“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 County Fair
Aug 1-8
If you can’t find something to love at this hoedown hang—2024 tagline, “Barn to be wild”—it might be time to head on out to pasture. The live music lineup is legit, with artists like Uncle Kracker, Chicano All-Stars and Nzuri Soul Band headlining a dozen-plus music acts. The carnival rides are reason enough for a pilgrimage. The hypnotist and comedy circus performers feel like a bonus. The award-winning goats, pigs, cows and other creatures provide a kid-of-all-age-bracket favorite. Then there are Local Getaways’ all-time favorite MCF super stars: the All-Alaskan Racing Pigs. A most glorious hoof race if there ever was one.
More info: montereycountyfair.com
Festa Italia
Sept. 6-8
You know you’ve got something good going when your event has happened annually since…Prohibition was legal. At the 91st 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 calamari cooking demo illuminates foodies and a range of seasoned paisanos fill the air with song: Internationally renowned Pasquale Esposito, 831 All Star Band, 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.
More info: festaitaliamonterey.org
Michael Feinstein in a Tribute to Tony Bennett at Sunset Center
Sept. 13
Sometimes you gotta let the accomplished curators of entertainment at Sunset deliver their message unvarnished: “Following the program’s sold-out debut at Carnegie Hall, entertainer extraordinaire Michael Feinstein is taking the Carnegie Hall Ensemble back on the road for the national tour of Because of You: My Tribute to Tony Bennett. With tunes made famous by Feinstein’s close friend—including “Because of You,” “I Left My Heart in San Francisco,” and “New York State of Mind”—this concert celebrates the songs and stories of the legendary Bennett, whose career spanned more than seven decades and resulted in what Feinstein calls ‘a body of work surpassed by none.’” Enough said, and a lot to look forward to.
More info: sunsetcenter.org
Carmel Valley Gem and Mineral Show
Sept. 21-22
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?”
More info: cvgms.rocks
GridLife Laguna
Sept. 27-29
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 performance driver education, the final round of the NOS Energy TrackBattle Time Attack, and—oh yes—full-course drifting. Off track, multiple live concerts headline, plus a simulator arcade, concours displays, food vendors, and camping.
More info: gridlifelaguna.com
Northern California Renaissance Faire
Weekends Sept. 14-Oct. 20
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 “Oktoberfest”; non-stop entertainment across multiple stages, including live music, comedy acts, and jousting tournaments; and an Artisan Marketplace with 200+ master creators.
More info: norcalrenfaire.com
Monterey Jazz Festival
Sept. 27-29
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 Herbie Hancock, Mavis Staples, Thundercat, Dianne Reeves, Snarky Puppy, and Samara Joy. Additionally, the festival will showcase performances by Cory Henry & The Funk Apostles, Hiromi’s Sonicwonder, and the SFJAZZ Collective, celebrating their 20th anniversary. The Blind Boys of Alabama, Stanley Clarke N•4EVER, and Robert Glasper too. The longest running of its kind doesn’t do half way.
More info: montereyjazzfestival.org
California International Airshow
Sept. 27-29
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.
More info: salinasairshow.com
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!
