in the air that says we are entering something special. Let me help you make the most of it.

Friday, September 18

Santa Cruz County Fair — Opening Day

Noon to 11:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Avenue, Watsonville
The 2026 Santa Cruz County Fair opens Friday with the theme “Apple Pies and Starry Skies.” Friday is the ideal day to visit — the fair is uncrowded, the exhibits are fresh, and the evening brings Andy Vargas, the lead singer of Santana, to the main stage. The fairgrounds come alive with agricultural exhibits, livestock shows, carnival rides and games, fair food classics (corn dogs, kettle corn, turkey legs, funnel cakes), and a 14-minute choreographed drone show lighting up the Pajaro Valley sky. General admission includes all exhibits, entertainment, and the drone show. Ride wristbands available separately. Children 5 and under are free every day. Friday is the perfect evening to wander the exhibits, pet the animals in the livestock barn, catch the drone show, and hear Andy Vargas channel Santana's greatest hits. I will be there.

Sandhills Sunset Yoga with Lester Estate Wines

5:30 PM to 7:00 PM | Lester Estate Wines, 2292 Alzora Road, Santa Cruz
A sunset yoga session in the Santa Cruz Mountains at Lester Estate Wines. All levels welcome. Followed by wine tasting on the terrace overlooking the vineyard. A beautiful way to ease into the weekend. Reservations required. Check lesterestatewines.com for details.

GRIDLIFE Laguna Festival — Opening Day

Gates open, check gridlife.com for schedule | WeatherTech Raceway Laguna Seca, 1021 Monterey-Salinas Highway, Salinas
GRIDLIFE Laguna Festival kicks off Friday at WeatherTech Raceway Laguna Seca. This is a major motorsports and music festival that celebrates everything about car culture: drifting, time attack racing, car shows, and live music across multiple stages. Friday is the warm-up day with practice sessions, qualifying runs, and the first car show gatherings. Weekend passes start at $35. Camping available on-site. This event draws an enthusiastic, welcoming community of car people, music fans, and anyone who appreciates the art of the internal combustion engine at speed. The legendary Corkscrew turn alone is worth the drive.

PURE Insurance Championship — Round 1

First tee time early morning | Pebble Beach Golf Links and Poppy Hills Golf Course, Pebble Beach
The PURE Insurance Championship, a PGA TOUR Champions event, tees off Friday at Pebble Beach Golf Links and Poppy Hills. This is a unique tournament: 78 legendary PGA TOUR Champions players are paired with 78 junior golfers (ages 15-18) from The First Tee program, plus 156 amateurs. Walking the fairways of Pebble Beach in September with the Monterey Bay crashing against the cliffs is one of the finest spectator experiences in golf. The junior players competing alongside the legends is what makes this event special — you might see a future major champion hit their first pro-tournament shot. Spectator passes available through pureinsureancechampionship.com.

Santa Cruz Shakespeare — Final Weekend

Evening performance, check schedule | Audrey Stanley Grove, DeLaveaga Park, Santa Cruz
Santa Cruz Shakespeare's summer season closes this weekend. Friday evening performances of Much Ado About Nothing, Macbeth, or August Wilson's Fences are the last chances to see these productions under the redwoods. After this weekend, the season shifts to fall productions of Private Lives and The Last Five Years. If you have been meaning to catch a show all summer, this is your final opportunity. Check santacruzshakespeare.org for tonight's lineup and tickets. Arrive early to walk the garden path to the grove.

Saturday, September 19

California Coastal Cleanup Day

9:00 AM to noon | Multiple locations across Santa Cruz and Monterey Counties
California's largest annual volunteer cleanup event is Saturday morning. Hundreds of sites across both counties — beaches, creeks, parks, and waterways — need volunteers to pick up trash before it reaches the ocean. In Santa Cruz County, cleanup sites include Santa Cruz Harbor, Main Beach, Seabright Beach, Capitola Beach, and the San Lorenzo River levee. In Monterey County, sites include Lovers Point, Monterey State Beach, and the Elkhorn Slough Reserve. Gloves, bags, and data cards provided. This is a wonderful family activity and a tangible way to care for the place we call home. I will be at the Santa Cruz Harbor site. Come say hello and help us clean up our coastline. Sign up at coastalcleanupday.org.

Westside Santa Cruz Farmers Market

9:00 AM to 1:00 PM | Highway 1 and Western Drive, Santa Cruz
September at the Westside market is peak harvest season. Heirloom tomatoes in every color, sweet corn, late-summer stone fruit, and the first of the fall apples and pears. Sunflowers and dahlias in buckets. Live music from local musicians weaving through the stalls. The market is fully organic-certified and has been a Santa Cruz Saturday tradition for over 15 years. Grab a coffee at the Verve stand, walk the full loop, and load up for the weekend. This is especially good timing — grab a picnic lunch here before heading to the County Fair or Coastal Cleanup Day.

Aptos Farmers Market at Cabrillo College

8:00 AM to 12:00 PM | 6500 Soquel Drive, Aptos
Voted America's Favorite Farmers Market in California three years running. Over 90 vendors with certified organic produce, artisan cheeses, pastured meats, fresh pasta, olive oils, and the Farmers Market String Band playing bluegrass. The Aptos market in September is something special — the late-summer abundance meets the first hints of autumn harvest. The apples are spectacular right now.

Scotts Valley Farmers Market

8:00 AM to 12:00 PM | 219 Mt. Hermon Road, Scotts Valley
A friendly mountain-town market with local produce and crafts. A great stop if you are starting your day in the San Lorenzo Valley area.

Santa Cruz County Fair — Day 2

10:00 AM to 11:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Avenue, Watsonville
Saturday is the biggest day of the fair. The gates open at 10:00 AM and the energy builds all day. The evening brings headliner James Durbin and The Lost Boys to the main stage for a high-energy rock show. The drone show lights up the sky after dark. All agricultural exhibits, livestock shows, and carnival rides are running at full capacity. Saturday is the day to bring the whole family, stay through the evening, and let the kids ride the Ferris wheel as the sun sets over the Pajaro Valley. Ride wristbands, fair food, and memories included.

Boardwalk PRIDE

Park opens 11:00 AM, DJ Dance Party 5:30 PM to 7:30 PM | Santa Cruz Beach Boardwalk, 400 Beach Street, Santa Cruz
The Santa Cruz Beach Boardwalk hosts Boardwalk PRIDE, an LGBTQ+ celebration that fills the park with color and community spirit. The Boardwalk opens at 11:00 AM as usual, with informational booths and giveaways from 11:00 AM to 3:00 PM. Then the DJ Dance Party takes over from 5:30 PM to 7:30 PM with music, dancing, and celebration on the midway. All rides, games, and attractions are running. The Boardwalk after Labor Day is on fall weekend hours, so this is a special event that brings the summer energy back for one more day. Free with Boardwalk admission. A wonderful way to celebrate inclusivity, community, and the last warm Saturday evenings of the season.

GRIDLIFE Laguna Festival — Day 2

Full day of racing and music | WeatherTech Raceway Laguna Seca, Salinas
Saturday is the main event at GRIDLIFE Laguna. Drifting competitions, time attack runs, car shows, and live music across multiple stages throughout the day. The Corkscrew is the most famous corner in American motorsports, and watching drivers attack it is a thrill that never gets old. The festival atmosphere includes food vendors, vendor booths, and a welcoming car-community culture. If you love cars, racing, or just want to experience the energy of Laguna Seca at full roar, this is your Saturday.

PURE Insurance Championship — Round 2

All day | Pebble Beach Golf Links and Poppy Hills Golf Course, Pebble Beach
Second round of the PGA TOUR Champions event at Pebble Beach. Saturday is traditionally the best spectator day — the cut is set, the leaders are emerging, and the pairing of legends with junior golfers creates moments you will not see at any other tournament. The ocean views from the 8th, 9th, and 18th holes are worth the ticket price alone.

Santa Cruz Shakespeare — Final Saturday

Evening performance | Audrey Stanley Grove, DeLaveaga Park, Santa Cruz
The last Saturday night of the summer season. Shakespeare under the redwoods on a September evening is as close to magic as live theater gets. Check the schedule and grab your tickets before they sell out.

Sunday, September 20

Live Oak / Eastside Farmers Market

9:00 AM to 1:00 PM | 15th Avenue and East Cliff Drive, Santa Cruz
Sunday morning market on the east side. A relaxed, neighborhood-friendly setting with local produce, artisan vendors, and the sound of waves from nearby Seabright Beach. Grab your market haul and walk a block to the sand for a September morning picnic with the ocean breeze.

Del Monte Center Farmers Market

8:00 AM to 12:00 PM | Del Monte Shopping Center, 1410 Del Monte Center, Monterey
Over 60 vendors selling local produce, artisan foods, and flowers at this lively market on the Monterey Peninsula. A perfect Sunday morning stop before exploring Cannery Row or the Coastal Recreation Trail.

Santa Cruz County Fair — Final Day

10:00 AM to 10:00 PM | Santa Cruz County Fairgrounds, 2601 East Lake Avenue, Watsonville
The final day of the 2026 Santa Cruz County Fair. Sunday is the day to bring the family one last time — the livestock auctions, the final carnival rides, the last servings of fair food, and the closing ceremonies. The fairgrounds close at 10:00 PM, earlier than Saturday, so plan accordingly. If you have not made it yet, this is your last chance. The drone show runs one final time after dark.

GRIDLIFE Laguna Festival — Final Day

Full day of racing and music | WeatherTech Raceway Laguna Seca, Salinas
Sunday at GRIDLIFE wraps up the weekend with championship races, final drifting competitions, and headliner music performances. The energy builds toward the final sessions. If you have a weekend pass, Sunday is the payoff.

PURE Insurance Championship — Final Round

All day | Pebble Beach Golf Links, Pebble Beach
The final round of the PURE Insurance Championship. The leaders tee off in the afternoon, and the championship is decided on the back nine at Pebble Beach with the Monterey Bay as a backdrop. This is the best day to walk the course and watch the drama unfold.

Santa Cruz Shakespeare — Season Finale

2:00 PM (check schedule) | Audrey Stanley Grove, DeLaveaga Park, Santa Cruz
The final performance of the summer season. Sunday matinee under the redwoods — the last chance to see this year's productions. After the final curtain, the season shifts to fall. Do not miss this.

All Weekend: Outdoor Adventures & Year-Round Favorites

Kayaking Elkhorn Slough

Daily | Moss Landing (about 20 minutes south of Santa Cruz)
September is spectacular on Elkhorn Slough. Sea otters floating among the eelgrass, harbor seals hauled out on the mudflats, and migratory shorebirds beginning their southward passage. Kayak Connection and Blue Water Ventures offer rentals and guided naturalist tours. The slough is calm and protected — ideal for beginners. Early morning is the best time to spot otters at their most active.

Hiking the Redwoods

Daily | Henry Cowell Redwoods State Park, Felton; The Forest of Nisene Marks, Aptos; Fall Creek Unit, Felton
Three world-class redwood parks within 15 minutes of each other. Henry Cowell has the easy 0.8-mile old-growth loop through trees that were already centuries old when California became a state. Nisene Marks offers 30-plus miles of trails through second-growth forest recovering into majesty. Fall Creek is quieter, following the creek through dappled September light. Mild temperatures and the first signs of autumn color in the understory make this the ideal hiking weekend.

Monterey Bay Coastal Recreation Trail

18 miles from Castroville to Pacific Grove
Walk, run, or bike along one of the most scenic paved trails on the California coast. The section between Monterey and Pacific Grove passes Cannery Row, the Monterey Bay Aquarium, and Lovers Point with panoramic views of the bay. September is the perfect month for this ride: thinner crowds and mild temperatures. Rent a bike from Bay Bikes on Alvarado Street.

Whale Watching in Monterey Bay

Daily departures | Fisherman's Wharf, Monterey, and Santa Cruz Harbor
Humpback whales are actively feeding in Monterey Bay through the fall, building their energy reserves before the long migration to Mexican waters. September offers some of the best whale watching of the year. Blue Ocean Whale Watch and Princess Monterey Whale Watching offer daily trips from both harbors. Bring a warm jacket, even on warm days — the bay breeze is cool offshore.

Monterey Bay Aquarium

Open daily, 10:00 AM to 5:00 PM | 886 Cannery Row, Monterey
The Kelp Forest, the Open Sea exhibit with schools of tuna and sea turtles, the touch pools, and the mesmerizing jellyfish gallery. September crowds are thinner than summer. Book ahead online.

Food & Drink Highlights

Santa Cruz County Fair Food

This is the fair food weekend of the year. Corn dogs, funnel cakes, turkey legs, kettle corn, cotton candy, caramel apples, and everything on a stick. The 4-H and FFA livestock barns are also worth a stop — the kids love talking about the animals they have raised. The apple pie theme is everywhere this year. Do not skip it.

GRIDLIFE Laguna Festival Food

The raceway brings in a full lineup of food vendors during the festival. From classic race-track eats to local food trucks, there is something for every appetite. The beer garden is a popular gathering spot between race sessions.

Pebble Beach Dining

If you are at the PURE Insurance Championship, the dining at Pebble Beach is an experience in itself. The Tap Room at the Lodge serves classic golf-course fare with an ocean view. The Bench is a more casual option with outdoor seating overlooking the 18th fairway. For a special evening, The Restaurant at Pebble Beach offers fine dining with windows on the ocean. Reservations required well in advance.

Abbott Square Market

118 Cooper Street, Downtown Santa Cruz
Open all weekend with a rotating lineup of food vendors. Arepas, wood-fired pizza, poke bowls, Puerto Rican dishes from Luna's Boriken Bites, and India Gourmet's beloved farmers market stand. The outdoor plaza with string lights is a perfect spot for a casual September dinner downtown.

Westside Santa Cruz Wine Tasting

The Westside wine trail is minutes from the Saturday farmers market. Birichino Winery (204 Church Street), Storrs Winery (303 Potrero Street), and MJA Vineyards (328 Ingalls Street) all have tasting rooms open on Saturday. Bottle Jack Winery and Silver Mountain Vineyards are right next door. A perfect way to spend a September afternoon between the farmers market and Boardwalk PRIDE.

Notable Community News

Santa Cruz County Fair is this weekend. The 2026 theme “Apple Pies and Starry Skies” captures exactly what makes this fair special. Andy Vargas (Santana lead singer) performs Friday. James Durbin performs Saturday. Drone show every night after dark. The fair runs Wednesday through Sunday, with full programming Friday through Sunday. General admission includes all exhibits, entertainment, and the drone show.

Boardwalk PRIDE is Saturday, September 19. The Santa Cruz Beach Boardwalk celebrates the LGBTQ+ community with informational booths, giveaways, and a DJ Dance Party from 5:30 to 7:30 PM. Free with Boardwalk admission. A beautiful celebration of community and inclusivity on the beach.

GRIDLIFE Laguna Festival at WeatherTech Raceway Laguna Seca. Three days of motorsports, car culture, and live music at one of the most iconic racetracks in the world. Drifting, time attack, car shows, and music. Weekend passes from $35.

PURE Insurance Championship at Pebble Beach. PGA TOUR Champions legends paired with junior golfers from The First Tee program. A unique tournament that combines world-class golf with an inspiring mission. Friday through Sunday at Pebble Beach Golf Links.

California Coastal Cleanup Day is Saturday, September 19. The statewide volunteer cleanup runs from 9:00 AM to noon. Sites across both counties. Gloves and bags provided. Bring the family and help keep our coastline beautiful.

Santa Cruz Shakespeare closes its summer season this weekend. Much Ado About Nothing, Macbeth, and Fences all end their runs. After this weekend, the fall productions of Private Lives and The Last Five Years begin. If you have not seen a show at the Audrey Stanley Grove this year, this is your last chance.

Capitola Beach Festival is September 26-27. The successor to the beloved Begonia Festival returns with a toy-themed celebration. Sand sculpture contest, lighted nautical parade on Soquel Creek, drone show, rowboat races, and more. Free and family-friendly. I will have full details in next week's guide.

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 plans with friends.

County fair weekend has arrived. The Santa Cruz County Fair is here with the theme “Apple Pies and Starry Skies” — carnival rides, drone shows at night, Andy Vargas from Santana on Friday, James Durbin on Saturday, and all the fair food you can handle. Then on Saturday morning I am heading to Coastal Cleanup Day at the Harbor. See you out there, friends. 🍎 ⭐ #SantaCruzEvents #SantaCruzCountyFair #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife

One weekend, three worlds. County fair in Watsonville with carnival lights and drone shows. GRIDLIFE Laguna Seca with race cars screaming through the Corkscrew. PGA legends and junior golfers at Pebble Beach. And Coastal Cleanup Day bringing the whole community together. This is why I love living here. There is always something happening. 🏁 🚗 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #MontereyBay #CaliforniaSummer

My perfect Saturday: Coastal Cleanup Day at the Harbor from 9 to noon (come help us pick up the beach). Westside Farmers Market for apples and flowers. Boardwalk PRIDE in the afternoon with the DJ Dance Party. The County Fair at night for the drone show and a corn dog. Who is joining me for any of it? 🌊 🎉 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #BoardwalkPRIDE #SantaCruzCountyFair

Family-friendly weekend, locked in. The County Fair has the rides, the animals, the drone show, and the best apple pie around. Coastal Cleanup Day is a great way to teach the kids about caring for our beaches. Boardwalk PRIDE on Saturday is a celebration everyone can enjoy. And Sunday matinee of Shakespeare under the redwoods is the kind of thing that becomes a core childhood memory. Pack the crew. 👨‍👩‍👧‍👦 🌈 #FamilyFunSantaCruz #SantaCruzEvents #WeekendInSantaCruz #SantaCruzCountyFair #ThingsToDoSantaCruz

This is the weekend summer hands off to fall. County fair season. Last Shakespeare under the redwoods. Coastal Cleanup Day on the beaches. GRIDLIFE at Laguna Seca. Golf at Pebble Beach. The farmers markets shifting from peaches to apples. And the first cool breezes carrying that autumn smell through the redwoods. September in Santa Cruz is a gift. Go enjoy it. 🌲 🌙 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife #CaliforniaAutumn

Enjoy the weekend, everyone. Whether you are riding the Ferris wheel at the County Fair, cleaning up the beach for Coastal Cleanup Day, watching drivers attack the Corkscrew at Laguna Seca, or catching the last Shakespeare performance under the redwoods, I hope this weekend gives you moments you will carry into the fall season. If you are thinking about buying or selling a home in Santa Cruz or Monterey County, 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