Festivals & Fairs

When: June 5-14, 2026 (except June 8-9)

Where: San Mateo County Event Center, San Mateo, CA

The Experience:

Ride carnival attractions and enjoy midway games, try fair food, and explore vendors and exhibits at this family-fun event. Watch live music, concerts, and performances (included with admission) and discover themed areas such as:

• Livestock/farm exhibits
• Kids and family zones
• Educational and creative exhibits (arts, robotics, etc.)

Highlights:

• Concert series and live entertainment stages
• Cultural celebration days (e.g., Pride Day, Pacific Islands Day)
• Unique exhibits (like themed attractions or science/tech displays)

When: June 5-6, 2026

Where: San Mateo County Event Center (as part of the fairgrounds)

The Experience:

The Bayside 101 Music Festival is a two-day live music festival that kicks off the San Mateo County Fair, featuring a mix of national headliners, local artists, and DJs across multiple stages and genres. You’ll see performances from DJ Bitesize, Dogpark, Gym Class Heroes, Hinder, Never Ending Fall, Radio Ready, and more!

Highlights:

• A drone light show after the main stage performances, featuring hundreds of synchronized drones creating animated light displays in the sky
• Access to fair food, drinks, and vendors throughout the event
• Admission included with general admission to the San Mateo County Fair (no separate ticket needed)

When: July 26, 2026

Where: Coyote Point, San Mateo

The Experience:

Heritage Fire is an all-inclusive, walk-around culinary experience that brings together top local chefs, restaurants, and food lovers to celebrate bold flavors and community. The event centers around chefs preparing dishes—often over open flames—showcasing unique, high-quality ingredients and culinary creativity. Guests enjoy a wide variety of thoughtfully crafted dishes and curated beverages while voting for their favorite bite of the day, ultimately awarding one standout chef the title of Heritage Hero. Throughout the national tour, winning chefs earn a place in the final competition, where top contenders gather at the Heritage Hero Grand Finale to compete for the ultimate title of Grand Champion.

Highlights:

• Live-fire cooking & bold flavors
• Curated drinks & full culinary experience
• Community-focused, multi-city tour

When: August 28, 2026

Where: Half Moon Bay Brewing Company, Half Moon Bay

The Experience:

Whiskies of the World is one of the premier whiskey-tasting event series in the United States, offering guests the opportunity to explore a wide range of exceptional spirits from around the globe in an immersive, educational setting. Designed for both seasoned connoisseurs and curious newcomers, the event brings together distillers, experts, and enthusiasts to deepen appreciation for whiskey through guided tastings, conversations, and discovery of diverse flavor profiles—from nose to finish. By showcasing expressions from local producers alongside international brands, Whiskies of the World creates a unique platform to celebrate craftsmanship, expand palates, and experience the rich variety of whiskey without ever leaving the room.

Highlights:

• Global whiskey tasting experience
• Educational, guided tasting journey
• Meet distillers & industry experts

When: September 5-6, 2026 | 10 AM – 5 PM

Where: Broadway Avenue, Downtown Millbrae (between Victoria Ave. and Meadow Glen Ave.)

The Experience:

The 55th Annual Millbrae Art & Wine Festival is one of the Bay Area's most beloved end-of-summer traditions, drawing more than 50,000 attendees to celebrate creativity, community, and the spirit of the Peninsula. Free to attend, the festival brings together local artists, live music, craft beer and wine tasting, gourmet food, and family activities all in the heart of downtown Millbrae. Whether you're a food lover, art enthusiast, or simply looking for a great way to soak up the season, this is one Peninsula experience you won't want to miss.

Highlights:

• 170+ artists and crafters showcasing jewelry, ceramics, glasswork, paintings, textiles, wood, photography, and more; beer, wine tasting, and artisan food from local and regional vendors
• Live music, interactive art workshops, kids' crafts and games, and community performers throughout the weekend
• Free admission for all attendees, with easy access via Caltrain and BART at Millbrae Station

When: September 26-27, 2026 | 10 AM – 6 PM

Where: Along Palmetto Ave in Pacifica, CA

The Experience:

The Pacific Coast Fog Fest is a long-running, free, two-day community festival held each September along Palmetto Avenue in Pacifica, celebrating the city’s coastal culture and bringing together locals and visitors. Originally founded in 1986 to promote Pacifica, it has grown into a beloved tradition featuring a lively kickoff parade, live music across multiple stages, and over 200 arts and crafts vendors. Visitors can enjoy a wide range of activities, including food and beverage booths, family-friendly play areas, contests, and community events just steps from the ocean. The festival emphasizes community spirit, with proceeds supporting local nonprofit groups and over $1 million raised to date. Designed for all ages, Fog Fest blends entertainment, local culture, and scenic coastal atmosphere into a relaxed, festive weekend experience.

Highlights:

• Lively parade & community traditions
• Live music and 200+ arts & crafts vendors
• Food, family fun & coastal atmosphere

When: October 17-18, 2026 | 9 AM – 5 PM

Where: Main Street in Half Moon Bay

The Experience:

The Half Moon Bay Art & Pumpkin Festival is a world-famous, free, two-day celebration held each October in downtown Half Moon Bay, known as the “World Pumpkin Capital.” It brings together thousands of visitors to celebrate the fall harvest with a vibrant mix of giant pumpkin displays, live entertainment, arts and crafts, and festive food. The event is closely tied to the Safeway World Championship Pumpkin Weigh-Off, where massive, record-breaking pumpkins are showcased as a central attraction. Festivalgoers can enjoy multiple music stages, a lively parade, family-friendly activities, and seasonal traditions like pumpkin carving and contests. Held along historic Main Street, the festival captures the spirit of autumn on the coast, celebrating local agriculture, community, and creativity in a fun, festive atmosphere.

Highlights:

• World Championship Pumpkin Weigh-Off
• Live entertainment & festive atmosphere
• Fall food, crafts & family fun