The Kiwanis Club of Los Gatos has been running the Art & Wine Festival on the Civic Center Lawn since 1971. Fifty-five years in, the pours, the crafts, and the two-day September window on Main Street are close to what they were a decade ago. What is not the same is the block you walk to get there. Between the last Art & Wine weekend and this one, the downtown storefronts that residents actually move through between festival stops have quietly turned over. If you have not eaten downtown since spring, your Saturday is going to feel different even if the tent map does not.
This post is for the people who already live here. It is a walk-through of what has changed, where it sits, and how to string the two anchor weekends of the season together without ending up back at the same three restaurants you were choosing between last fall.
The two dates worth holding
The season's fixed points are close together this year. OktoberfestLG returns to downtown on Saturday, September 19, at 12:00 PM. One week later, the Los Gatos Art & Wine Festival takes over the Civic Center Lawn at 110 E. Main Street on September 26 and 27, from 10:00 AM to 6:30 PM both days. The festival is a Kiwanis benefit, with proceeds funneled back into local scholarships, leadership clubs at the schools, and Pediatric Trauma Prevention support at the children's hospitals, so the money you spend on a wine pour is doing double duty.
Between and around those two Saturdays, the Los Gatos Sunday Farmers' Market at Town Plaza runs 9:00 AM to 1:00 PM, rain or shine. That is the connective tissue of the fall calendar. Once you know it is there every week, the two festival weekends stop feeling like isolated events and start feeling like the peaks in a rhythm.
What actually changed on the block
Here is the short version of the storefront turnover you will notice on the walk from the Civic Center up N. Santa Cruz Avenue and back down Main.
- Heritage Pub and Chop House opened on the second story of the La Cañada Building, a space that had sat vacant for seven years after the closure of Los Gatos Bar & Grill. Owners Walker and Kristi Pearce-Percy, both Los Gatos natives, worked with Executive Chef Yvonne Khananis on a menu that pulls from Irish, English, and Scottish pub cooking alongside American classics. There is a banquet room, a game hall with shuffleboard, and outdoor seating that brings total capacity to 180.
- Petals Creamery opened this summer on the ground floor of the same La Cañada Building.
- Second Story, in the same building, opened late last year.
- Dar Restaurant and Bar opened downtown this spring from brothers Milad and Chef Esam Shaqir, whose Saturday-night crowd already knew them from Saratoga. Their Los Gatos concept is more elevated than the Saratoga original, with a menu drawing from the Levant, Italy, and Morocco, a full bar, and a large patio with a fireplace.
- 25 E. Main Street, which most recently housed Sidecar Modern Tavern, is being taken over by chef Coskun Abik for a Greek-Anatolian restaurant. Abik, whose Bay Area résumé includes Blind Butcher SF, Dunya Bistro, and Moka Coffee SF, signed a lease that started at the beginning of August. His menu leans on Maras pepper, oregano, and olive oil, which he describes as a lighter register than the Arabic-influenced flavors at Dar.
Two more names are on the way and worth knowing so you can watch for the signage:
- Vicinity, a fine-dining concept announced in January 2026 by the Mercury News, is preparing to debut in the upper tier of downtown alongside Forbes Mill Steakhouse and Tasting House.
- Pergamon Bistro, a Turkish concept from owner Seyyat Zira, is planned for 309 N Santa Cruz Avenue, near Oak & Rye and Pedro's. An opening date has not been announced, but the alcohol license application was on file as of early 2026.
Read the list together and a pattern shows up. Four of the six openings are Mediterranean or Mediterranean-adjacent. Two of them, Dar and the Abik project, are two blocks apart on the same downtown strip. This is not a coincidence anyone planned. It is what happens when a block with high foot traffic and a strong resident base becomes attractive to operators who have already proven themselves one town over.
A festival Saturday, walked
Here is a way to use the block that treats the festival as one stop in a longer day rather than the whole day.
| Time | Where | Why |
|---|---|---|
| 9:00 AM | Town Plaza Farmers' Market | Produce, crepes, artisanal goods, the weekly reset. |
| 10:00 AM | Purple Onion Café, near the Los Gatos Creek Trail entrance on Main | Coffee and pastry before the crowds swell. |
| 11:00 AM | Civic Center Lawn | Enter the festival on the earlier side, before the afternoon line at the pour booths. |
| 1:30 PM | Southern Kitchen | Family-owned, no reservations, weekend brunch that runs into early afternoon. |
| 4:00 PM | Second lap of the festival | The vendor booths thin out, the music picks up. |
| 6:30 PM | Heritage Pub and Chop House or Dar | Sit-down dinner without leaving the two-block radius. |
| 9:00 PM | PintxoPote, 424 N Santa Cruz Avenue | Spanish tapas across from the Downtown Los Gatos sign, for the plates-and-sangria hour. |
The point of the schedule is not the schedule. It is that you can now build a full Saturday inside a five-minute walking radius without repeating a restaurant you were already tired of last year.
Vacant for the last seven years, the second story of the La Cañada Building is now Heritage Pub and Chop House. Petals Creamery opened downstairs this summer. Second Story opened late last year. One building, three new reasons to stop in.
What the Sunday feels like after
Sunday of festival weekend has a natural shape. The Farmers' Market at Town Plaza opens at 9:00 AM. Purple Onion Café sits at the trail entrance for the post-market coffee window. Southern Kitchen handles the brunch hour for the crowd that skipped the Saturday line. The festival reopens on the lawn at 10:00 AM and runs until 6:30 PM. If you did the first day heavy, Sunday is the day to bring out-of-town family who want to say they went without committing to eight hours of it.
One quiet upside of the recent openings is that they have added late-afternoon and dinner options that hold up when you have visiting relatives who want somewhere that feels like Los Gatos rather than somewhere they could get in their own city. Dar's fireplace patio, Heritage's game hall and shuffleboard, and the eventual Abik room at 25 E. Main all sit in that category.
The pattern under the openings
The easy read on downtown right now is that Los Gatos has become a hot dining town. The more accurate read is that the operators taking the leases are people with personal stakes in this specific block. Walker Pearce-Percy graduated from Los Gatos High School in the class of '97. Kristi grew up here too. The Shaqir brothers built their following one town over in Saratoga before crossing the hill. Abik chose 25 E. Main after fifteen years of running kitchens in San Francisco. These are not chain outposts. They are places that were opened by people who already knew what a Saturday in September looks like on this street.
That is the shift worth holding onto as you walk the festival this year. The event is the same. The block underneath it is not.
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