Located about 30 miles south of San Francisco on CA-1, Half Moon Bay is a charming small town with several shops and art galleries, many of which line Main Street a block east of the CA-1 bypass. Half Moon Bay enjoys a beautiful natural setting and earns significant income from tourism, especially during an intense winter surf competition, and the world-famous pumpkin festival each October.

Visit the Half Moon Bay Chamber of Commerce (235 Main St., 650/726-8389, 9am-5pm Mon.-Fri., 10am-3pm Sat.-Sun.), in the red house just after you turn on Main Street from CA-92. The chamber doubles as a visitors center, where you can find maps, brochures, and a schedule of events.

Rocky coast near Half Moon Bay

Rocky coast near Half Moon Bay. Photo © Morozova Tatiana/123rf.

Titans of Mavericks

The beaches of Half Moon Bay draw visitors from over the hill and farther afield all year long, despite the chilly fog during the summer. Perhaps the most famous beach in the area is one that has no name. At the end of West Point Avenue in the neighboring town of Princeton is the Pillar Point Marsh and a long stretch of beach that wraps around the edge of the point. This beach is the launch pad for surfers paddling out to tackle the infamous Mavericks Break (Pillar Point Marsh parking lot, past Pillar Point Harbor).

Formed by unique underwater topography, the giant waves are the site of the legendary Titans of Mavericks surf contest. The competition is always held in winter, when the swells reach their peak, and left until the last minute to ensure that they are the biggest of the year. When perfect conditions present themselves, the best surfers in the world are given 48 hours’ notice to make it to Mavericks to compete. Unfortunately, you can’t see the breaks all that well from the beach, but there are dirt trails that crisscross the point, where breathtaking views can be had. Walk up West Point Avenue past the yellow gate and catch any number of dirt trails heading west toward the bluffs. But for those eyeing the big waves, beware: Mavericks is not a beginner’s break, especially in winter, and the giant breakers can be deadly.

The biggest annual event in town is the Half Moon Bay Art & Pumpkin Festival.

The biggest annual event in town is the Half Moon Bay Art & Pumpkin Festival. Photo © snyfer/123rf.

Half Moon Bay Art & Pumpkin Festival

The biggest annual event in this small agricultural town is the Half Moon Bay Art & Pumpkin Festival. Every October, nearly 250,000 people trek to Half Moon Bay to pay homage to the big orange squash. The festival includes live music, food, artists’ booths, contests, activities for kids, an adults lounge area, and a parade. Perhaps the best-publicized event is the pumpkin weigh-off, which takes place before the festivities begin. Farmers bring their tremendous squash on flatbed trucks from all over the country to determine which is the biggest of all. The winner gets paid per pound, a significant prize when the biggest pumpkins weigh over 1,000 pounds.

Excerpted from the First Edition of Moon Pacific Coast Highway Road Trip.