Please note: This is an older article that was published over 3 years ago. It may contain outdated information, so please double-check any dates, hours, or other information before confirming your plans. Thank you!

The Half Moon Bay Coastside truly comes to life during the fall and early winter season. Pumpkins abound, of course (they don't call us the Pumpkin Capital of the World for nothing), but there's so much more to see and do. Here are just some of the highlights of the coming months.

Cool Harbor Nights Car Show 

The First Thursday of Every Month - 3 p.m. to Sunset (free!)
Car aficionados far and wide descend upon Pillar Point Harbor for Cool Harbor Nights, a coastal car and motorcycle show. Owners of classic cars, trucks, fancy motorcycles and hot rods have the opportunity to show off their pride and joy while providing a glimpse of early automotive and motorcycle technology. Many of the machines have taken years to create or restore. Families will enjoy the cruise down memory lane as they show their kids the vintage Mustang or hot muscle car just like they drove. Registered machines will be entered into a drawing for some fantastic prizes. The event is free and open to both exhibitors and spectators. Pillar Point Harbor on Johnson Pier, Princeton-By-The-Sea. For more information and/or to register as a participant, contact Mary Botham, (650) 726-2722, [email protected].

The Mavericks Experience Tour

Sept. 9, 1 p.m. - 3 p.m. (free!)
As September officially kicks off the big wave winter season, The Mavericks Experience will host a free guided tour hosted by Tim West, who has been surfing Mavericks and the surrounding coast for nearly 20 years. Stroll along the harbor trail from the Mavericks parking lot all the way out to the beach overlooking Mavericks as West explains the historical details about the harbor, community, and Mavericks. In addition, there will be a Q & A with Mavericks surfers of past and present who have either surfed in the Mavericks contest or are a major influence on Mavericks. Donations are recommended for the tour; proceeds go to the Half Moon Bay Surf Club. Mavericks Parking Lot (also known as Tide Pool's Parking Lot on Google maps). For reservations, contact Tim West, [email protected], (650) 727-4455.

Barrel to Bottle Days

Sept. 22, Nov. 3, Nov. 10, & Dec. 8
Wine lovers can take part in a tradition known as “Barrel to Bottle” at La Nebbia Winery by bringing in their empty wine bottles and getting them filled with La Nebbia’s own wine. Guests can even bring in their own custom labels and La Nebbia will apply them to the bottle during the event, making for a fun conversation starter or a great gift. On September 22, refill bottles with a delicious red wine. On November 3, customers can indulge in a white wine, and November 10 and December 8 are once again perfect for red wine lovers. Barrel to Bottle pricing starts at $6 per 750ml bottle; 12341 San Mateo Road, (650) 726-9463,

11th Annual Hand-Blown Art Glass Pumpkin Patch

Oct. 6-7, 10 a.m. - 5 p.m.
Half Moon Bay Art Glass will transform the grounds of La Nebbia Winery into a glistening glass pumpkin patch featuring the work of glass blower Douglass C. Brown. This artistic installation will feature hundreds of one-of-a-kind glass pumpkins available for purchase, each one personally handcrafted by Brown, who works year round to create this spectacular display. La Nebbia Winery will be open for guests to partake in wine tasting and to purchase bottles of wine, while bocce ball courts will offer fun for everyone. For those who wish to create their own piece of art, HMB Art Glass is offering several classes year around. Classes start as low as $40 + tax for kids 6 years old and above. Ask for the "NewClient50" special rate for up to 50% off website pricing. La Nebbia Winery, 12341 San Mateo Road on Hwy. 92, (650) 283-5626,

16th Annual Bernese Mountain Dog Day

Oct. 7, 9 a.m. – 3 p.m. (free!)
Farmer John’s pumpkin patch is sponsoring the 16th Annual Mountain Dog Day! Last year, there were over 130 Bernese Mountain Dogs who visited Farmer John’s pumpkin patch. Berner friends will be accompanied by John’s Bernese, Miss Cora, along with her cousin Miss Chloe who will welcome their old and new pals. Farmer John will be ready to give hayrides for his furry friends. 800 North Cabrillo Highway, (650) 726-4980,

45th Annual Safeway World Championship Pumpkin Weigh-Off 

Oct. 8, 7 a.m. - 11 a.m. (free!)
Superstar Gourd Growing Greats and their hard-to-believe, titanic orange orbs gather for the Safeway World Championship Pumpkin Weigh-Off in the World Pumpkin Capital of Half Moon Bay. A special $30,000 bonus mega-prize will be awarded to any grower who breaks the world record at Half Moon Bay, considered the "Super Bowl of Weigh-Offs." A host of veteran growers contend for the coveted title, the $30,000 world record prize and thousands in additional prize money. In a pay-by-the-pound system, the winner will take home a hefty $7 per pound for the champion mega-pumpkin. Superstar grower Joel Holland’s mighty 2,363-pound weigh-off champion mega-gourd obliterated a formidable field of heavyweight contenders in winning the 2017 Safeway World Championship Pumpkin Weigh-Off. The grand champion gourd (along with the top five overall) will be on display at the Half Moon Bay Art & Pumpkin Festival on October 13-14. IDES Grounds, 735 Main Street, (650) 726-9652,

48th Annual Half Moon Bay Art & Pumpkin Festival 

Oct. 13 & 14, 9 a.m. – 5 p.m.  (free!)
Half Moon Bay celebrates its bountiful fall harvest and autumn splendor with a special weekend filled with enormous heavyweight champion pumpkins, four stages of blockbuster entertainment, the Great Pumpkin Parade, a bone-chilling Haunted House, harvest-inspired crafts, home-style foods, expert pumpkin carver Peter Hazel sculpting a monster 10,000+ pound pumpkin, photos with the grand champion mega-gourd, pie-eating and costume contests, pumpkin carving for fun, and so much more! With so much to see and do, visitors can use iPumpkin, the official mobile application of the Half Moon Bay Art & Pumpkin Festival, to navigate their way through the festival. Main Street, (650) 726-9652,

Fifth Annual Coastside Brewfest 

Oct. 20, 1 p.m. - 5 p.m.
Enjoy some of the best breweries on the West Coast at the Fifth Annual Coastside Brew Fest, hosted by Mavericks Community Foundation. Guests will enjoy unlimited tastes of their favorite brews from vendors such as Alpha Acid Brewing Company, Altamont Beer Works, Barebottle Brewery, Deschutes Brewery, Drake’s Brewing Company, East Brother Beer Co., Faction Brewing, Fort Point Beer Co. This year’s beneficiary is the Mavericks Coastside Foundation, and a portion of the proceeds will be donated to Coastside Hope. Tickets are $30 in advance or $40 at the door; designated driver tickets are $10. Tickets are available at 390 Capistrano Road, (650) 728-2739.

3rd Annual Half Moon Bay Golf Links “No One Left Behind” Charity Golf Tournament

Oct. 28, 7 a.m. to 2 p.m.
In an effort to support firefighters and their families that are dealing with cancer and to educate others on how to prevent and detect cancer as best they can, Cal Fire Locals 2881- which covers the area from San Mateo to Santa Cruz- has partnered with Half Moon Bay Golf Links to host an annual golf tournament fundraiser. Golf participants are paired up with a current or retired firefighter and are treated to a shotgun format tournament on Half Moon Bay Golf Links’ beautiful Old and Ocean courses - two of the most scenic public golf courses in California. Golf will be followed by a full barbecue lunch, a reception, and comments from the Command Leader. To register, learn about sponsorship opportunities, and get more information about the event, visit or call (650) 464–2722. Half Moon Bay Golf Links, Two Miramontes Point Road. 

146th Anniversary Celebration Pigeon Point Light Station

Nov. 17, 1 p.m. – 7 p.m. (free!)
Perched on a cliff 20 miles south of Half Moon Bay, the 115 feet tall Pigeon Point Lighthouse and Historical Park is one of the tallest lighthouses in America and has been guiding mariners since 1872. During the 146th anniversary celebration, guests will enjoy live music, refreshments, face painting, native plant sales, a grounds tour, and more. From 5 p.m. – 7 p.m., the iconic First Fog Signal Building will remain open to show off the magnificent First Order Fresnel Lens. 210 Pigeon Point Road, Highway 1, Pescadero, (650) 879-2120,

2018 Colony of Coastside Artists Open Studios

Nov. 17-18, 10 a.m. - 5 p.m. (free!)
Art lovers will flock to the annual Open Studios for the chance to score that perfect piece of local work. Hosted by the Colony of Coastside Artists, nearly 40 local artists will open their homes and studios to the public for this once-a-year showcase of their work. Peruse and purchase paintings, drawings, sculpture, jewelry, hot glass, and much more. For more information, visit

Night of Lights

Dec. 7, 6 p.m. – 9 p.m. (free!)
Night of Lights is an annual old-fashioned holiday event hosted in downtown Half Moon Bay on the first Friday in December. Visitors will enjoy trees decorated in dazzling lights while doing some holiday shopping in the unique coastal shops. The event features a tree lighting ceremony in Mac Dutra Park, a Parade of Lights down Main Street, carolers and musical entertainment, roasted chestnuts and activities for the kids. For more information, visit our Night of Lights page. Main Street. 

Thanks to Chamberlin Public Relations for contributing event information to this article.

Kevin Henney is a web developer and photographer who can often be found behind the scenes of He's a sixth-generation resident of the Coastside, but never fails to find something new to experience in our little seaside towns.