10 Best Festivals and Events in Monterey

Did you know that the world’s longest continuously-running jazz festival is held in Monterey, California? That’s right – for more than 60 years the Monterey Jazz Fest has celebrated the heritage of jazz music.

Held annually in September, the weekend’s festivities include live performances on 5 stages all day long. Bands and solo acts flock to Monterey from around the world. Local food and drink vendors set up at the Monterey Fairgrounds where the festival is held to keep festival-goers fuelled for the lively festivities.

Calling all car enthusiasts to Monterey Car Week – where racing cars, vintage cars, muscle cars, and souped-up sports cars are on display in city centre Monterey. Each day, different car and driver categories come together for special shows like the Prancing Ponies Women’s Car Show or the Porsche Monterey Classic.

Don’t miss the opportunity to look through vintage car memorabilia on display or pop by an auction if you want to shop for a one-of-a-kind ride. Car Week happens annually in August.

Watch professional golfers and celebrities take to the green at the AT&T Pebble Beach National Pro-Am with proceeds from the PGA tournament benefitting local charities. The event, which can be spectated in person or on TV, takes place across 3 of Monterey’s top courses: Pebble Beach Golf Links, Spyglass Hill Golf Course, and Monterey Peninsula Country Club Shore Course.

Spectators can enjoy an array of activities besides just golf, including food trucks, wine gardens, a speakeasy, and upscale lounges with views of the courses. The tournament happens annually in winter.

California vibes run deep through the California Roots Music & Arts Festival, where hip-hop and reggae are celebrated en masse. The festival is large and hosts up-and-coming performers as well as chart-topping headliners.

Cali Roots is hosted on the Monterey County Fairgrounds. Festival goers get access to 3 stages, multiple bars, and concert merch. VIP packages with reserved viewing areas, plus a separate lounge and bar are available – which can be a great benefit since the festival hosts upwards of 10,000 guests per day.

The Monterey County Fair is a huge event spanning 4 days held on the 22-acre Monterey County Fairgrounds. The weekend festivities include a carnival with amusement park rides provided by Helm and Sons Amusement, live music on the main stage, and agriculture-related competitive exhibits.

From food and wine to arts and culture to games and experiences, the Monterey County Fair showcases the best that Monterey has to offer and there’s something that everyone in the family will enjoy.

Runners of the Big Sur International Marathon have the opportunity to see a large swath of California coastline on this point-to-point course. The race starts at Big Sur Station, runs along the scenic byway, and finishes 26.2 miles north in the city of Carmel, just shy of Monterey.

For those looking to enjoy the beauty of the course without the commitment of marathon training, shorter distances are also options (5K, 12K, 11-miler, 21-miler, and marathon relay). And if you want to make your running experience a bona fide holiday, there is a marathon tour package that includes lodging with your race registration.

The historic Monterey Wine Festival is a two-day event that pays homage to the humble grape with a vast array of vino tastings from award-winning vineyards. Sample chowder, calamari, and decadent cheese and charcuterie boards from esteemed West Coast chefs while sipping Cabernet Sauvignon, Moscato Spumante, Merlot, and rosé.

Held in the picturesque coastal town of Carmel-by-the-Sea, visitors will enjoy over 100 world-class wines from across Monterey County including Arroyo Seco, San Antonio Valley, and the Santa Lucia Highlands. After you’ve indulged, listen to live jazz music, peruse works by local artists, or get up close and personal with raptors at Green Fields Falconry.

The Monterey Scottish Games and Celtic Festival is an unforgettable summer weekend filled with music, living history, food, and whisky tastings. For more than 50 years, the Monterey Scottish Games and Celtic Association has been putting together this experience.

A competitive spirit runs throughout the festival with drum major contests, pipe band competitions, sheep dog trials, and Highland athletic events. Kids, too, will have a blast learning some of the Highland athletic skills, playing mini golf, or getting their faces painted.

Every year, festival-goers descend upon the historic Lighthouse Avenue to gather for the Good Old Days Street Festival. The free event is Monterey County’s largest annual arts and crafts gathering. The community event also has live music, dancing, carnival rides, a parade, and a petting zoo.

Don’t miss the wine and beer garden after grabbing a bite to eat at one of the numerous food booths. Overall, it’s a weekend full of community and traditional American festival fun, reminiscent of the good old days.

The Old Monterey Marketplace is like a festival held year-round. Every week the farmers’ market has exciting vendors selling local fruits and veggies and culinary treats with international influence. Think European pastries, Korean BBQ, or Mexican street food.

What you’ll find here changes week after week. A visit in the winter means you’re likely to find Christmas carol singers serenading the street. A visit in spring means you might find seed starts to get your own vegetable garden going. The beauty of Old Monterey Marketplace is in the variety of each visit.