Weekend Guide: Things to Do in Santa Cruz & Monterey, September 25-27
This is the weekend Santa Cruz and Monterey Counties have been building toward all year. The 69th Monterey Jazz Festival opens at the fairgrounds in Monterey, the U.S. Air Force Thunderbirds headline the California International Airshow in Salinas, and the Santa Cruz Beach Boardwalk throws its free Fiesta en la Playa celebration right on the sand. Add the Santa Cruz Mountain Harvest Festival in Boulder Creek, the Duck Island Music Festival in San Lorenzo Park, outrigger canoe races at the Santa Cruz Wharf, and the Capitola Beach Festival, and this might be the most stacked weekend of the fall.
I have lived in Santa Cruz County for more than 50 years, and late-September weekends like this are why I tell people the fall stretch is the best-kept secret on the Central Coast. Every event in this guide I verified through local sources this week, so you can plan with confidence. Grab your people, pick your adventure, and get out there.
Friday, September 25
69th Monterey Jazz Festival: Opening Night
Evening performances | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
America's longest-running jazz festival opens its 69th edition Friday night and runs through Sunday. This year's headliners include Herbie Hancock, Wynton Marsalis, and Cécile McLorin Salvant, with world-class artists performing across the festival all three days. Three-day and single-day passes are on sale at montereyjazz.org. This is the event locals plan their whole fall around.
California International Airshow Salinas: Kickoff Party
Friday evening | Salinas Municipal Airport, Salinas
The weekend of aviation starts Friday night with a casual kickoff event previewing the two-day airshow that the U.S. Air Force Thunderbirds headline Saturday and Sunday. A fun way to ease into the weekend if you are heading south of the county line.
Sea Otter Viewing at Berwick Park
11:00 AM – 2:00 PM | Berwick Park, Pacific Grove
The Pacific Grove Museum of Natural History leads a free, museum-hosted sea otter viewing on Friday. The otters who call the kelp beds off Point Piños their home are endlessly entertaining, and the naturalists on hand know exactly where to look. Free. Bring binoculars if you have them.
Moe's Alley: Tania Cassette with HOLY WATER and DJ Archive 65
9:00 PM | Moe's Alley, 1535 Commercial Way, Santa Cruz
Indie pop, dreamy synths, and a DJ set at Santa Cruz's premier live music club. Moe's Alley is intimate, the sound is great, and the lineup this weekend runs deep. Tickets at moesalley.com.
The Catalyst: Santa Cruz Recording's Battle of the Bands and Mike D 5D
6:00 PM (Atrium) and 9:00 PM (main room) | The Catalyst, 1012 Pacific Avenue, Santa Cruz
Local music takes over downtown Santa Cruz on Friday. Santa Cruz Recording's Battle of the Bands 2026 fills the Atrium at 6:00 PM, and Mike D 5D follows in the main room at 9:00 PM. Two shows, one historic venue.
Felton Music Hall: Colby Acuff
Doors 7:00 PM, show 8:00 PM | Felton Music Hall, 6275 Highway 9, Felton
Honest, story-driven country from Idaho-born songwriter Colby Acuff in the cozy redwood-town music hall. 21-and-over show. The Felton Music Hall is one of the friendliest venues in the mountains, and the room is small enough that every seat is a good one.
Watsonville Farmers Market
2:00 PM – 7:00 PM | Downtown Watsonville Plaza, Peck and Union Streets, Watsonville
The Pajaro Valley's Friday tradition. Late September brings the first apples and winter squash, late-season berries, flowers, prepared foods, and a lively downtown crowd. The perfect warm-up stop before a festival weekend.
Saturday, September 26
69th Monterey Jazz Festival: Day Two
Morning through evening | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
Saturday is the festival's biggest day, with performances running from morning into the night across the grounds. Jazz clinics, seminars, art exhibits, and food from Monterey County vendors fill the time between sets. Camp at one stage and discover a new favorite, or wander and let the music pull you along. Headliners Herbie Hancock, Wynton Marsalis, and Cécile McLorin Salvant are all on the bill this weekend.
California International Airshow Salinas: Day One
Gates open 9:00 AM | Salinas Municipal Airport, Salinas
The U.S. Air Force Thunderbirds headline two days of aerobatics over the Salinas Valley. The lineup also includes Goulian Aerosports, Jason Somes and his MiG-17, Greg Colyer in a T-33, Mark Peterson in an A-37 Dragonfly, and the Bob Hoover Academy, plus static aircraft you can walk right up to and family exhibits across the ramp. Bring sunscreen, ear protection, and plenty of curiosity. The sound of afterburners sticks with you.
Fiesta en la Playa at the Santa Cruz Beach Boardwalk
Free event Saturday and Sunday; rides 11:00 AM – 8:00 PM Saturday | 400 Beach Street, Santa Cruz
The Boardwalk's free celebration of Latino heritage returns, and it is one of the friendliest weekends of the year. Expect mariachi music, folklorico dancers, and a free beach concert Saturday headlined by Banda Maguey, plus Latin-inspired food and drink specials throughout the park. Music, color, the ocean, and the old-school midway all in one place. What is not to love?
Santa Cruz Mountain Harvest Festival
1:00 PM – 6:00 PM | Junction Park, 13264 Middleton Avenue, Boulder Creek
The Santa Cruz Mountains know how to throw a harvest party. Four live bands, food and beverage booths, local artisan vendors, a petting zoo, bounce houses, arts and crafts, hay rides, kids' axe throwing, and instructed line dancing, all at Junction Park in downtown Boulder Creek. Free entry, with a small charge for the festival glass and first drink and for kids' wristbands. This year you can also walk up Middleton Avenue to the downtown Rec Center for more family activities. Organized by the Boulder Creek Recreation and Park District to benefit local nonprofits.
Duck Island Music Festival
Doors 12:00 PM, music 1:00 PM – 6:00 PM | San Lorenzo Park, 137 Dakota Avenue, Santa Cruz
A family-friendly, community-built music festival in the park, presented by Redwood Records, Moe's Alley, and The Crepe Place. The lineup spans Afrobeat, country-rock, reggae, ska, and indie rock with Mitchum Yacoub and The Brass Empire, Sonny and His Rhinestone Sunsets, Trestles, Dan P. and The Bricks, and Kaefan, plus DJ Jared between sets. Food trucks, a bar, and local vendors on the lawn. Tickets are $20 (a $15 early-bird rate was available), and kids under 12 get in free. The after-party continues at Moe's Alley that evening with Mild Universe.
34th Annual Aloha Outrigger Races and Polynesian Festival
8:00 AM – 2:00 PM, Saturday and Sunday | Santa Cruz Wharf, Santa Cruz
Free to watch and endlessly entertaining. Outrigger canoe crews race short-course sprints off the Wharf, with novice-friendly paddling for ages 12 and up, hula performances by Kūhai Hālau, and vendor booths along the pier. Grab a coffee, find a railing spot, and cheer on the paddlers. It feels like a slice of Hawaii right off our coast.
Capitola Beach Festival
Saturday and Sunday | Capitola Village and the Esplanade, Capitola
Capitola's annual beach festival brings a 3-miler fun run, a horseshoe tournament, a fishing derby, sand-sculpture activities, and a lighted nautical parade to the village by the sea. Something for every age, all in the most colorful little town on the bay. Check the Capitola calendar for exact start times and registration details.
Saturday Farmers Markets: Westside, Aptos and Scotts Valley
Westside: 9:00 AM – 1:00 PM | Highway 1 / Mission Street Extension and Western Drive, Santa Cruz
Aptos: 8:00 AM – 12:00 PM | Cabrillo College, 6500 Soquel Drive, Aptos
Scotts Valley: 8:00 AM – 12:00 PM | Graham Plaza, 219 Mt. Hermon Road, Scotts Valley
Three markets, three moods, one morning. The Westside market runs year-round rain or shine with certified organic produce and live music. Aptos brings certified organic farmers and artisan food vendors to Cabrillo College. Scotts Valley is the friendly mountain-town loop, running through November. Late September is peak apple and pear season across all three. Fill the cooler first, then head to a festival.
Kuumbwa Jazz: Martha High's Funky Divas with Fred Wesley and The New JBs
7:30 PM | Kuumbwa Jazz Center, 320 Cedar Street, Santa Cruz
Legendary soul singer Martha High, backed by a funk supergroup that includes trombonist Fred Wesley of James Brown fame, lights up one of the best jazz rooms in the country. Two of the tightest groove outfits anywhere, in an intimate downtown space. Tickets in the $48-$63 range at kuumbwajazz.org. This one will move.
Golden State Theatre: Linea Personal
8:00 PM | Golden State Theatre, 417 Alvarado Street, Monterey
Cumbia and vallenato from Stockton's Linea Personal on the "TODO O NADA" tour, in the beautifully restored Golden State Theatre downtown. Tickets $36-$112 at goldenstatetheatre.com. A fantastic counterpoint to a jazz-heavy weekend on the Peninsula.
Duck Island After Party at Moe's Alley
Evening | Moe's Alley, 1535 Commercial Way, Santa Cruz
The festival keeps rolling after dark with folkYEAH! presenting Mild Universe and special guests at Moe's Alley. If you missed the park sets, or just are not ready for the day to end, this is your Saturday nightcap. Tickets at moesalley.com.
Albatross Ridge Winery and Kitchen: Live Music with Ryan Sesma
Evening | Albatross Ridge Winery and Kitchen, Carmel Valley
Saturday evening wine and live music in Carmel Valley. Ryan Sesma plays the vineyard setting while you sip estate pours and eat from the kitchen. Great views, great wine, and a relaxed way to end a festival day on the Monterey side.
Monterey Museum of Art: Two New Exhibitions
11:00 AM – 5:00 PM | 559 Pacific Street, Monterey
"Rex Ray: We Are All Made of Light" brings the late artist's bold collage and graphic work to the museum through January, and "Born of the Bear Dance" explores contemporary Indigenous art from September 10 through December 20. Weekend visitors can join sketching in the galleries and exhibition tours. A quiet, beautiful way to spend a morning before the jazz stages heat up.
Sunday, September 27
69th Monterey Jazz Festival: Finale
Morning through evening | Monterey County Fair & Event Center, 2004 Fairground Road, Monterey
Sunday closes the festival with a full day of music and big finale sets. If you missed Saturday, you still get a complete festival day, and the Sunday crowd always has that easy, connected energy. Herbie Hancock, Wynton Marsalis, and Cécile McLorin Salvant headline this year's edition. This is the granddaddy of Monterey County events, and it does not disappoint.
California International Airshow Salinas: Final Day
Gates open 9:00 AM | Salinas Municipal Airport, Salinas
Second and final day of aerobatic displays, military demos, static aircraft, and family exhibits. Sunday shows often feature a different flying lineup, so check the schedule even if you went Saturday too. A spectacular way to close the weekend south of Santa Cruz.
Fiesta en la Playa: Final Day
Free event; rides 12:00 PM – 7:00 PM | 400 Beach Street, Santa Cruz
Sunday brings more mariachi, folklorico, and Salsa by the Sea, plus all the rides and games running through the afternoon. Sundays at the Boardwalk have a lazy, golden quality in late September. Arrive early for parking, grab something from a food stand, and let the ocean breeze do the rest.
Aloha Outrigger Races and Polynesian Festival: Day Two
8:00 AM – 2:00 PM | Santa Cruz Wharf, Santa Cruz
A second morning of outrigger racing and hula at the Wharf. Sunday often brings the longest races and the biggest crowds, so come early for parking and settle in with a breakfast burrito from one of the wharf stands.
Capitola Beach Festival: Day Two
Sunday | Capitola Village and the Esplanade, Capitola
More sand sculpture, fishing derby action, and village events to round out the weekend. The lighted nautical parade is the Saturday-evening highlight, but Sunday keeps the festival energy going all day in the village.
Live Oak / Eastside Farmers Market
9:00 AM – 1:00 PM | East Cliff Drive and 14th Avenue, Santa Cruz
The Sunday market on the east side is relaxed and neighborhood-friendly, with local produce, artisan vendors, and waves audible from nearby Seabright Beach. Grab your haul and walk down to the sand.
Roaring Camp Railroads: Santa Cruz Beach Train
Departs Roaring Camp 10:00 AM and 2:00 PM; from the Boardwalk at noon and 4:00 PM | 5401 Graham Hill Road, Felton
Ride the historic train through the redwoods and down to the Santa Cruz Beach Boardwalk, or catch it back from the Boardwalk side. Kids 2-12 ride for $31.75 and under-2s are free. On Saturday night the Moonlight Evening Dinner Train offers a redwood-lit ride through the forest. The redwood steam train also runs daily.
The Catalyst: Sleep with Pink Mountaintops
7:00 PM | The Catalyst, 1012 Pacific Avenue, Santa Cruz
Heavy, hypnotic doom-metal from Sleep, with Pink Mountaintops opening, closes out the weekend at the Catalyst. A proper Sunday night show for the loud-music crowd. Tickets at catalystclub.com.
Felton Music Hall: Spafford
Doors 6:00 PM, show 7:00 PM | Felton Music Hall, 6275 Highway 9, Felton
Arizona jam quartet Spafford brings their improvisational rock to the mountains for a Sunday night that fans travel for. 21-and-over show. Expect long, exploratory sets in a warm redwood-town room.
All Weekend: Outdoor Adventures and Family Favorites
Surfing and Surf Watching
Cowell's Beach, Steamer Lane, Pleasure Point | Santa Cruz
Late September is prime surf season in Santa Cruz, when the south swells line up clean. Watch world-class lineups at Steamer Lane off West Cliff Drive, or paddle out at the more forgiving Cowell's, where surf schools like Club Ed run lessons with gear included. On the east side, Pleasure Point and The Hook deliver consistent right point breaks. Even if you never get wet, walking West Cliff and watching the waves is a show in itself.
Kayaking Elkhorn Slough
Daily | Moss Landing, about 20 minutes south of Santa Cruz
Late September on the slough means sea otters drifting through the eelgrass, harbor seals hauled out on the mudflats, and migratory shorebirds passing through. Kayak Connection and Monterey Bay Kayaks run rentals and guided naturalist tours on calm, protected water that is ideal for beginners. Morning launches have the calmest water. Book ahead.
Hiking the Redwoods
Daily | Henry Cowell Redwoods State Park, Felton; Fall Creek Unit, Felton; Forest of Nisene Marks, Aptos
Three incredible redwood parks within 15 minutes of each other. Henry Cowell has the easy 0.8-mile Redwood Grove Loop through ancient trees more than 250 feet tall. Fall Creek offers quiet, creekside trails through second-growth forest. Nisene Marks serves up 30-plus miles of trails from flat fire roads to steep climbs. In late September the light is golden and the trails are uncrowded. Bring water and layers.
Monterey Bay Coastal Recreation Trail
18 miles from Castroville to Pacific Grove
Walk, run, or bike the old rail line along the bay. The stretch between Monterey and Pacific Grove passes Cannery Row, the Monterey Bay Aquarium, and Lovers Point with constant ocean views. Flat, easy, and spectacular. One of my favorite ways to spend a late-September afternoon.
Whale Watching: Fall Season
Daily departures | Fisherman's Wharf, Monterey, and the Santa Cruz Harbor
Late September is a golden window for whale watching in Monterey Bay. Humpbacks are feeding heavily, blue whales are still showing up through October, and killer whales are most often sighted in these months. Operators like Blue Ocean Whale Watch and Monterey Bay Whale Watch sail daily from both cities. Bring a warm jacket and your camera.
Monterey Bay Aquarium
Open daily, 10:00 AM – 5:00 PM | 886 Cannery Row, Monterey
The Kelp Forest, the Open Sea exhibit, the touch pools, and the jellyfish gallery, all with thinner crowds than peak summer. Combine it with a Coastal Trail walk and lunch on Cannery Row for a perfect Peninsula day. Book ahead online to guarantee entry.
Seymour Marine Discovery Center
Saturday and Sunday, 10:00 AM – 4:00 PM | 100 McAllister Way, Santa Cruz
Hands-on ocean science at UCSC's Long Marine Lab, including tidal touch pools, aquarium exhibits, and the world's largest blue whale skeleton. A perfect family stop that doubles as a real marine research center. Kids love it, and grown-ups learn something every time.
Wilder Ranch State Park Living History
Weekends | Wilder Ranch State Park, off Highway 1 north of Santa Cruz
The historic dairy ranch comes alive on weekends with costumed docents, blacksmithing, and farm chores, set against the old Victorian ranch buildings and miles of coastal trails. Day-use parking is $10. Wander the gardens, pet the animals, and walk the bluff trails above the surf.
U-Pick Apples: Gizdich Ranch and Sweet Water Farms
Weekends through the harvest | Gizdich Ranch, Watsonville; Sweet Water Farms, Aptos
Apple season is here. Gizdich Ranch in Watsonville is a beloved family operation with u-pick apples, fresh-pressed cider, and their famous pies. Sweet Water Farms in Aptos is a smaller, family-friendly orchard stop. Check their hours online before you go, and bring a bag that can handle more apples than you planned for.
Santa Cruz Beach Boardwalk
Open daily | 400 Beach Street, Santa Cruz
The Giant Dipper, Logger's Revenge, mini golf, laser tag, and the historic 1911 Looff Carousel all run through the weekend, with fall hours slightly shorter than summer. If you only ride one thing, make it the Giant Dipper at golden hour, when the bay turns to gold behind you.
Food & Drink Highlights
Duck Island Music Festival Food Trucks
A curated lineup of local food trucks and vendors serves the San Lorenzo Park lawn all afternoon, alongside a beer and wine bar. Eat, browse the vendors, and let the music do the talking. Kid-friendly and dog-optional, the park is the place to be Saturday afternoon.
Santa Cruz Mountain Harvest Festival Food Booths
Food and beverage booths line Junction Park in Boulder Creek, and the festival glass plus first drink is the time-honored way to do it. Mountain towns know how to feed a crowd, and the proceeds support local nonprofits. Worth the drive up the hill on its own.
Fiesta en la Playa Latin Food Specials
Latin-inspired food and drink specials run throughout the Boardwalk all weekend. Pair a ceviche or a churro with mariachi on the beach and you have a Saturday that tastes as good as it sounds.
Abbott Square Market
118 Cooper Street, Downtown Santa Cruz
Our downtown food hall on the edge of Abbott Square. Arepas, wood-fired pizza, poke bowls, Puerto Rican dishes, and India Gourmet's stand under the string lights, all open through the weekend. The outdoor plaza is one of the best people-watching spots in the county.
Monterey County Wine Country
Tasting rooms along Cannery Row pour Monterey County wines with bay views, and downtown Carmel offers a cozy cluster of rooms within walking distance of each other. Albatross Ridge adds live music in Carmel Valley on Saturday. A civilized way to spend a Peninsula afternoon between jazz sets.
Local Breweries
Discretion Brewing, Soquel; Sante Adairius Rustic Ales, Capitola; Santa Cruz Mountain Brewing, Swift Street Courtyard, Santa Cruz
Discretion pours excellent craft beer on a spacious family-friendly patio in Soquel. Sante Adairius is beloved for its mixed-fermentation saisons in Capitola. Santa Cruz Mountain Brewing keeps the Westside Swift Street Courtyard lively with organic, sustainably brewed ales. Pick a patio, gather your people, and cheers to a full weekend.
Notable Community News
The 69th Monterey Jazz Festival returns September 25-27. America's longest-running jazz festival brings Herbie Hancock, Wynton Marsalis, and Cécile McLorin Salvant to the Monterey County Fair and Event Center, with artists performing across the festival grounds all three days. A cornerstone of Monterey County culture since 1958.
The 45th California International Airshow Salinas takes flight September 26-27. The U.S. Air Force Thunderbirds headline two days of aerobatics at Salinas Municipal Airport, joined by Goulian Aerosports, Jason Somes, Greg Colyer, Mark Peterson, and the Bob Hoover Academy, with static displays and family exhibits on the ramp. Gates open at 9:00 AM both days.
Banda Maguey headlines the free Fiesta en la Playa beach concert. The Boardwalk's celebration of Latino heritage returns September 26-27 with mariachi, folklorico, Salsa by the Sea on Sunday, and a free Saturday beach concert headlined by Banda Maguey. One of the most colorful weekends at the Boardwalk all year, and free to attend.
Capitola Beach Festival is back September 26-27. The village celebrates with a 3-miler fun run, horseshoe tournament, fishing derby, sand-sculpture activities, and a lighted nautical parade along the Esplanade. Small-town charm, big weekend energy.
Fall means apples and whales. U-pick season is in full swing at Gizdich Ranch and Sweet Water Farms, and late September is a prime whale-watching window in Monterey Bay with humpbacks, blue whales, and killer whales all appearing offshore. If you have visitors coming, book a boat or a fruit box this week.
Looking ahead: Open Studios Art Tour opens in October. The 41st annual Santa Cruz County Open Studios Art Tour brings 350-plus artists opening their studios free across three weekends, from Watsonville to Davenport. After a weekend like this one, it is the perfect excuse to come back in October.
Shareable Social Captions
Planning to post about your weekend? Here are some ready-to-copy captions for Instagram and Facebook, written the way I share my own weekend plans with friends.
Jazz, jets, and mariachi, oh my. The 69th Monterey Jazz Festival brings Herbie Hancock, Wynton Marsalis, and Cécile McLorin Salvant to Monterey, the Thunderbirds headline the Salinas Airshow, and Fiesta en la Playa turns the Beach Boardwalk into a free beach party. I honestly do not know where to start. What is on your list? 🎺 🚀 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay #MontereyJazzFestival
My Saturday plan: outrigger races at the Wharf in the morning, Fiesta en la Playa mariachi at the Boardwalk, then the Duck Island Music Festival in San Lorenzo Park, all before the funky nightcap at Moe's Alley. Fifty-plus years in Santa Cruz and this town still knows how to surprise me. Who is joining? 🌊 🎼 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #FiestaEnLaPlaya
Family-friendly weekend alert. Free otter viewing in Pacific Grove, outrigger races at the Wharf, a petting zoo and hayrides at the Boulder Creek Harvest Festival, kids under 12 free at Duck Island, and the redwood train running to the Boardwalk. Pack up the crew and go. 👨👩👧👦 🌳 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #FamilyFun #BoulderCreek
Free weekend plans, sorted. Fiesta en la Playa at the Boardwalk is free, the outrigger races and Polynesian Festival at the Wharf are free, the Harvest Festival in Boulder Creek has free entry, and the sea otter viewing in Pacific Grove is free. Late September really is the best-kept secret on the Central Coast. ✨ 🌊 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #MontereyBay
Monterey Jazz or the airshow? Honestly, I am doing both. Saturday jazz at the fairgrounds with Hancock and Marsalis, Sunday Thunderbirds over Salinas, with Fiesta en la Playa and the Duck Island Festival in between. Two counties of fun in one weekend, and I could not be more ready. 🎺 🔥 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #MontereyBay #SalinasAirshow
Enjoy the weekend, everyone. Whether you are catching jazz legends in Monterey, watching the Thunderbirds over Salinas, dancing to mariachi on the Boardwalk, or riding a hay wagon in Boulder Creek, I hope this weekend gives you exactly what you need. And 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
More from Kieron Bery: Neighborhood guides | Client reviews | Last week's weekend guide | August market update | Summer living in Santa Cruz County | About Kieron