by Mary Pope-Handy | Oct 1, 2026 | Los Gatos Events
St. Mary’s Country Fair in Los Gatos is a fun, annual community event that occurs the first weekend in October. This year it’s October 2 – 4, 2026.
Each year it’s a little different, a little better.
Open to everyone, and with no admission fee, the three day fundraiser is a great place to enjoy so many cool things, including:
- Butler Carnival rides (separate tickets)
- bouncy house
- country store shopping
- arts & crafts (such as pumpkin decorating)
- martial arts displays
- dancing
- dining (good and affordable!) – several food booths to choose from
- raffle
- play games
- giant slide
- full service coffee shop
- margarita booth
- talent show
- live bands
- bingo (of course!)
- Harvest Market
Hours for the St. Mary’s Country Fair:
Friday, October 2, 5 pm to 10 pm
Saturday, October 3 11 am to 10 pm
Sunday, October 4, 10 am to 3 pm (same as last year)
Hours for the Harvest Market Thursday Oct 1:
11 am to 4 pm free admission!
Evening Shopping from 5 pm to 9 pm $20 entrance fee
Shop, Appetizers, Drinks, Raffle & Music
Tickets presale or at the door
See even more at the event’s website.
This is a fabulous place to walk through and simply bump into friends & neighbors from all over Los Gatos and the nearby communities. It’s also a fun place to take photos. Each day is a little different, some return again and again!
Location details on the St. Mary’s Country Fair:
St. Mary’s Church and School are located in downtown Los Gatos on Bean Avenue near Tait (and near North Santa Cruz Avenue) in the historic Almond Grove neighborhood. You can also reach the party by co-To get all the details on the hours, booths, events, please check the (new) event website for all details
Extra tips:
Like a bargain? There’s an easy way to save money. Visit the parish or school office before Friday at 2pm and buy your Butler ride tickets at a substantial discount – and avoid the lines! (Tickets are sold in the 2 weeks leading up to the fair most years.) In 2025, advance tickets can be purchased at a discount until Sept 29th at the event’s ticketing site!
Also, much of the Almond Grove District of Los Gatos has permit parking only in the evenings. So don’t park in the neighborhood! There are lots of public parking spaces between North Santa Cruz and University Avenues in Los Gatos, and they are no cost, so park there instead. I usually like to park between North Santa Cruz Avenue and University Avenue in the public lot. If you’re in biking distance, consider cycling in – just remember lights are required when biking in the dark, and remember road safety!
by Mary Pope-Handy | Sep 20, 2026 | Events, Los Gatos Events
The Los Gatos Concert Association’s season is underway, again bringing delightful music to our town from fall through spring. “A first class concert series at affordable prices” is the goal, and by all accounts it is consistently successful at it. The first concert debuts on Sept 23rd and tickets for the series are open to the public for purchase. Tickets are on sale as a season pass covering all four shows and cannot be bought individually for each concert except when there is availability at the door and online shortly before the event.
What’s on the agenda for this season? (We’ve missed the first one, but three remain.)
Please get ALL of the details and purchase tickets via their page: https://lgcca.org/2026-2027-season-concerts/
All performances are at Los Gatos High School. For more info on musicians, times, ticket pricing, discounts for seniors and students, as well as subscription pricing, please see the LGCCA website.
by Mary Pope-Handy | Sep 3, 2026 | Events, Los Gatos Events
The annual Los Gatos Fiesta de Artes will be Sept 26-27, 2026. Now called the Los Gatos Art & Wine Festival, this year it’s celebrating 54 years of art and entertainment in downtown Los Gatos. (It returned in 2021 after being canceled in 2020 due to the pandemic.)
Fiesta de Artes, Los Gatos Art & Wine Festival dates & quick info
Mark your calendars Sept 26 – 27, 2026 10 a.m. – 6:30 p.m. on the Civic Center Lawn.
Yes, you can bring your dog!
If you’ve never been, it’s a fabulous opportunity to mill around the Civic Center lawn and enjoy art of various types. It’s free! If you’d like to partake of food and wine, the proceeds all go to a very good cause. And of course, there are plenty of beautiful art pieces for purchase, too.
What happens at the Fiesta de Artes or the Los Gatos Art & Wine Festival?
Think food & drink, art & shopping, dancing & socializing! Once again, there will be more than 150 vendors with a huge variety of artists and vendors displaying and selling their artwork, plus booths with food and wine and of course loads of music throughout both days. Please check out the musical lineup and food offerings info here: Fiesta music and food
Fiesta de Artes will be at the Civic Center lawn across the street from Los Gatos High School – 110 E Main Street, Los Gatos CA 95030
Patrons are encouraged to bike, walk, carpool, use public transportation or get friends and loved ones to drop you off. Apparently there’s even a bike valet to facilitate arriving on two wheels. (Per the FAQ page, which is loaded with great information.)
Many thanks to the Kiwanis Club of Los Gatos and all of the other sponsors for making this wonderful event possible yet again.
Please check out all of the details at the event’s website:
https://losgatosfiesta.com/
Related reading:
Los Gatos Spring Wine Walk (there’s usually a Fall Wine Walk in October, too)
Los Gatos Free Music Concert Series
Los Gatos Youth Theatre Summer Musicals
by Mary Pope-Handy | Sep 1, 2026 | Dining, Events, Los Gatos Events
The annual Los Gatos Lions Date Night event will be held Campo Di Bocce, Los Gatos. Enjoy the evening of wine, brews, and food tasting provided by 11 local premier wineries and breweries, and 11 premier restaurants and specialty places. The event features a raffle, Silent Auction of great items, a Live Auction of a few very select items and live music. This is a sell out event, so buy your tickets soon!
Los Gatos Lions Date Night details
When: Sunday, Sept 13, 4 – 7 p.m.
Where: Campo di Bocce of Los Gatos, 565 University Avenue Los Gatos, CA 95032
Cost: $100 per ticket ($108.55 as there’s a service charge added)
This fundraising event at Campo di Bocce provides much-needed financial support to our Los Gatos Schools’ mental health initiatives and student counseling services. The benefactors in years past were: Los Gatos High School, RJ Fisher Middle School and CT English Middle School.
Date Night always sells out and tickets will not be available at the door.
For more info: https://e-clubhouse.org/sites/losgatos/page-8.php
Buy tickets here.
by Mary Pope-Handy | Aug 8, 2026 | Events, Kids, Los Gatos Events
Each August, the Billy Jones Wildcat Railroad and W.E. “Bill” Mason Carousel host their End of Summer Night Ride, a pasta dinner fundraiser!
End of Summer Night Ride details
Typically this event is held near the end of the month, however this year it will be held Sunday, Aug 9, 2026 from 6 PM – 8:45 PM.
At the very end of the summer season, the railroad and carousel hold their second major fundraiser of the year – the End of Summer Night Ride and Pasta Dinner. Evening activities begin at 6 PM, and the last train departs at 8:30 PM. You can purchase by the ride ($7 for train, $5 for carousel), one combo train and carousel ticket, for one ride on each, at $10, or get the unlimited pass (sold per person) and ride as many times as you want all evening for $20 per person.
Remember that children 2 and under ride free with paying adult.
Dinner is served from 6 – 8 PM, and a donation of $15 per adult and $11 per child will get you a plate piled high with spaghetti and meat sauce, a garden salad or caprese, and garlic bread. Vegetarian options are available, and beverages are an extra fee (beer and wine will be available for purchase). Additional donations are always welcome.
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by Clair Handy, Mary Pope-Handy | Jul 25, 2026 | Events, Irrelevant Fun, Kids, LG Lifestyle, Los Gatos Art & Entertainment, Los Gatos Events, Los Gatos History, Parks, Visiting Los Gatos
This weekend enjoy some family-friendly fun and local history at Oak Meadow Park with back-to-back celebrations for National Carousel Day and Billy Jones Day!
National Carousel Day: July 25th
Today, Saturday July 25th 2026, is National Carousel Day! To celebrate, take a ride on the historic (and beautifully restored) W.E. “Bill” Mason Carousel. Come learn about the history of this centenarian ride from carousel volunteers, or just enjoy the music of the band organ, the lights, the art, and festivities. Did you know that each horse has a name? Not only that, you can learn a little about each horse (or even adopt one) by visiting the Carousel Horses page on the Billy Jones Wildcat Railroad website.
Hear a little more about what to expect from Will Whitney here: https://fb.watch/IAOlcNzb5Z/ And adults and older kids may enjoy reading about the preservation project, covered in this Los Gatan article by Amanda Senior earlier this year: In the workshop with carousel restorer Cheryl Stuermer.
Billy Jones Day: Last Sunday in July
The last Sunday of July is Billy Jones Day, also this weekend on July 26th! This annual celebration “honor[s] the man who started it all by doing things the way he did on his ranch.” (BJWWR) That means all rides (on both the train and carousel) are an open donation instead of their usual fee – donate as much or as little as you like to support the nonprofit, Billy Jones Wildcat Railroad, Inc., that is keeping these rides running and open to the public, and preserving them and their history for the next generation.
This year they’re going full-steam ahead and firing up all the locomotives plus one guest steam enegine for the event!
Both days, the train and carousel will be on their usual summer weekend hours, running from 10:30am – 4:30pm. The Snack Shack will be open both days from 11:00am – 3:30pm. There may be a fee of $6 to park at the Oak Meadow Parking lot if there is an attendant at the booth, however the lot can fill up early on summer weekends, so plan accordingly!
