Weekend Guide: Things to Do in Santa Cruz & Monterey, October 23-25

The weekend before Halloween in Santa Cruz and Monterey Counties is pure autumn gold: the Boardwalk fires up its famous Chili Cook-Off, Thomas and Percy roll into Roaring Camp for their final Halloween weekend, giant pumpkins come tumbling down Ocean Avenue in Carmel, Monterey throws its free California Seaweed Festival, and the Big Sur River Run sends runners into the redwoods. Monarchs are starting to gather at Natural Bridges, the pumpkin farms are in full swing, and the bay is still full of whales. Here is your share-ready guide to October 23-25, 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. Halloween here is not one night, it is a whole month of community chaos in the best way, and this is the calm-before-the-madness weekend I always look forward to. Pick your pumpkin patch, book your train tickets early, and get out the door. Here is the plan.

Friday, October 23

The 418 Project presents The Lost Boys

7:30 PM | The 418 Project, 155 South River Street, Santa Cruz
A big screen celebration of the 1986 cult classic that was filmed in Santa Cruz County, hosted by The 418 Project, the non-profit movement arts center on South River Street. Costumes welcome, the whole fun crowd, and a very October way to start the weekend. Grab tickets through Eventbrite, because this one tends to go fast.

Blippi Live! at the Golden State Theatre

6:00 PM | Golden State Theatre, 417 Alvarado Street, Monterey
If you have a toddler (or just a toddler at heart), the kid-proof live tour is the Friday night move. Bright, bouncy, built for little legs, it is a perfect first theater show for your smallest family members.

Watsonville Friday Farmers Market

8:00 AM to 4:00 PM | Santa Cruz County Fairgrounds, 2601 E. Lake Avenue, Watsonville
Stock the cooler before the weekend begins. The year-round Friday market at the fairgrounds is stacked with fall squash, apples, greens, and the last of the warm-weather produce. Fill the fridge, then go pick your pumpkin.

Saturday, October 24

Santa Cruz Beach Boardwalk Chili Cook-Off

10:00 AM to 4:00 PM | Santa Cruz Beach Boardwalk, 400 Beach Street, Santa Cruz
The Boardwalk's big smoky Saturday: pro and amateur teams cook all morning, tasting kits go on sale at 10:00 AM, the public starts tasting at 1:00 PM, and winners are announced at 4:00 PM on the Colonnade Stage. Admission is free, and a tasting kit with a bowl, spoon, and eight taste tickets is about $15. Chili in the carnival air is a fall ritual I never miss.

Thomas & Percy's Halloween Party: The Final Weekend

9:00 AM to 5:00 PM | Roaring Camp Railroads, 5401 Graham Hill Road, Felton | $25-$27 per rider, $10 parking
The last time Thomas and Percy wear their Halloween costumes this year. A roughly 25-minute train ride through the redwoods with both engines in costume, Halloween activities for the kids, and everyone out of the train car in good spirits. You should arrive about an hour before your scheduled departure, and book at roaringcamp.com because the final weekend sells out.

The Great Pumpkin Roll

11:00 AM to 1:00 PM | Ocean Avenue, Carmel-by-the-Sea | Free
The most gloriously silly thing on any calendar: Carmel closes down Ocean Avenue between Santa Rita and Junipero, lines up pumpkins, and rolls them down the hill to glorious smashes. Organizers provide the pumpkins, the sidewalk is the theater, and the sound of the crowd is half the fun. Arrive early, plant a kid with the best view, and let it happen.

California Seaweed Festival

9:00 AM to 5:00 PM | Custom House Plaza, 20 Custom House Plaza, Monterey | Free
The seventh annual edition of the largest seaweed festival in North America, right next to Fisherman's Wharf. Art, food, science, and Indigenous connections to the ocean, all of it built around the humble star of Monterey Bay. Delicious, weird, and unexpectedly wonderful, exactly the kind of Monterey thing that makes this county special.

Big Sur River Run

Race day | Pfeiffer Big Sur State Park, Big Sur
A certified, chip-timed 10K and a family-friendly 5K walk-run along the banks of the Big Sur River, with proceeds supporting local emergency services. The redwoods, the river, the fresh mountain air. One of the most beautiful race courses in California, and you get to finish it.

The Devil Makes Three at the Golden State Theatre

Saturday | Golden State Theatre, 417 Alvarado Street, Monterey
One of the great roots-country blues forces in California headlines the gorgeous Golden State on Saturday night. Expect a full, stomping, sing-along crowd in the crown jewel of Old Monterey.

Westside Santa Cruz Farmers Market

9:00 AM to 1:00 PM | Mission Street at Western Drive, Santa Cruz
The Saturday year-round market on the Westside: fall apples, squash, mushrooms, and the local growers' table. Grab your stash here, then head to the Boardwalk to watch the chili go in.

Sunday, October 25

Thomas & Percy's Halloween Party: Day Two

Sunday Sessions | Roaring Camp Railroads, 5401 Graham Hill Road, Felton
Missed Saturday? The final day of the final weekend runs the same costumed train rides through the redwoods. Check roaringcamp.com remaining availability before you race up the hill.

Easy Star All-Stars at the Golden State Theatre

Sunday | Golden State Theatre, 417 Alvarado Street, Monterey
The reggae-dub collective famous for whole-album covers like Pink Floyd's Dub Side of the Moon and Radiohead's Radiodread. A laid-back, swaying Sunday closer before the Halloween week begins.

Live Oak Sunday 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 a pumpkin-season picnic with the waves rolling in. The market where you run into everyone you know, and that is my favorite part.

Marina Sunday Farmers Market

10:00 AM to 2:00 PM | 215 Reservation Road, Marina
Everyone's Harvest runs this sunny, year-round Sunday market in Marina, rain or shine. A relaxed Peninsula way to start your day before a walk on the dunes or a visit to the aquarium.

All Weekend: Pumpkins, Monarchs & Ocean

Crystal Bay Farm Pumpkin Patch

Daily, 10:00 AM to 6:00 PM | 40 Zils Road, Watsonville | $2 entry
Opening through October 31: acres of organic pumpkins and gourds, u-pick sunflowers, weekend music, vendors, and food trucks. This is the farm-scene patch of the coastal South County, idyllic in that Watsonville way.

Borchard Farms Corn Maze

Daily, 11:00 AM to 8:00 PM through October 31 | 142 Rodgers Road, Salinas | Free
A full five-acre corn maze with a ghost town, a haunted barn, and farm animals. Free entrance, and by the end of the maze the whole family is lost together in the best way.

Everett Family Farm Stand & Earthbound Farm

2111 Old San Jose Road, Soquel, and 7250 Carmel Valley Road, Carmel Valley
Everett Family Farm has pumpkins and squash at its Soquel farm stand through late October, and Earthbound's Carmel Valley farm keeps its pumpkin patch and fall harvest events going all month. Two low-key quick stops for porch pumpkins without the crowd.

Monarch Butterflies at Natural Bridges

Monarch Grove, Natural Bridges State Beach, West Cliff Drive, Santa Cruz
Late October is prime monarch arrival season, and this is a perfect weekend to catch the first waves of butterflies settling into the eucalyptus grove. The grove is staffed daily roughly 11:00 AM to 4:00 PM, and the free weekend guided tours run at 11:00 AM and 2:00 PM. Walk gently, bring binoculars, and start a family tradition.

Whale Watching Outlook

Monterey Harbor, Fisherman's Wharf, and bluffs up the coast
Late October is still prime whale watching on Monterey Bay: humpbacks and the occasional blue whale continue to feed offshore, and the offshore day boats see action every week. Shore watchers scan the horizon from the bluffs, and the boats leave from the Monterey harbor. The ocean is the biggest show in town.

The Boardwalk All Weekend

400 Beach Street, Santa Cruz | Free admission
Rides run till late on the weekend, the arcades stay warm with the Fall Arcade Specials, and October 24-25 are bring-a-friend-free days for season pass holders. Brave the chili, brave the roller coaster, then bundle up for the spin and the ocean air.

Coming Up: Mark Your Calendar

Fright Flicks at the Boardwalk, the 21+ horror movie nights under the Grove, wraps up Wednesday, October 28 at 8:00 PM. One final screening left, tickets $15.

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

Monterey Bay Aquarium's Ocean in Motion special exhibit opens November 7, while the deep-sea wonder of Into the Deep stays through the fall, one of my favorite afternoons in Monterey.

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 with my name on it: the Boardwalk Chili Cook-Off, a whole pumpkin rolling down Ocean Avenue in Carmel, a free Seaweed Festival in Monterey, and Thomas and Percy already in costume for their very last train ride weekend. Bring a bowl, a camera, and stretchy pants. 🌶️ 🍁 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #SantaCruzLife

Parents, this is your weekend: Thomas and Percy are at Roaring Camp for their final Halloween train rides, the Great Pumpkin Roll sends pumpkins crashing down Ocean Avenue, and pumpkin patches from Watsonville to Carmel are glowing. My kids still talk about the year we watched the pumpkins smash. Make that memory. 🚂 🎃 #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife

Two counties, one big October weekend: chili at the Boardwalk, a river run into the Big Sur redwoods, reggae in Old Monterey on Sunday, and monarchs starting to fill the grove at Natural Bridges. This is the calm before Halloween week, and I plan to savor every minute. 🌊 🦋 #SantaCruzEvents #ThingsToDoSantaCruz #WeekendInSantaCruz #MontereyBay #SantaCruzLife

My full Saturday script: Westside market for groceries, chili tasting at the Boardwalk, a pumpkin roll in Carmel, and a stroll through the seaweed fest in Monterey before dinner. Send me your plans and I will see you on the sand. 🌴 🍷 #WeekendInSantaCruz #SantaCruzEvents #SantaCruzLife #MontereyBay #ThingsToDoSantaCruz

Real talk: the weekend before Halloween is when this coast is at its goofiest, warmest, most neighborly self. Chili cooks, pumpkins smash, kids ride trains in costume, and the ocean puts on a show. I could not recommend a better way to fall in love with this place. ❤️ #SantaCruzEvents #WeekendInSantaCruz #ThingsToDoSantaCruz #SantaCruzLife

Enjoy the weekend, everyone. Whether you are tasting chili on the beach, watching pumpkins fly down Ocean Avenue, riding Thomas one last time, or just wandering the monarch grove with a coffee in the fog, I hope this 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 there is nothing I love more than helping people find their home in this beautiful corner of California.

Talk soon.
Kieron Bery, REALTOR® with Century 21 Masters