“Life is a lot like jazz…” George Gershwin once said. “It’s best when you improvise.”
That applies at Monterey Jazz Festival, fittingly enough.
It’s good to have a plan going in, but many of the most meaningful and memorable moments can come about in an unplanned way.
That might be moving from stage to stage, being in the right place for the right surprise collaboration between appearing artists or running into fellow jazz fans. (See below for more info on 2024’s headliners.)
Same goes a visit to the Peninsula at this time of year.
As some of the best weather of the year lands in September, it’s advisable to come in with a plan, maybe anchored by one of the events below—but also with a willingness to go with the flow.
Featured Photo: Jens Thekkeveettil
Monterey
September 1
Monterey
If you can’t find something to love at this hoedown hang — 2025 theme, “Surfin’ Safari” — it might be time to head on out to pasture. The live music lineup is legit, with artists like The Cheeseballs and Jimmy Becker headlining a dozen-plus music acts. The carnival rides are reason enough for a pilgrimage. The hypnotist and magic show feel like a bonus. The award-winning goats, pigs, cows and other creatures provide a kid-of-all-age-bracket favorite, especially with their All Creatures Barnyard Racers act throughout the grounds. A most glorious race if there ever was one.
September 5-7
Monterey
You know you’ve got something good going when your event has happened annually since…Prohibition was legal. At the 92nd edition of Festa, authentic Italian music, dancing and cuisine—eggplant parmesan, steak-and-sausage sandwiches, pasta, arancini, pizza and cannoli—fill historic Custom House Plaza in the heart of Monterey. Meanwhile, a cioppino cooking demo illuminates foodies and a range of seasoned paisanos fill the air with song: Internationally renowned Pasquale Esposito, Mike Marotta, Jr. and Friends, tenor Erasmo Aiello, the Anthony Lane Band, Money Band and Tarantella Dancers all entertain. The collectible Italian merchandise awaits for any down time.
September 26-28
You could argue this one event would be enough to make September a destination month in Monterey. This year headliners include jazz legends such as Gregory Porter, Christian McBride & Ursa Major, Dianne Reeves, Ledidsi, Mr. Sipp, and Christian Sands. Additionally, the festival will showcase performances by René Marie & Experiment in Truth, Pete Escovedo feat. Juan and Peter Michael Escovedo. The U.S. Navy Band Commodores, Miranda Pearl, Paul Contos, Chris Cain, Grace Kelly, and the Arturo O’Farrill & The Afro Latin Jazz Ensemble. The longest running of its kind doesn’t do half way.
September 26-28
Salinas
From its roots in the American Midwest, GridLife can now claim valid coast to coast cred with its return to WeatherTech Raceway Laguna Seca for the final festival of the season, and the last races of the year for GridLife Touring Cup club race series. On track, the action includes the fastest Time Attack cars in the world, hair raising wheel to wheel racing with GLTC, and—oh yes—full-course drifting down the corkscrew! Off track, multiple live concerts headline, plus a simulator arcade, concours displays, food vendors, and camping.
Carmel
September 20 and 21
Let’s rock out. And get into gems, minerals, jewelry fossils, demonstrations, silent auctions, snacks, kid activities and equipment booths too. The Carmel Valley Gem and Mineral Society is a nonprofit dedicated to promoting the study of mineralogy and geology; to encourage the collecting of specimens and the practice of the lapidary arts; to promote field excursions to mineral locations and further the education of all. So they get it when Jane Austen asks: “What are men to rocks and mountains?”
San Benito
Every Weekend Starting September 13
Most months, San Benito County, California—the low-key neighbor to Monterey and Santa Cruz counties—is known for great barbecue, under-the-radar wine country and cattle. Come early fall, it’s known as the Elizabethan village of Willingtown, as the expansive Ren Faire transforms place and people alike. Key highlights include: themed weekends like “Pirate Invasion” and “Cottagecore”; non-stop entertainment across multiple stages, including live music, comedy acts, and jousting tournaments; and an Artisan Marketplace with 200+ master creators.
October 4-5
That roar in the sky above is the only reason you can’t hear your heart thumping out of its cockpit. The U.S. Air Force Thunderbirds star, joined by the U.S. Patriots Jet Team, Jon Melby in his Pitts S1B, Brad Wursten’s MX2 aerobatics and the Sukhoi West Demo Team. Closer to Earth, the “Wall of Fire” display and Smoke-n-Thunder Jet Car throw sparks. Attendees can also look forward to the KC-135 Stratotanker refueling demo, P-51 Warbirds, a dueling performance between Melby and Wursten, and even a lucha libre wrestling exhibition by the Empire Wrestling Federation.
Event Venues
Looking to see what’s happening right now on the Monterey Peninsula? Our comprehensive list of venues across the city below will help you find what you need to know what’s going on.
Looking for more things to do in the area?
Visit our What to Do in Northern California page!