Things to do Redwood City and North Silicon Valley: October

Vicki Moore
Vicki Moore
Published on October 3, 2018

October 1 through October 8  
Fleet Week, San Francisco

October 4 through October 7
The (curious case of the) Watson Intelligence
Dragon Productions Theatre Company,  Redwood City
Playwright Madeline George weaves together the tale of three historical Watsons in this time-jumping tribute to genius. There’s Watson, the trusty sidekick to Sherlock Holmes, Watson, the loyal engineer who helped Alexander Graham Bell build the telephone, and Watson, the IBM supercomputer created to beat the Jeopardy!

All-Stars in 2011. Woven into a tale with Watson, a present day geek looking for love, the result is a story that examines the technological advancements that both bring people together and tear them apart.

A 2014 finalist for the Pulitzer Prize. 

Friday, October 5  
First Friday Family Nights CuriOdyssey, San Mateo (Free)

Live music, cash bar, wildlife, science, food and fun!

Saturday, October 6
PortFest, Redwood City (Free)

On the first Friday of every month, from 5pm until 8pm, parents and kids celebrate together at CuriOdyssey.

Dance to live music and relax with a cash bar and enjoy dinner for purchase while the kids play with seriously fun science exhibits. Visit up-close with CuriOdyssey’s Animal Ambassadors.

Enter to win a door prize for an Adopt-An-Animal of your choice. Come together as a family, meet family and friends here, or visit early and stay late.

Learn about the maritime heritage of the Port, the industrial working waterfront, and enjoy recreational activities on the San Francisco Bay. The day will include live music, children’s activities, food trucks and booths, and a beer and wine garden.

This event is free and open to all!

Sunday, October 7  
Oktoberfest Pedro Point Brewery, Pacifica

Oktoberfest comes to Pacifica at Pedro Point Brewing! In celebration, they’ll be releasing their new Hefeweizen and Sunset29 BBQ grilling up meats!

Don your dirndl or lederhosen for games and contests too!
You can also check out their swag and participate in the auction.

North Ridge Trail Hike at Purisima Creek Redwoods (Free)

3:30 PM for a lovely, moderate 4.6 mile hike along the North Ridge Trail at Purisima Creek Redwoods. Hikers will enjoy great views of redwood groves, and a sweeping overlook view.

This is a great opportunity to get outdoors, learn about POST’s involvement in protecting and preserving open space, and get a great workout (some hilly incline and descents).

Please RSVP as space is limited. 

Monday, October 8  
45th Safeway World Championship Pumpkin Weigh-Off, Half Moon Bay

First place prize money will be awarded in a “pay-by-the-pound” system with the champion receiving a hefty $7 per pound.

The Safeway World Championship Pumpkin Weigh-Off is offering a special $30,000 mega-prize for the world record breaking pumpkin at the prestigious Half Moon Bay event.

Thursday, October 11  
Murder Mystery Dinner, Redwood City
The Old Spaghetti Factory 
2107 Broadway

Midnight at the Masquerade

The rustle of silks and feathers under muted conversation was probably the last thing heard by the tragically and unexpectedly deceased at the Billionaires’ Club Annual Masquerade Ball. With a mystery under each feathery façade, unmasking the killer may be quite a challenge. It’s up to you to determine which partygoer is guilty, bring this crime to justice, and save the party!

Attend the Billionaires’ Club Annual Masquerade Ball and help get this soiree back on track by trading clues with your guests, gathering information, and solving the crime before the masked menace gets away! Evening wear, ball gowns, Venetian masks, suits, and tuxes are what to wear to this high class night of masks and murder. Get ready for a glamorous evening of mystery, intrigue, and murder.

October 12 through November 3  
Zoppé Italian Family Circus, Redwood City

Founded in Venice, Italy in 1842, the Zoppé an Italian Family Circus has been entertaining audiences for seven generations with its enchanting exhibition of European circus. For its 11th year in Redwood City, the circus brings live performances from October 12th through November 4th for spectacular shows that will enthrall the entire family!

The Zoppé Family Circus welcomes guests into an authentic one-ring circus tent, which honors the best history of the Old-World Italian tradition. Starring Nino the clown, and featuring his son Julien, the circus is propelled by a central story (as opposed to individual acts) that showcases acrobatic feats, equestrian showmanship, canine capers, clowning and plenty of audience participation. The Circus evokes something from a picture book: the clown, the trapeze, the dancing dogs, the ring and the tent, created to be reminiscent of the one-ring European family circuses of the last century and will thrill and amaze children and adults alike with its breathtaking stunts and astonishing acrobatics.

*End times on event listing are approximate.

For more information and tickets, visit:

Peninsula Farmers Markets

Saturday, October 13 & Sunday, October 14  
Silicon Valley Jazz Fest, San Carlos
Burton Park

The Silicon Valley Jazz Festival (SVJF) is a broad effort to educate the public, and especially young people, about jazz – America’s art form – and its far-reaching influence on world culture. 

Sponsored by the Kiwanis Club of San Carlos

  • A two-day jazz event featuring local school groups, Bay Area-based professional musicians and national headliners. 
  • A variety of educational activities for Peninsula school children to help them learn about the importance of jazz and the ways in which it has shaped the culture of the United States and the world. 
  • A four-week workshop to teach the rich history of jazz and the intricate techniques of jazz improvisation to local students, especially those in underserved communities.
  • A year-round series of public presentations to build the public’s awareness and appreciation of jazz. 
  • Funds for the philanthropic and volunteer activities of the Kiwanis Club of San Carlos. The festival also benefits one of the premier organizations supporting youth, families and senior citizens throughout Silicon Valley.

Saturday, Oct 13  
Facebook Festivals: Truck Yeah!  (Free), Menlo Park

Country Fest featuring a FREE Kids’ Zone, Touch-a-Truck (Emergency, Service & Military Vehicles Expo), Live Americana, Country & Bluegrass Bands, Art & Artisan Vendor Showcase, Ferris Wheel, Cooking for a Cause – Chili & BBQ Competition (100% of sales to local nonprofits, while supplies last), Farmers’ Market, and Live Music. Proceeds benefit local health services and veteran organizations.

Peninsula Oktoberfest, San Carlos
Hiller Aviation Museum
601 Skyway Road

Over two hundred years after Crown Prince Ludwig and Princess Therese of Saxony-Hildburghausen wed, the Hiller Aviation Museum joins the celebration with a special Peninsula Oktoberfest beer, bands and brats event.

Get Tickets

Sunday, October 14  
2nd Annual Bay Area Fox Trot 5K Run/Walk, San Mateo  

Coyote point park – Duck Pond
1701 Coyote point Drive
San Mateo, CA 94401

By joining us at the second annual Bay Area Fox Trot 5K Run/Walk for Parkinson’s Research,
every step you take moves us one step closer to a cure for Parkinson’s.
Runners and walkers of all experience levels, abilities and speeds are all welcome! 

Saturday, October 13 & Sunday, October 14
Half Moon Bay Pumpkin Festival

There is a ton of information about the event on their site.  The one thing it doesn’t say is that there are thousands of people who attend – and I mean thousands.  Traffic and parking are extremely difficult.  Leave early to get there and be patient.

Friday, October 19  
A Night with Janis Joplin Fox Theater Redwood City

The Tony Award-nominated Broadway musical, A Night With Janis Joplin is a musical journey celebrating Janis Joplin and the genesis of her musical genius through encounters with her seminal musical influences — Aretha Franklin, Etta James, Odetta, Nina Simone and Bessie Smith. After each encounter, we hear an explosive Joplin song incorporating those who inspired her into what became her legendary rock & roll style. 

Saturday, Oct 20  
Trio Garufa at Sam’s Castle, Pacifica  

Halloween Spooktakular, Redwood City

Kids will thrill to carnival games, proudly show off their Halloween attire in a Costume Parade at 1:30 pm, explore their way through the mysterious Monster Maze, create festive fall crafts, enjoy lots of other fun activities, and win prizes! Redwood City’s Halloween Spooktakular is suitable for kids up to age ten – admission is just $5 per child

October 24 through November 4  
Lady Washington Returns to Half Moon Bay

Lady Washington, the official tall ship of Washington State, will visit Half Moon Bay, CA on  and offer vessel tours at the dock, Evening Sails, and Adventure Sails. Vessel tours open the ships to the public for a suggested donation of $5 per person. 

Friday, October 26 
10th Annual Goblin Walk, Downtown San Carlos

San Carlos Parks & Recreation is excited for their 10th annual Goblin Walk! Children 7 years and under, accompanied by an adult, are invited to Trick-or-Treat down Laurel Street in their costume and visit the businesses displaying the Goblin Walk sign.

The first 1,000 Trick-or-Treaters can pick up a Goblin Walk Trick-or-Treat bag at Harrington Park or from any Goblin Walk volunteer.

Saturday, October 27
Kids’ Carnival and Oktoberfest, Redwood City

Kids’ Carnival and Oktoberfest is a fun-filled afternoon which features several activities planned for the young ones like a bounce house, petting zoo (sponsored by 4-H), face painting and carnival games.

Live music from our traditional “German” band, and local band “ConverGents.” The Mid Peninsula Old Time Car Club will be here with cars on display, and the Redwood City Fire and San Mateo County Sheriff Departments are also here to round out this truly community based event.

Get Tickets

Halloween Bash  The Sandwich Spot, Redwood City

Light up you lanterns, roam around to get as many candies as you want, dress up to compete for best costume and let us celebrate The Biggest Halloween Party with DJ Colin Roberts 

Dia De Los Muertos / Day of the Dead Celebration (Free), Redwood City

Celebrate this beloved Mexican holiday with art workshops, face painting, altars, traditional food and performances filled with festive dancing, colorful costumes and vibrant music. 

Wag Hotels Haunted Howloween Party, Redwood City

5th annual spooky Haunted Howl-o-ween Party at Wag Hotels to benefit California Fire Foundation. 

$10-$50 donation to help raise money for these wonderful men & women. Wag Hotels will enter you in for a chance to win a 2 night stay in a Ultra Suite if you donate at least $50 or more.

Your ticket entry to this event is a donation!

We’re turning into a haunted hotel for the day and inviting some mummies and zombies to join the pawty. Some treats will include:

Costume contest with fun prizes

Local vendors

Silent Auction

Trick-or-treat goodies

Photos with Cruella de Vil

Wag swag & prizes

And more!

Get Tickets

ObstaCourse Fitness Halloween Party!, Redwood City

DJ rockin’ the beats. Special appearances from our Zumba instructors. Costumes are encouraged. After-party to follow at a local bar for those interested.

Register online:
$10 Early Bird Special (before 10/21)
$20 Regular price (10/21-10/27)

Sunday, October 28  
OktobeRun Half Marathon, Redwood City

The 2018 RC.OktobeRun is open to runners of all levels. From competitive runners on our USA Track & Field certified half-marathon, to a 5K fun run perfect for kids and their families.

Get 10% off your registration when entering this code at checkout: CalHalf2018

Get Tickets

Wednesday, October 31
Club Fox Blues Jam presents: Halloween Blues Ball, Redwood City

Club Fox Blues Jam presents the Halloween Blues Ball with The Daniel Castro Band, Aki Goes to Bollywood & The Shari Puorto Band.

Get Tickets

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