Weekend Guide: Things to Do in Santa Cruz & Monterey, October 16-18

October's third weekend in Santa Cruz and Monterey Counties is the one I tell people to start planning early. Hundreds of local artists throw open their studio doors for the all-county Open Studios Art Tour, Wilder Ranch throws a full living-history harvest festival with heirloom apples, the city of Santa Cruz puts on its free Halloween Mask Making Festival, Thomas and Percy are at Roaring Camp in costume, and the Santa Cruz Film Festival wraps its five-day run. Farmers markets are at peak fall abundance, monarchs are drifting back into their grove, and the bay is still full of whales. Here is your share-ready guide to October 16-18, from a Santa Cruz County local of more than 50 years.

I am Kieron Bery, a REALTOR® and Pricing Strategy Advisor with Century 21 Masters, and this is the kind of weekend that reminds me why I never left. The studios, the squash, the sound of a band in a small room on a cool night, all of it is this corner of California at its best. Pick two things or pick six, just get out the door. Here is the plan.

Friday, October 16

Santa Cruz Film Festival: The Stretch Run

Wednesday through Sunday, October 14-18 | Venues across Santa Cruz County
The Santa Cruz Film Festival is in its final days, which makes this the perfect moment to catch a screening, a director Q&A, or one of the gala events before the whole thing wraps on Sunday. Independent films, documentaries, and local filmmaking show up at theaters across the county all weekend long, so grab a schedule and pick your night.

Friday Farmers Markets

Santa Cruz County Fairgrounds market, 2601 E. Lake Avenue, Watsonville: Friday, 8:00 AM to 4:00 PM
Monterey Farmers Market at Del Monte Shopping Center, 1410 Del Monte Center, Monterey: Friday, 8:00 AM to 12:00 PM
Stock the fridge before the chaos begins. Watsonville's year-round Friday market at the county fairgrounds and Monterey's Del Monte Center market are both packed with early-season apples, winter squash, greens, and the last of the warm-weather produce. Fill the cooler, then go make art and watch movies.

Saturday, October 17

Open Studios Art Tour

Saturday and Sunday, 11:00 AM to 5:00 PM | Studios across Santa Cruz County | Free
The big one. Hundreds of local artists open their studios to the public for the all-county Open Studios Art Tour this weekend, free and self-guided. Painters, ceramicists, jewelers, printmakers, and sculptors welcome you in, show their process, talk craft, and almost always have work for sale. Grab the tour guide, plot your route, and make a day of it. My advice: let the kids draw something in every studio you visit.

Wilder Ranch Heritage Harvest Festival

11:00 AM to 4:00 PM | Wilder Ranch State Park, 1401 Old Coast Road, Santa Cruz | Free admission, $10 parking
A living-history harvest party at one of the most beautiful historical ranches on the coast. Blacksmith and farm demonstrations, crafts and games, live music, food, and a heritage apple tasting hosted by the California Rare Fruit Growers. Between the pumpkins and the bluff trail ocean views, this one is pure October gold for kids and grown-ups alike.

Halloween Mask Making Festival

12:00 to 4:30 PM | London Nelson Community Center, 301 Center Street, Santa Cruz | Free
Santa Cruz's most beloved free family tradition of the fall: mask making, Halloween craft tables and carnival games, plus the legendary "Thriller" performance as the afternoon builds. Costumes welcome, supplies provided, zero pressure, one hundred percent October. This is the event I tell first-time parents to put on the calendar the moment their kid can hold a glue stick.

Festival of Monsters at the Museum of Art & History

Saturday | MAH, 705 Front Street, Santa Cruz
The MAH hosts a free, family-friendly Festival of Monsters play around Halloween season: art projects, hands-on makes, and monster-themed fun inside the downtown museum. Combine it with a walk around Abbott Square and you have a very good Saturday afternoon in downtown Santa Cruz.

Thomas & Percy's Halloween Party at Roaring Camp

Saturday and Sunday, sessions through the day | Roaring Camp Railroads, 5401 Graham Hill Road, Felton
Thomas the Tank Engine and Percy roll into the redwoods in Halloween costume for dress-up train rides, a costume contest, and a pumpkin patch. Event days run roughly 9:00 AM to 5:00 PM with set departure sessions that sell out, and the party also runs October 24-25. Plan to arrive about an hour before your departure and book at roaringcamp.com.

WOW: Women on Waves Longboard Contest (Day One)

Saturday and Sunday | Santa Cruz County surf spots
The Women on Waves Longboard Surf Contest and an open-water swim return Saturday and Sunday, an amateur longboard competition and community fundraiser that gathers the whole surf community. Spectators cheer from the sand, and if the open-water swim is your thing, entry details live at womenonwavessurfcontest.com. Local surf culture at its warmest.

Santa Cruz Band Review at the Boardwalk

Saturday | Santa Cruz Beach Boardwalk, 400 Beach Street
Marching bands from across the state take over the Boardwalk for the Santa Cruz Band Review, a beloved fall institution of music, uniforms, and adrenaline that fills the beachfront with sound. Free to wander, easy for families, and a fun way to spend a Saturday between carnival rides.

Santa Cruz Mountains Wine Passport: Celebration Day

Saturday | 35+ wineries across the Santa Cruz Mountains
The Santa Cruz Mountains Wine Passport hosts one of its 2026 celebration days on Saturday: passport holders spend the day visiting dozens of wineries for tastings, harvest pours, and food pairings across the region. Passports run about $95 for one, $160 for two, and the winery list is at winesofthesantacruzmountains.com. An all-day tasting tour of the mountains without a map of your own.

Saturday Night Live Music

The lineup to plan your night around:
The Floozies at The Catalyst, 1011 Pacific Avenue, Santa Cruz: the Colorado funk-electronic duo brings a Saturday night dance party to the big room downtown.
B-Side Players at Moe's Alley, 1535 Commercial Way, Santa Cruz: Latin-funk heavyweights in the smallest room in town; the band will fill the dance floor.
Megan Woods "The Truth Tour" at the Rio Theatre, 1205 Soquel Avenue, 7:00 PM: singer-songwriter storytelling in a beautifully intimate theater.
DNA's 13th Annual All Star Comedy Show at Kuumbwa Jazz, 320-2 Cedar Street, 7:00 to 9:00 PM: a charity comedy night in one of the warmest rooms in the county.
And if you want laughs laid on thick, the Santa Cruz Comedy Festival wraps up its week with the Grand Finale on Saturday night.

Sunday, October 18

Live Oak / Eastside Farmers Market

9:00 AM to 1:00 PM | 15th Avenue at East Cliff Drive, Santa Cruz
Sunday morning at the year-round east side market. Grab your fall haul, then walk a block to Seabright Beach for an October picnic with the waves rolling in. This is the market where you run into everyone you know, and honestly, that is my favorite part.

Marina Farmers Market

10:00 AM to 2:00 PM | 215 Reservation Road, Marina
Everyone's Harvest runs this sunny, family-friendly Sunday market in Marina, a relaxed Peninsula way to start your day before heading to the wharf or the aquarium.

Monterey Farmers Market at Del Monte Center

8:00 AM to 12:00 PM | 1410 Del Monte Center, Monterey
The Sunday session at the Del Monte Shopping Center is a late-season favorite on the Peninsula, running through the end of October, so catch it while you can. Great produce from both counties under one roof.

Open Studios Art Tour: Day Two

11:00 AM to 5:00 PM | Studios across Santa Cruz County | Free
If you ran out of time Saturday, round two of the art tour runs Sunday. Check the map, pick a neighborhood you have never really seen, and make one more handful of studio stops. I meet so many favorite neighbors for the first time at Open Studios; it never fails to make me love this community more.

Santa Cruz Film Festival: Final Day

Sunday | Venues across Santa Cruz County
The festival closes with its final screenings and a wrap celebration for the county's film community. Catch a last show Sunday evening, and save the date for next year's edition.

Thomas & Percy's Halloween Party: Day Two

Sunday sessions | Roaring Camp Railroads, 5401 Graham Hill Road, Felton
Miss Saturday's departure? Sunday sessions run the same costume train rides, costume contest, and pumpkin patch fun. Check roaringcamp.com for remaining availability before you race up the hill.

WOW Longboard Surf Contest: Day Two

Sunday | Santa Cruz County
Finals day for the longboard contest and the open-water swim. Grab coffee, hit the sand, cheer on the paddlers. It is free to watch, and the ocean decides the winner.

All Weekend: Outdoors, Family & Fall Flavors

Monarch Butterflies: Watch the Season Arrive at Natural Bridges

Monarch Grove, Natural Bridges State Park, West Cliff Drive, Santa Cruz
Mid-October is when monarchs traditionally begin arriving at the Natural Bridges grove, so this is the exact weekend to catch the first of them. Peak activity comes late November and early December, and free docent-led grove tours run weekends at 11:00 AM, with daily grove visits 11:00 AM to 4:00 PM. Walk gently, bring the kids, and start a family tradition that lasts for generations.

Whale Watching: Peak Season on the Bay

Monterey Harbor, Old Fisherman's Wharf, and watch points up the coast
October is a spectacular month for whale watching on Monterey Bay. Blue whales are still feeding into mid-October, humpbacks are migrating through, and killer whales make appearances through the fall. Tours leave from the Monterey Harbor year-round, and shore watchers can spot blows from the bluffs at Wilder Ranch and from the Point. The ocean is the biggest show in town this weekend.

Fall Beer, Wine & Cozy Pours

A few local favorites for the weekend:
Humble Sea Brewing Co., 820 Swift Street, Santa Cruz: a sunny Westside taproom with playful small-batch beers and a big patio.
Santa Cruz Mountain Brewing, 402 Ingalls Street #27, Santa Cruz: organic brews in the heart of the Westside tasting room district.
Shanty Shack Brewing, 138 Fern Street, Santa Cruz: a neighborhood taproom just off Soquel Avenue with a relaxed local crowd.
Birichino Winery, 204 Church Street, Santa Cruz: a laid-back downtown tasting room pouring Santa Cruz Mountain varietals.
MJA Vineyards, 328 Ingalls Street, and Big Basin Vineyards, 525 Pacific Avenue: two Westside tasting rooms where the grapes come from our own mountains.
Vino by the Sea, 55 Municipal Wharf, Santa Cruz: a glass of wine with an ocean view right on the wharf.
If you are on the peninsula, the Robinson Jeffers Tor House Foundation Fall Festival in Carmel runs Friday through Sunday with garden walks and poetry programs at the poet's historic stone home on beautiful Point.

Coming Up: Mark Your Calendar

Thomas & Percy's Halloween Party continues at Roaring Camp, October 24-25, if you miss this weekend. These weekends have sold out for years, so book early.

Boardwalk Fright Flicks, the free scary-movie nights on the beach, run Wednesday evenings through late October. Bring a jacket and claim a seat in the sand.

The 805 Night Market brings a street food festival to Santa Cruz, October 30 to November 1, and Halloween on the Wharf is October 31. Costume season has officially begun.

Monarch peak is on its way: late November into early December is when the grove fills with butterflies, so enjoy the early arrivals this weekend and plan a return.

Shareable Social Captions

Planning to post about the weekend? Here are some ready-to-copy captions for Instagram and Facebook, written the way I would share my own plans with friends.

Saturday is basically a festival: Open Studios throws hundreds of artist doors open across our county, Wilder Ranch is hosting a heritage harvest party with heirloom apple tasting, and the Halloween Mask Making Festival takes over the London Nelson Center. I am starting at the farm stand and ending at a studio. Who is coming with me? 🍁 🍀 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife

Parents, clear your Saturday: Thomas and Percy are rolling into Roaring Camp in Halloween costumes for dress-up train rides through the redwoods, and the free Mask Making Festival is right downtown. The kids will lose their minds, and honestly, so will I. It runs again October 24-25, so you officially have no excuse. 🚂 🎃 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife

Two counties, one golden October weekend: film festival screenings wrap Sunday, the longboard contest is on the water, the marching bands are on the beach, monarchs are drifting back to Natural Bridges, and blue whales are still feeding in the bay. October on the Central Coast is my favorite month here, and I will never stop saying it. 🌊 🦋 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay #SantaCruzLife

My full weekend script: start at the Westside market, watch a train full of costumed kids at Roaring Camp, catch the band review on the beach, a night of music downtown, and a Sunday walk for monarchs before the light goes. Send me your plans and I will meet you on the sand. 🌴 🍷 #WeekendInSantaCruz #SantaCruzEvents #SantaCruzLife #MontereyBay #ThingsToDoSantaCruz

Real talk: weeks like this are why people move here. Artists open their doors, neighbors gather in the park, and surfers share the same ocean as the whales. I could not recommend a better way to fall in love with this coast. ❤️ #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife

Enjoy the weekend, everyone. Whether you are touring studios, tasting apples at Wilder Ranch, watching your kids ride Thomas, or just wandering the wharf with a cup in the fog, I hope this October weekend gives you exactly what you need. And if you are thinking about buying or moving 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