Weekend Guide: Things to Do in Santa Cruz & Monterey, September 25-27, 2026

Late September is the sweet spot on the Central Coast, and this year it lands on a truly stacked weekend. The 69th Annual Monterey Jazz Festival fills the fairgrounds in Monterey with 500-plus artists across eight stages, while the 45th Annual California International Airshow Salinas brings the U.S. Air Force Thunderbirds over the Salinas Valley. Closer to home, the Santa Cruz Beach Boardwalk throws Fiesta en la Playa, a free two-day celebration of Latino heritage with mariachi, folklorico, and a concert on the beach. And up in Boulder Creek, the Santa Cruz Mountain Harvest Festival turns Junction Park into a mountain-town block party.

I have lived in Santa Cruz County for more than 50 years, and late September has always been my favorite kind of weekend: the summer crowds thin out, the fog takes more days off, and the community events come in waves. Whether you are chasing world-class jazz, watching fighter jets, dancing to mariachi on the sand, or riding a hay wagon at a mountain harvest festival, there is something here for you. Grab your people and go. Here is your guide.

Friday, September 25

69th Annual Monterey Jazz Festival -- Opening Night

Evening performances into the night | Monterey County Fairgrounds, 2004 Fairground Road, Monterey
America's longest-running jazz festival kicks off Friday evening. With 500-plus artists across eight stages, plus jazz clinics, seminars, and art exhibits, this is as much about discovering your next favorite musician as it is about the legends. Three-day and single-day passes are available at montereyjazz.org. This is the event locals plan their whole fall around.

California International Airshow Salinas -- "Maverick's Lounge" Kickoff Party

Friday evening | Salinas Municipal Airport, Salinas
The weekend's aviation celebration starts Friday night with its kickoff party, a casual evening to preview the two-day airshow that the U.S. Air Force Thunderbirds headline Saturday and Sunday. A great way to start the weekend if you are heading south of the county line.

Watsonville Farmers Market

2:00 PM to 7:00 PM | Watsonville Plaza, 358 Main Street, Watsonville
The Friday market in the Pajaro Valley is an essential weekly ritual. Late September brings the first apples and squash, late-season berries, flowers, prepared foods, and a lively downtown crowd. A perfect warm-up stop before a festival weekend, or a quiet Friday errand if festivals are not your thing.

Saturday, September 26

Fiesta en la Playa at the Boardwalk

Daytime into evening, Saturday and Sunday | Santa Cruz Beach Boardwalk, 400 Beach Street, Santa Cruz
The Boardwalk's free celebration of Latino heritage is one of the friendliest weekends of the year. Expect mariachi music, folklorico dancers, a free beach concert, and Latino food and drink specials throughout the park, plus all the rides and games that make the Boardwalk the Boardwalk. Free admission. 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 to 6:00 PM | Junction Park, Boulder Creek
The Santa Cruz Mountains know how to throw a harvest party. Four live bands, food and drink booths, local artisans, a bounce house, petting zoo, axe throwing, instructed line dancing, and hay rides all set in Junction Park up in Boulder Creek. Free admission, though there is typically a parking or event fee. The mountain air alone is worth the drive, and this is the kind of event where you run into everyone you know and leave with new friends.

Monterey Jazz Festival -- Day Two

Morning through evening | Monterey County Fairgrounds, 2004 Fairground Road, Monterey
Saturday is the biggest day of the festival, with performances running across eight stages from morning into the night. Jazz clinics, seminars, art exhibits, and food from Monterey County vendors fill the grounds between sets. Camp out at one stage and discover a new favorite, or wander and let the music pull you along.

California International Airshow Salinas -- Day One

Gates open in the morning | Salinas Municipal Airport, Salinas
The U.S. Air Force Thunderbirds headline the two-day show, with military and civilian aerobatic teams, static aircraft you can walk right up to, interactive exhibits, and family activities across the ramp. Bring sunscreen, ear protection, and plenty of curiosity for the kids. The sound of afterburners over the Salinas Valley sticks with you.

Saturday Farmers Markets: Westside, Aptos & Scotts Valley

Westside: 9:00 AM to 1:00 PM | corner of Highway 1 and Western Drive, Santa Cruz
Aptos: 8:00 AM to 12:00 PM | Cabrillo College, 6500 Soquel Drive, Aptos
Scotts Valley: 8:00 AM to 12:00 PM | 219 Mt. Hermon Road, Graham Plaza
Three markets, three moods, one morning. The Westside is organic-certified with live music and that famous Saturday energy. The Aptos market brings 70-plus vendors and bluegrass to Cabrillo College. Scotts Valley is the friendly mountain-town loop. Late September is peak apple and pear season across all three. Fill the cooler first, then head to a festival.

Abbott Square Market -- Live Music

Saturday evening | 118 Cooper Street, Downtown Santa Cruz
Abbott Square keeps its fall rhythm with live music from Ryan Price & Friends on Saturday evening. Arepas, wood-fired pizza, poke bowls, India Gourmet, and the string-lit plaza come alive with people. A perfect casual dinner stop before or after Fiesta en la Playa.

Happy Girl Kitchen -- "We Bought the Building" Celebration

Saturday | Pacific Grove
A true community milestone: Happy Girl Kitchen celebrates buying its own building in Pacific Grove with music and food. The kind of small-town gathering that makes the Monterey Peninsula special. Stop by, congratulate the owners, and grab something delicious while you are there.

Sunday, September 27

Fiesta en la Playa -- Final Day

Daytime into evening | Santa Cruz Beach Boardwalk, 400 Beach Street, Santa Cruz
Sunday brings another full day of mariachi, folklorico, and the free beach concert, with all rides and games running. 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.

Monterey Jazz Festival -- Finale

Morning through the evening finale | Monterey County Fairgrounds, 2004 Fairground Road, Monterey
Sunday is the festival's closing day, with lineups running through the evening and big-name finale sets. If you missed Saturday, you still have a full day of world-class jazz ahead of you. If you have never been, this is the year to go. This is the granddaddy of Monterey County events, and it does not disappoint.

California International Airshow Salinas -- Final Day

Gates open in the morning | 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.

Live Oak / Eastside Farmers Market

9:00 AM to 1:00 PM | 15th Avenue and East Cliff Drive, 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.

El Mercado Popular at the Santa Cruz County Fairgrounds

8:00 AM to 4:00 PM | 2601 East Lake Avenue, Watsonville
A lively Sunday institution in Watsonville: the certified farmers market alongside a bustling flea market, with produce, food stalls, and a true community gathering on the fairgrounds. Well worth the drive south.

Abbott Square Market -- Salsa by the Sea Afterparty

Sunday evening | 118 Cooper Street, Downtown Santa Cruz
End the weekend the way downtown Santa Cruz likes to: with a salsa, bachata, and merengue DJ dance party at Abbott Square. Free outdoor dancing under the lights. Even if you have two left feet, the people-watching is top tier.

All Weekend: Outdoor Adventures & Year-Round Favorites

Surfing the Late-September Swells

Steamer Lane, Cowell's, Pleasure Point | Santa Cruz
Late September is prime surf season on the south swells, when waves line up best. Watch the world-class breaks at Steamer Lane off West Cliff Drive, or paddle out at the more forgiving Cowell's for beginners. On the east side, Pleasure Point and The Hook deliver consistent right point breaks. Even if you are not surfing, walking West Cliff and watching the lineups 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 floating among the eelgrass, harbor seals hauled out, and migratory shorebirds passing through. Monterey Bay Kayaks runs guided naturalist tours, and Kayak Connection offers rentals and lessons. Calm, protected water that is ideal for beginners. Book ahead, morning launches have the calmest water.

Hiking the Redwoods

Daily | Henry Cowell Redwoods State Park, Felton; Forest of Nisene Marks, Aptos
Mild temperatures, dappled light, and the first hints of autumn color in the understory. Henry Cowell has the easy 0.8-mile Redwood Grove Loop through ancient trees over 250 feet tall. Nisene Marks offers 30-plus miles of trails from fire roads to steep climbs. Both are within 15 minutes of each other. Bring 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 -- Peak Fall Season

Daily departures | Fisherman's Wharf, Monterey, and the Santa Cruz Harbor
Right now is one of the best whale-watching windows of the entire year in Monterey Bay. Blue whale season runs through October, humpbacks are feeding heavily, and killer whales are most often sighted from late August through October. Operators like Blue Ocean Whale Watch and Monterey Bay Whale Watch sail daily. Bring a warm jacket and your camera.

Monterey Bay Aquarium

Open daily, 10:00 AM to 5:00 PM | 886 Cannery Row, Monterey
The Kelp Forest, Open Sea exhibit, 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.

Food & Drink Highlights

Santa Cruz Mountain Brewing

402 Ingalls Street, Suite 27 (Swift Street Courtyard), Santa Cruz
Organic, sustainably brewed ales with seven flagships plus seasonal taps in the breezy Swift Street Courtyard. A great post-market, pre-festival pour, especially if you are already on the Westside.

Sante Adairius Rustic Ales

103 Kennedy Drive, Capitola (and The Portal, 1315 Water Street, Santa Cruz)
Beloved for their mixed-fermentation saisons, Sante Adairius pours in Capitola, with the Santa Cruz outpost The Portal keeping the Water Street crowd happy. One of the most celebrated breweries on the Central Coast.

Alvarado Street Brewery & Peter B's Brewpub

426 Alvarado Street, Monterey; Peter B's at the Portola Hotel & Spa, Monterey
In Monterey, refuel between jazz sets with hazy IPAs and wood-fired pies at Alvarado Street, or head to Peter B's, the area's classic family-friendly brewpub. Beer, local bites, and post-festival energy.

Wine Tasting on Cannery Row & Beyond

Cannery Row, Monterey; downtown Carmel-by-the-Sea
Tasting rooms along Cannery Row pour Monterey County wines with bay views, and downtown Carmel offers a cozy cluster of rooms walking distance from each other. A mellow wine-tasting lap is a civilized way to spend a Peninsula afternoon.

Abbott Square Market Food Stalls

118 Cooper Street, Downtown Santa Cruz
Arepas, wood-fired pizza, poke bowls, Puerto Rican dishes, and India Gourmet's stand under the string lights. Open all weekend, and the perfect stopping point between the Boardwalk and a show. Come hungry.

Notable Community News

The 69th Annual Monterey Jazz Festival returns September 25-27. America's longest-running jazz festival brings 500-plus artists to eight stages at the Monterey County Fairgrounds, with clinics, seminars, art exhibits, and a festival village. A cornerstone of Monterey County culture since 1958.

The 45th Annual California International Airshow Salinas takes flight September 26-27. The U.S. Air Force Thunderbirds headline two days of aerobatic demos, static displays, and family activities at Salinas Municipal Airport, with a Friday-evening kickoff party to start the weekend.

Fiesta en la Playa returns to the Santa Cruz Beach Boardwalk September 26-27. A free two-day celebration of Latino heritage with mariachi, folklorico, a beach concert, and food and drink specials throughout the park. One of the most colorful weekends at the Boardwalk all year.

Santa Cruz Mountain Harvest Festival fills Boulder Creek on Saturday, September 26. Four bands, food and drink booths, artisans, a petting zoo, axe throwing, line dancing, and hay rides at Junction Park. A free-admission mountain-town celebration.

Late September is peak whale-watching season in Monterey Bay. Blue whales, humpbacks, and killer whales are all showing up right now, and trips depart daily from Monterey and Santa Cruz. If you have visitors coming, this is the weekend to book a boat.

Looking ahead: First Friday Santa Cruz returns October 2. Downtown galleries, pop-ups, and the art walk that makes the first Friday of each month feel like a block party. A perfect excuse to come back to Santa Cruz the following weekend.

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.

Jazz, jets, and mariachi, oh my. The 69th Monterey Jazz Festival fills eight stages in Monterey, the Thunderbirds headline the airshow in Salinas, and Fiesta en la Playa brings free mariachi concerts to the Beach Boardwalk. There is so much happening this weekend I do not know where to start. What is on your list? 🎺 🚀 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay #MontereyJazzFestival

My Saturday: farmers market haul in the morning, Fiesta en la Playa at the Boardwalk in the afternoon, and live music at Abbott Square at night. Between the ocean, the mariachi, and the string lights, it is going to be a good one. Who is joining me? 🌊 🎼 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife #FiestaEnLaPlaya

Family-friendly weekend alert. El Mercado Popular farmers market in Watsonville, Fiesta en la Playa with rides and games at the Boardwalk, and a petting zoo and hayrides up in Boulder Creek at the Mountain Harvest Festival. The airshow has static aircraft the kids can walk right up to. Pack the crew and go. 👨‍👩‍👧‍👦 🌊 #FamilyFunSantaCruz #SantaCruzEvents #WeekendInSantaCruz #Watsonville #BoulderCreek

Late September energy is different. The summer crowds are gone, the fog takes more days off, and the Monterey Bay is full of whales. Jazz on eight stages, planes over the valley, and hayrides in the mountains. If you have been looking for the perfect weekend to fall in love with the Central Coast, this is it. 🐋 🌲 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay #CaliforniaAutumn

Monterey Jazz or the airshow? Honestly, I am doing both. Saturday jazz at the fairgrounds, Sunday Thunderbirds over Salinas, with stops at the Boardwalk and Abbott Square in between. Two counties of fun in one weekend and I could not be more excited. Send me your favorites. 🎺 🔥 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #MontereyBay #SalinasAirshow

Enjoy the weekend, everyone. Whether you are catching a jazz legend 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