Select Page
Los Gatos Fall Wine Walk

Los Gatos Fall Wine Walk

Los Gatos Fall Wine Walk 2015Save the date! The Los Gatos Fall Wine Walk takes place this weekend, Saturday, Oct. 14, 2023, from  1 – 4 pm, in downtown Los Gatos. Over 30 wineries will be participating!

Los Gatos Fall Wine Walk tickets are on sale now. Buy your tickets here.

Tickets are less in advance (more at the event, but it usually sells out). Loads of info on the Los Gatos Chamber of Commerce’s website, including the long list of participants. Prices will be updated once published.

Los Gatos Fall Wine Walk Details

All the details will be on the Chamber of Commerce’s website.

If you’ve never attended, this is the location:

Downtown Los Gatos, N. Santa Cruz Avenue & Main Street Los Gatos, CA 95030


Have fun at the St. Mary’s Country Fair in Los Gatos

Have fun at the St. Mary’s Country Fair in Los Gatos

St Mary's Country Fair - Stage and RideSt. Mary’s Country Fair in Los Gatos is a fun, annual community event that occurs in early October. This year it’s October 6 – 8, 2023.

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 6, 5 pm to 10 pm
Saturday, October 7, 10 am to 10 pm
Sunday, October 8, 10 am to 3 pm (earlier than in the past)

Hours for the Harvest Market Thursday Oct 5:

11 am to 4 pm no entrance fee
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.)

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!

Fiesta de Artes in Los Gatos – Los Gatos Art & Wine Festival

Fiesta de Artes in Los Gatos – Los Gatos Art & Wine Festival

Fiesta de Artes - Los Gatos Art & Wine Festival - painter and grapes and wineThe annual Los Gatos Fiesta de Artes is back. Now called the Los Gatos Art & Wine Festival, in 2023 it’s celebrating 51 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

Mark your calendars Sept 16 – 17, 2023 10 a.m. – 6 p.m.

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:


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

RIP Los Gatos Dammit Run – a COVID casualty?

RIP Los Gatos Dammit Run – a COVID casualty?

Click the image to visit the Dammit Run website!

The once annual Los Gatos Dammit Run used to take place in August, often early in the month, and the proceeds benefitted Los Gatos High’s track repair fund. The last one we heard of was the 47th annual run in 2019.  Like many things, it seems to have disappeared with the onset of Covid.

Here’s what we shared previously about the Dammit Run (the website is no longer active).

Beginning and ending at the track of Los Gatos High School, the 5 mile race takes participants through beautiful flatlands and hills. The treck includes the Los Gatos Creek Trail, the Jones Road Trail and a trip to the Lexington Reservoir dam (hence the name, Dammit Run). At the end, runners return to booths, raffles, refreshments, music and more on the Los Gatos High School campus.

In 2011, over 800 runners participated. To get all of the details, please see the website for the Dammit Run:


This is a bit of a bummer, but there are lots of opportunities to either run or support runners for a good cause. One is Steps4Smiles in Los Gatos, which happens on Aug 12, 2023, and ICC Sevathon at Vasona on Sept 12th.

More on Los Gatos events:

End of summer night ride and pasta dinner (Billy Jones Wildcat Railroad)


Los Gatos Celebrates July 4th, Independence Day, Join in the Fun!

Los Gatos Celebrates July 4th, Independence Day, Join in the Fun!

Los Gatos Celebrates Independence Day

It’s officially summer and Independence Day is fast approaching! What are your plans for the fourth?

For our family, it’s the annual 4th of July Symphony and celebration!

Independence Day, July 4th: Los Gatos Symphony in the Park!

4th of July Symphony in the ParkThe Town of Los Gatos celebrates Independence day with free music, food and fun at Oak Meadow Park on Tuesday, July 4th from 11am – 3:30pm.

There will be great American music, barbecue, beer, snacks, games, a few words shared, train rides on the Billy Jones Wildcat Railroad, rides on the historic carousel, and good fun for the family.

The San Jose Wind Symphony will come together once again, this year with a guest conductor Dr. Danielle Gaudry. This is the main feature, and their performance will begin at 1pm.

So take some friends, wine and a picnic, and enjoy your day at the park! Bring something to sit on, protect yourself from the sun, and prepare to have fun!

Remember, parking in Oak Meadow is free to Town residents, but spots are limited so carpool if you can and come early. If you’re willing to tackle a bit of a hike, there’s also limited street parking uphill from the park along University Ave. Oak Meadow walking paths also connect to Vasona Lake County Park where there is additional paid parking and a longer walk, but no hill to hike.

For more information, please see the info page on the town’s website for the July 4th happenings and the event flier.


Sounds of Summer Festival

Sounds of Summer Festival

Sounds of Summer festival Los Gatos 2023 - 3 bands, free concert!This Saturday is the all new Sounds of Summer Festival, which we mentioned in our long post about all of the free music offerings in Los Gatos this summer.

The Sounds of Summer Festival Details

This will take place Saturday, June 3, 2023, from 2 pm to 8:30 pm in downtown Los Gatos at the Civic Center lawn on Main Street. Three bands will be performing:

2:00  Gypsy Tribe, a Rumba Flamenco/Jazz Fusion band

4:00 Collectivity, a jazz/funk, psychedelic soul band

6:00 Houserockers, a 10 piece Rock & Soul group

Find more details on the Meetup website.