Weekend Guide: Things to Do in Santa Cruz & Monterey, September 11-13, 2026

September settles in and the Central Coast delivers one of its best weekends of the year. Two major festivals anchor both counties: the 93rd Annual Festa Italia fills Custom House Plaza in Monterey with three days of Italian food, music, and Sicilian heritage celebrations. And in Capitola Village, the 43rd Annual Art & Wine Festival brings over 125 artists, Santa Cruz Mountains wines, and live music to one of the most beautiful beachfront settings on the California coast. Plus the Boardwalk hosts its unique Fall Campout (camping under the stars on the Giant Dipper midway), reggae legends Black Uhuru at Moe's Alley, farmers markets at peak late-summer abundance, and the first signs of autumn creeping into the redwoods.

I have lived in Santa Cruz County for more than 50 years, and this transition weekend between summer and fall has always been one of my favorites. The crowds thin out. The produce shifts from peaches to apples and pumpkins. The art festivals come alive. And the golden hour seems to last just a little longer. Here is your weekend guide.

Friday, September 11

93rd Annual Festa Italia -- Opening Night

3:00 PM to 9:00 PM | Custom House Plaza, Monterey State Historic Park, Monterey
The 93rd Annual Festa Italia kicks off Friday afternoon in Old Monterey. This three-day festival celebrates Monterey's Italian Sicilian heritage and honors the local fishing community whose families have worked Monterey Bay for generations. Friday features the opening ceremonies, authentic Italian cuisine from local food vendors, live music (including headliner Pasquale Esposito and his Band), and the start of the bocce tournament. Free admission. This is the kind of festival that makes you feel like you have stepped into a Sicilian street festival. The smells alone will pull you in from a block away.

Boardwalk Fall Campout

Overnight event starting Friday evening | Santa Cruz Beach Boardwalk, 400 Beach Street, Santa Cruz
Spend the night camping on the Boardwalk. Friday evening includes setting up camp under the stars on the midway, a private movie screening on the beach, exclusive rides on the historic 1911 Looff Carousel, dinner, and free play in the Casino Arcade. Saturday morning brings breakfast, a sand sculpture competition, and a ride wristband for the day. $99.95 per person includes dinner, breakfast, camping, and Saturday rides. Benefits the American Cancer Society. Registration required at beachboardwalk.com. This is a truly unique Santa Cruz experience and it sells out every year. Perfect for families with kids or anyone who wants to see the Boardwalk from a completely different angle.

Space Heater at Moe's Alley

Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Start your weekend with high-energy live music. Space Heater brings their blend of rock and funk to Moe's Alley. $20 advance, $25 at the door. 21+. A great Friday night show to kick off a busy festival weekend.

The Growlers at Sunset Center

7:00 PM | Sunset Center, San Carlos Street between 9th and 10th, Carmel-by-the-Sea
California psych-rock band The Growlers bring their signature sound to Sunset Center in Carmel. A perfect Friday evening show on the beautiful Monterey Peninsula. Check sunsetcenter.org for tickets.

Watsonville Wednesday Market

2:00 PM to 7:00 PM | Watsonville Plaza, 358 Main Street, Watsonville
Mid-September in the Pajaro Valley means the last of the summer berries, early apples, and the first fall squash. The Watsonville market is an essential Pajaro Valley tradition with local produce, prepared foods, and a lively downtown atmosphere. A great stop on your way south to Festa Italia.

Saturday, September 12

Capitola Art & Wine Festival

10:00 AM to 6:00 PM (Saturday), 10:00 AM to 5:00 PM (Sunday) | Capitola Village, Capitola
The 43rd Annual Capitola Art & Wine Festival is one of the most scenic art festivals on the entire California coast. Over 125 juried fine artists display and sell their work along the Esplanade with the Monterey Bay as a backdrop. Santa Cruz Mountains wineries pour tastings (wine glass $20, tokens extra, 21+ with ID). Live music fills the bandstand on the beach. Food vendors line the Esplanade. Free admission. This is the kind of event where you wander for hours, discover a piece of art you did not know you needed, sip a glass of Pinot from a vineyard you can see from the bluff, and watch the sun turn the bay gold. Saturday evening is the best time to catch the sunset light over the artists' booths.

Festa Italia -- Day 2

10:00 AM to 9:00 PM | Custom House Plaza, Monterey State Historic Park, Monterey
Saturday is the biggest day of Festa Italia. The festival runs from morning through evening with expanded food offerings, live music and dancing, the bocce tournament heats, cultural performances, and cooking demonstrations. A full day of Sicilian heritage in the heart of Old Monterey. Saturday evening brings the headline musical performance and the festival hits its peak energy. Free admission. The cannoli, arancini, and fresh pasta are not to be missed.

Westside Santa Cruz Farmers Market

9:00 AM to 1:00 PM | Corner of Highway 1 and Western Drive, Santa Cruz
Mid-September at the Westside market is a beautiful transition moment. The heirloom tomatoes and sweet corn are still hanging on. The first apples and pears are appearing. Sunflowers, dahlias, and zinnias are in peak bloom. The market is fully organic-certified with live music and that Saturday morning energy that has made it a Santa Cruz institution for 15 years. Grab a coffee and walk the full loop before heading to Capitola for the art festival.

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 offering certified organic produce, artisan cheeses, pastured meats, fresh pasta, olive oils, and the Farmers Market String Band playing bluegrass in the background. The Aptos market in September is a celebration of the harvest season. The apples, pears, and late-summer stone fruit are exceptional right now.

Scotts Valley Farmers Market

8:00 AM to 12:00 PM | 219 Mt. Hermon Road / Graham Plaza, Scotts Valley
A friendly local market with mountain-town character. Local produce, crafts, and a community gathering spot. A great stop if you are starting your weekend in the San Lorenzo Valley.

Boardwalk Fall Campout -- Day 2

Morning activities, rides continue through evening | Santa Cruz Beach Boardwalk, 400 Beach Street, Santa Cruz
Saturday morning at the Fall Campout includes breakfast for campers, a sand sculpture competition, and all-day ride wristbands. Even if you did not camp overnight, the Boardwalk is open for regular operations on Saturday. The Giant Dipper, Logger's Revenge flume ride, and all the classic midway games are running. A Boardwalk day is always a good day.

Black Uhuru at Moe's Alley

Doors 8:00 PM, Show 9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Reggae royalty. Black Uhuru, the Grammy Award-winning reggae band, brings their legendary sound to Moe's Alley with special guests Native Elements. Black Uhuru has been shaping reggae music since the 1970s and their live show is powerful, soulful, and timeless. If you love reggae, do not miss this. Tickets at moesalley.com. 21+.

Chaminade Resort Vine to View Dinner with Serial Wines

Evening | Chaminade Resort, 1 Chaminade Lane, Santa Cruz
A farm-to-table wine dinner overlooking Santa Cruz and Monterey Bay. Chaminade Resort partners with Serial Wines for a multi-course dinner featuring locally sourced ingredients paired with carefully selected wines. The view from Chaminade's dining room at sunset is one of the best in the county. Reservations required. Check chaminade.com for details and pricing.

Sunday, September 13

Live Oak / Eastside Farmers Market

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

Capitola Art & Wine Festival -- Final Day

10:00 AM to 5:00 PM | Capitola Village
Sunday at the Capitola Art & Wine Festival is a little quieter, a little more relaxed. The same 125-plus artists are there, the wine tastings are flowing, and the live music continues. Sunday is a wonderful day to browse at a leisurely pace. Arrive early to find parking in Capitola Village.

Festa Italia -- Final Day

10:00 AM to 6:00 PM | Custom House Plaza, Monterey State Historic Park, Monterey
The final day of Festa Italia wraps up Sunday evening. The bocce tournament concludes, the last servings of cannoli and arancini are ladled out, and the festival closes with final performances. If you have not made it to Monterey yet, this is your last chance. Free admission.

Del Monte Center Farmers Market

8:00 AM to 12:00 PM | Del Monte Shopping Center, 1410 Del Monte Center, Monterey
The seasonal Sunday Del Monte market continues with over 60 vendors offering local produce, artisan breads, flowers, and specialty foods. A perfect morning stop on the Monterey Peninsula before heading to Festa Italia or exploring Cannery Row.

Magic Sword with Skylimit at Moe's Alley

Doors 7:00 PM, Show 8:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
(((folkYEAH!))) presents Magic Sword with Skylimit. Magic Sword is an electronic music and visual project known for their immersive, synth-driven performances and comic-book aesthetic. A unique Sunday evening show. $20 advance, $25 at the door. 21+.

Santa Cruz Shakespeare: Matinee Performances

2:00 PM (check schedule for play) | Audrey Stanley Grove, DeLaveaga Park, Santa Cruz
Santa Cruz Shakespeare continues its season through September 19. Sunday afternoon matinees are a sublime way to experience live theater under the redwoods. Much Ado About Nothing, Macbeth, and August Wilson's Fences are all running on rotating schedules. Check santacruzshakespeare.org for this Sunday's lineup and tickets. The fall productions Private Lives and The Last Five Years open soon, so this is your last chance for the summer Shakespeare blockbusters.

All Weekend: Outdoor Adventures & Year-Round Favorites

Kayaking Elkhorn Slough

Daily | Moss Landing (about 20 minutes south of Santa Cruz)
September is one of the best months on Elkhorn Slough. Sea otters floating among the eelgrass, harbor seals hauled out on the mudflats, and migratory shorebirds beginning to pass through. Kayak Connection and Blue Water Ventures offer rentals and guided naturalist tours. Calm, protected waters that are ideal for beginners. Early morning is the best time to see the 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 spectacular redwood parks within 15 minutes of each other. Henry Cowell has the easy 0.8-mile old-growth loop through trees that have stood for centuries. Nisene Marks offers 30-plus miles of trails from flat fire roads to steep climbs through second-growth forest. Fall Creek is quieter and follows the creek through dappled sunlight. September brings mild temperatures and the first hints of autumn color in the understory. Bring water and layers.

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 views of the bay. Rent a bike from Bay Bikes on Alvarado Street. September is ideal for this ride: the summer crowds have thinned and the temperatures are perfect.

Whale Watching in Monterey Bay

Daily departures | Fisherman's Wharf, Monterey, and Santa Cruz Harbor
Humpback whales are still actively feeding in Monterey Bay through early fall. Half-day tours depart from both Monterey's Fisherman's Wharf and the Santa Cruz Harbor. Blue Ocean Whale Watch and Princess Monterey Whale Watching offer daily trips. Bring a warm jacket. September has some of the best whale watching of the year as the whales feed heavily before their migration.

Santa Cruz Beach Boardwalk

Open weekends (after Labor Day schedule) | 400 Beach Street, Santa Cruz
After Labor Day, the Boardwalk runs on weekends only. The Giant Dipper, Logger's Revenge, mini golf, laser tag, and the historic Looff Carousel are all open on Saturday and Sunday. The Boardwalk Bowl Summer Fun Pass is valid through September 7, but individual ride tickets and wristbands are available. Fall weekends at the Boardwalk have a special charm: fewer crowds, cooler ocean breezes, and the lights reflecting on the sand in the early darkness.

Monterey Bay Aquarium

Open daily, 10:00 AM to 5:00 PM | 886 Cannery Row, Monterey
A world-class attraction right in our backyard. The Kelp Forest, the Open Sea exhibit with schools of tuna and sea turtles, the touch pools, and the mesmerizing jellyfish gallery. September is an excellent time to visit with thinner crowds than peak summer. Book ahead online to guarantee entry.

Food & Drink Highlights

Festa Italia Food

This is the food event of the weekend. Three full days of authentic Italian cuisine at Custom House Plaza in Monterey. Fresh cannoli, arancini (rice balls), pasta dishes, grilled sausages, and the famous Italian tri-tip sandwiches. Plus wine and beer from Monterey County producers. The cooking demonstrations are fascinating. Come hungry and pace yourself.

Capitola Art & Wine Festival

Santa Cruz Mountains wineries pour tastings all weekend. A Festival Glass costs $20, tasting tokens are extra. Over 125 artists to browse between sips. Food vendors line the Esplanade with everything from festival fare to gourmet bites. The combination of art, wine, and beach setting is hard to beat.

Chaminade Vine to View Dinner

Saturday evening's farm-to-table wine dinner at Chaminade Resort. Multi-course dinner with Serial Wines pairings, overlooking the entire Monterey Bay at sunset. An elevated dining experience for a special weekend date night.

Abbott Square Market

118 Cooper Street, Downtown Santa Cruz
Open all weekend. Arepas, wood-fired pizza, poke bowls, Puerto Rican dishes from Luna's Boriken Bites, and India Gourmet's famous farmers market stand-by-night offerings. The outdoor plaza is a perfect spot for a casual dinner on a warm September evening. Grab a table under the string lights and watch downtown Santa Cruz do its thing.

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 Saturday. Bottle Jack Winery and Silver Mountain Vineyards are right next door. A perfect afternoon pairing with your market haul before heading to Capitola.

Notable Community News

93rd Annual Festa Italia returns to Custom House Plaza September 11-13. Three days of Italian Sicilian heritage, authentic cuisine, live music, bocce, and cultural performances in Old Monterey. The festival honors Monterey's fishing community and their generations of tradition. Free admission. This is one of Monterey's most cherished annual events.

43rd Annual Capitola Art & Wine Festival is this weekend. Over 125 juried fine artists, Santa Cruz Mountains wine tastings, live music, and food vendors along the Esplanade in Capitola Village. Free admission. Wine tastings require a Festival Glass ($20) and tokens. One of the most scenic art festivals on the Central Coast.

Boardwalk Fall Campout returns. Camp under the stars on the Santa Cruz Beach Boardwalk, Friday night through Saturday. Includes dinner, breakfast, ride wristbands, a private movie on the beach, and a sand sculpture competition. $99.95 per person. Benefits the American Cancer Society. A unique Santa Cruz experience that sells out every year.

Santa Cruz Shakespeare season finale approaching. The summer season runs through September 19 at Audrey Stanley Grove in DeLaveaga Park. Much Ado About Nothing, Macbeth, and Fences are still on the rotating schedule. After that, the fall productions Private Lives and The Last Five Years begin. Summer Shakespeare under the redwoods is not something to miss.

Santa Cruz County Fair coming September 16-20. The theme for 2026 is "Apple Pies and Starry Skies." Agricultural exhibits, livestock shows, carnival rides, live entertainment, and family activities at the Santa Cruz County Fairgrounds in Watsonville. I will have a full guide in next week's post.

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.

Two festivals, one unforgettable weekend. The 43rd Annual Capitola Art & Wine Festival along the beach with 125 artists and local wines. Plus the 93rd Annual Festa Italia in Monterey with cannoli, arancini, live music, and Sicilian heritage celebrations. Between the two, there is art, wine, food, and ocean views all weekend. Who is joining me? 🎨 🍷 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay #CapitolaArtAndWine

Weekend game plan: Saturday morning at the Westside Farmers Market for late-summer peaches and the first of the apples. Then the Capitola Art & Wine Festival along the Esplanade. Sunday: Festa Italia in Monterey for the best Italian food on the Central Coast. Ending the weekend with Black Uhuru at Moe's Alley. See you out there. 🍋 🎼 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #MontereyBay

Family-friendly weekend alert. Camp overnight on the Santa Cruz Beach Boardwalk with the Fall Campout (dinner, breakfast, rides, movie on the beach included). The Capitola Art & Wine Festival has art activities and a beautiful beachfront setting kids will love. Festa Italia in Monterey has cooking demos, bocce, and cultural performances for all ages. Pack the crew and go. 👨‍👩‍👧‍👦 🎪 #FamilyFunSantaCruz #SantaCruzEvents #WeekendInSantaCruz #Capitola #MontereyBay

Mid-September energy is different. The summer crowds are gone. The farmers markets are shifting from peaches to apples. The art festivals fill the beachfront. And the golden hour seems to stretch a little longer. This weekend has festivals, wine, live music, redwood hikes, and the best cannoli on the Central Coast. This is my favorite season in Santa Cruz. Come see why. 🌊 🌲 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife #CaliforniaAutumn

Mark your calendar already. This weekend: Capitola Art & Wine Festival and Festa Italia. Next week: Santa Cruz County Fair (September 16-20, theme "Apple Pies and Starry Skies"). Fall season is packed with community events. I will have a full County Fair guide coming soon. Stay tuned. 🍎 ⭐ #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzCountyFair #MontereyBay

Enjoy the weekend, everyone. Whether you are sipping wine at the Capitola Art Festival, eating cannoli at Festa Italia in Monterey, or camping under the stars on the Boardwalk, 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