Monterey Events in September: Festivals, Wine Tasting, and More Things to Do

Jill on a windy day at the Golden Gate Bridge

by Jill Loeffler  •

Updated: August 4, 2021

Discover a full calendar of the best Monterey events in September 2021. My guide includes options all around the bay including Santa Cruz, Salina, Carmel-by-the-Sea, and others.

Monterey Events in September

Top picks this month include the Monterey County Fair, PURE Insurance Championship at Pebble Beach, and the Capitola Art & Wine Festival.

Disclaimer: I receive a small commission from some of the links on this page.

Firestone Grand Prix of Monterey

Dates: 9/17 - 9/19

Location: WeatherTech Raceway Laguna Seca

This is the IndyCar fan's dream event as it is the final race that will award the driver, and his team, the open-wheel series crown for 2021.

Some of the best in the world have raced here, and this year will be no exception. You will want to plan ahead and make sure to get close to the action, so you hear the roar of the engines and feel the blast of air as these cars speed along the track.

Monterey County Fair

Dates: 9/3 - 9/6

Location: Monterey Fairgrounds

The annual Monterey County Fair offers live music, family entertainment, and more. All performances are free with admission tickets.

Check out some of the events, such as farmers showing off their livestock and the Jr. Livestock Auction. There are also carnival rides and more fun for kids of all ages

Click the link below for more information. It's one of the top Monterey events in September.

>> Visit their site for a full schedule and more details

Santa Cruz Greek Festival

Dates: Friday, 9/10 - Sunday, 9/12

Location: Prophet Elias Greek Orthodox Church at 223 Church Street, Santa Cruz

This festival celebrates everything special about the Greek culture and its people. You will enjoy music, dancing, events, and more when you attend this three-day festival. It is almost always voted the "Best Street Festival in Santa Cruz County."

You can shop at the agora and find beautiful Greek Jewelry, pottery, and much more. And what Greek Festival would be complete without loads of great Greek food such as Souvlaki, Gyros, Baklava and more.

If you don't know what those are, or haven't tasted them before, then this is a can't miss celebration for you. Don't miss out as this is one of the best Monterey events in September every year!

All ages are welcome, and admissions is free all three days.

Flavors of Pacific Grove

Date: 9/30

Location: Various locations

Times: 5:30 pm to 8 pm

Cost: $60.00

One of the wonderful Monterey events in September includes this fun and charitable event at the Pacific Grove Gold Club House. Each year there are over 120 donations auctioned off that include golf packages, accommodations, trips, and restaurant certificates, among others.

In addition to the auction there are a number of the best chefs that work in Pacific Grove and the Pacific Grove Golf Club House that will make sure to please your palate with their most delicious delicacies. There will also be live entertainment.

This is a truly beloved event every year and tickets usually sell out in advance, so it is best to purchase them as early as possible.

Festa Italia

Dates: Friday, 9/10 - Sunday, 9/12

Location: Custom House Plaza

This annual event celebrates the Italian culture and its history in the city of Monterey. It's a three-day event at the Custom House in downtown Monterey. It includes entertainment, raffles, a bocce tournament, a parade, Italian food and more.

There is an opening mass at the San Carlos Church and then the parade starts at 12 noon. It begins at 500 Church Street and continues through Downtown Monterey ending at the festival's location at the Custom House Plaza.

One of the local favorite events is the blessing of the fleet directly following the parade.

Admission is free.

Fun Activities Around the Monterey Bay

In addition to these top-rated Monterey events in September, you will also find other fun things to do throughout the month. These are just a few of my favorites.

Monterey Bay Aquarium: My first recommendation for the Monterey area is always the aquarium. This amazing attraction is consistently voted as one of the best aquariums in the world. Step inside to learn more about the hundreds of species of plants and animals that call the Monterey Bay home. Pick up advanced tickets so you don't have to wait in line.

Half-Day Whale Watching Cruise: Head out on the water in search of whales this September in Monterey. This cruise lasts about three and a half hours and offers you the chance to learn all about some of Monterey's most popular guests. This time of year, you are most likely to see Humpback and Blue Whales as they migrate through the area. You will also want to be on the look out for birds, dolphins, sea turtles, and other local animals. Find out more about this tour.

E-bike Tour: Another fun option for September is to ride around the bay area on an ebike. This tour includes a cruise along the beautiful 17-Mile Drive. Your tour starts with a brief training on your ebike, so all riders are comfortable before you leave. You will then explore several locations along 17-Mile Drive including John Denver Memorial, the Point Pinos Lighthouse, & Asilomar Beach. Your ebike will allow you to go further and faster, so you can see more. Learn more and reserve your spot on this tour today.

Mole & Mariachi Festival

Date: TBD for 2021

Location: Santa Cruz Mission State Historic Park at 144 School Street

Head over to the Santa Cruz Mission State Historic Park for this one-day festival that celebrates culture, food, and so much more. During the event, you can enjoy live music, dancing, and dozens of exhibits.

The event runs from 11am to 5pm. Proceeds go to the nonprofit Friends of Santa Cruz State Parks in support of Santa Cruz Mission State Historic Park.

If you are a lover of Latin culture, food, and dance, you will definitely want to check out this festival. It's one of the top Monterey events in September.

Monterey Jazz Festival

Dates: Friday, 9/24 - Saturday, 9/26

Location: Monterey County Fairgrounds

Heading into its 64th year, the Monterey Jazz Festival is the longest running jazz festival in the country. Routinely known as the best jazz festival in the USA, and possibly the world, this is a can't miss event.

Even though it is labeled as a jazz festival, this massive musical gathering also includes soul, rock and roll, hip hop and much more.

This year's event will once again feature top named artists such as Herbie Hancock, The Roots, and Gary Clark Jr.

There are different packages for tickets, so be sure to check the link below and find just the right one for you.

>> Visit their site for this year's schedule and ticketing information

Oktoberfest Monterey Bay

Date: Saturday, 9/4

Location: Monterey County Fairgrounds

Drink German beer and dance to fun tunes at this year's Monterey Bay Oktoberfest. Live music this year is provided by The Internationals Band. You can also enjoy family friendly activities such as the Dachshund Races, a petting zoo, and jump houses.

Some of the fun games and events include the Beer Stein holding contest, Miss Junior Oktoberfest and Miss Oktoberfest. This is why it's one of the must attend Monterey events in September.

If you really want to get in the Oktoberfest spirit, make sure you yell, "Ziga Ziga! Oi Oi Oi!" with the others are you celebrate with a brew or two in the beer gardens!

Santa Cruz County Fair

Dates: Wednesday, 9/15 - Sunday, 9/19

Location: 2601 East Lake Avenue, Watsonville

This fair has been going on for over 100 years and just continues to get better and more exciting. For seven full days, experience carnival rides, magicians, animal acts, pet shows and so much more including the fan favorite tractor parade.

Attendees love the horse show and the skill and beauty of the horse and rider as they move around the ring. There are lots of exhibits and vendors selling all types of goodies.

There will be lots of events for kids, and adults, since this is an all ages event. Last but not least, there is live music during the event during the daytime and at night.

Check the link below for schedule and ticket prices.

>> Visit their site for more information

PURE Insurance Championship Impacting The First Teeat Pebble Beach

Dates: Monday, 9/20 - Sunday, 9/26

Location: Pebble Beach Golf Links and Poppy Hills Golf Course

This is one of the best golf events if you want to see pros, amateurs and juniors from all over the world. This is a 3-day and 54-hole tournament that is widely regarded as one of the most prestigious, and beautiful, in the world.

Some of the players that have attended, or will attend, this event includes Mark Calcavecchia, Fred Couples, Lee Janzen, and many other famous golfers. The amateur round includes 81 teams of two players each.

Juniors aged 15 to 18 years old, from all over the US will also compete at Pebble Beach Golf Links. You will also get to see many legendary golfers as they help mentor these up and coming athletes. This is one of the great Monterey events in September for golf lovers.

>> Visit their site for more details and ticketing information

Capitola Art & Wine Festival

Date: TBD for 2021

Location: Stockton Avenue and Esplanade in Capitola

This fantastic 2-day event will let you experience the best of food, wine, art, and music from the Santa Cruz area. The city of Capitola hosts this event and overlooks the Monterey Bay which offers amazing views all along the festival.

Some of the fun events you will find here include checking out pieces from the over 160 artists, tasting delicious wine from the over 20 wineries, and eating fantastic food made by local chefs with local foods.

There will also be great entertainment for the whole family including live music and exhibitions by street performers, dance groups, and more.

Prices and time depend on event. Please check the link listed below to find out specifics.

>> Visit their official site for details

Aloha Polynesian Festival and Outrigger Races

Date: Sunday, 9/19

Location: Municipal Wharf in Santa Cruz

The annual Aloha Polynesian Festival and Outriggers Races will once again be held at the Municipal Wharf in Santa Cruz. Cheer on the competitors as they race their way to the finish line during the Outriggers Races.

You can also sample tasty traditional Polynesian treats, shaved ice and drinks all day long. Vendors will line up along the Wharf so you can cheer on the races as you enjoy some tasty treats.

The event runs from 1pm to 5pm.

>> Visit their site for full details

Boardwalk Bites & Brews

Date: TBD for 2021

Location: Santa Cruz Beach Boardwalk

This one of the great Monterey events in September that gives you the chance to walk around the gorgeous boardwalk, enjoy the rides there, and all while drinking great brews and eating some delicious bites!

One of the favorite events for beer and food lovers is the "Best Pairing" competition. Some of the foods range from chocolate covered bacon (don't knock it until you try it!), tacos, and other foods with the best locally produced beers.

There will also be live music and other events. Check the link below to learn more about the event, ticket prices and schedule.

>> Visit their site for details

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