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Art and wine festivals are a Peninsula summer habit. A town closes its main street for a weekend, white tents go up on both sides, bands play at each end and a beer and wine booth raises money for a service club or chamber of commerce. The formula barely changes from town to town. What changes is the setting, the size and how easy it is to get there from Palo Alto.
This calendar covers the recurring festivals on the Peninsula and in the South Bay, listed in the order they fall. Each entry gives the most recent date we could confirm on an organizer page or in local press, the venue, the usual timing and the best route from Palo Alto. When we checked on November 2, 2026, none had posted 2027 dates, so treat the usual weekend as a guide until they do.
The season at a glance
| Festival | Latest confirmed date | Usual timing | From Palo Alto |
|---|---|---|---|
| Sunnyvale Art and Wine | June 6 and 7, 2026 | First weekend of June | Caltrain to Sunnyvale |
| Los Altos Arts and Wine | July 11 and 12, 2026 | A July weekend | Car or bike, about 5 miles |
| Palo Alto Festival of the Arts | August 22 and 23, 2026 | Late August | Walk from Palo Alto station |
| Millbrae Art and Wine | September 5 and 6, 2026 | Labor Day weekend | Caltrain to Millbrae |
| Mountain View Art and Wine | September 12 and 13, 2026 | Weekend after Labor Day | Caltrain to Mountain View |
| Santa Clara Art and Wine | September 19 and 20, 2026 | Mid-September | Car, about 13 miles |
| Los Gatos Art and Wine | September 26 and 27, 2026 | Late September | Car, about 18 miles |
| San Carlos Art and Wine Faire | October 10 and 11, 2026 | Second weekend of October | Caltrain to San Carlos |
June and July: Sunnyvale and Los Altos
Sunnyvale Art and Wine Festival
The season opens in downtown Sunnyvale. The 2026 festival was the 50th and ran Saturday, June 6, from 11 a.m. to 7 p.m. and Sunday, June 7, from 10 a.m. to 5 p.m., according to the Mountain View Voice. The organizers described more than 200 artists, live music, food and drink and a kids' zone in a redesigned layout around Murphy Avenue. Admission was free. Watch sunnyvaleartandwine.com for 2027. Sunnyvale station sits at the foot of Murphy Avenue, so the train drops you at the first booths. Our Sunnyvale guide covers the town.
Los Altos Arts and Wine Festival
The Los Altos Village Association runs this one on Main and State streets. The 47th edition was Saturday and Sunday, July 11 and 12, 2026, from 10 a.m. to 6 p.m., with two music stages, a Kidzone and drinks from local producers paid by card or tap only. It is the most compact festival on the list and the easiest by bike from south Palo Alto. There is no train station in downtown Los Altos.
August: Palo Alto Festival of the Arts
Palo Alto's own festival is the one with the strongest fine art focus. The Palo Alto Chamber of Commerce hosts it on University Avenue. The 2026 festival, the 43rd, ran August 22 and 23 from 10 a.m. to 6 p.m. with about 250 artist booths and the Italian Street Painting Expo on Tasso Street. The Kiwanis Club pours beer and wine. Entry is free. The 2027 dates were not posted in early November 2026. Our Festival of the Arts guide has the details and parking tips.
September: four festivals in four weekends
Millbrae Art and Wine Festival
Millbrae's festival fills Broadway between Victoria and Meadow Glen avenues over Labor Day weekend. The 55th edition ran Saturday and Sunday, September 5 and 6, 2026, from 10 a.m. to 5 p.m., with more than 170 artists, a beer tent, wine tasting and a kids' area, according to the Mountain View Voice. Admission was free. The Millbrae Chamber of Commerce organizes it. Millbrae station is a short walk away. The express trip from Palo Alto takes about 21 minutes. Our Millbrae guide has food ideas.
Mountain View Art and Wine Festival
The biggest of the group by artist count. The 54th festival ran September 12 and 13, 2026, on Castro Street, with more than 400 artists, two stages and a ticketed wine lounge ($65 at the door in 2026). Mountain View station sits at the north end of the festival. See our Mountain View Art and Wine guide.
Santa Clara Art and Wine Festival
The City of Santa Clara runs its festival in Central Park, 909 Kiely Boulevard. The 44th edition was Saturday, September 19, from 10 a.m. to 6 p.m. and Sunday, September 20, from 10 a.m. to 5 p.m. The Mountain View Voice counted more than 170 artists and craft vendors. The city's festival page listed food from $4 to $25 and beer and wine tokens at $10 each. Entry was free, but parking at Fatjo Field was $15 and at St. Justin Catholic Church $20. A grassy park setting makes it the most family-friendly of the September four. Drive down El Camino Real or Central Expressway, about 13 miles.
Los Gatos Art and Wine Festival
Los Gatos closes out September on the Civic Center lawn at 110 East Main Street. The festival ran September 26 and 27, 2026, from 10 a.m. to 6:30 p.m., with free admission, per the Mountain View Voice. Earlier editions, including 2025, went by the name Fiesta de Artes, which is why the website is still losgatosfiesta.com. The town has no Caltrain stop, so drive via Highway 85 and park in the downtown lots early. Our Los Gatos guide covers the town.
October: San Carlos and the coast
San Carlos Art and Wine Faire
The last of the classic street fairs falls on the second weekend of October. The 2026 faire ran Saturday and Sunday, October 10 and 11, from 10 a.m. to 6 p.m. at San Carlos Avenue and Laurel Street, with more than 200 artists, three stages and a family fun zone. Admission was free. The City of San Carlos hosts it. Pacific Fine Arts handles artist booking. San Carlos station is a block from Laurel Street. Our San Carlos guide lists restaurants on Laurel.
Two October cousins
Two more October events follow the same format with a twist. The Half Moon Bay Art and Pumpkin Festival ran October 17 and 18, 2026, with about 275 artists and makers along Main Street. Campbell Oktoberfest ran the same weekend downtown, with more than 100 arts and crafts booths and beer instead of wine. Both are covered in our food festivals guide.
Good to know
- Bring ID. Every beer and wine booth checks. Many hand you a wristband first.
- Booth prices run from cards and small prints to large originals. Ask artists about shipping big pieces.
- September afternoons are often the warmest of the year here. Bring water and a hat.
- Dogs are discouraged at most of these festivals because of crowds and hot pavement.
How to choose and plan
- Pick by setting. Palo Alto and Los Altos feel like neighborhood events. Mountain View is the largest. Santa Clara has shade and lawns.
- Use the train. Sunnyvale, Mountain View, San Carlos and Millbrae are all walkable from Caltrain, which saves a hunt for parking. Our Caltrain guide covers weekend service and fares.
- Go early. The first two hours have the best choice of art and the coolest air.
- Lap first, buy second. Walk the whole festival once, note booths, then circle back.
- Check the week before. Organizers post maps, music lineups and any street closures shortly before each festival.
Making a weekend of it
If you are visiting from out of town, the Palo Alto and Mountain View weekends are the ones that can tighten local hotels, especially when they line up with Stanford move-in or a home football game. You can compare hotels for a festival weekend and pick a refundable rate while you wait for 2027 dates. Our September guide covers the rest of the busiest festival month.
Frequently asked questions
What art and wine festivals are near Palo Alto?
The closest are the Palo Alto Festival of the Arts in late August, the Los Altos Arts and Wine Festival in July and the Mountain View Art and Wine Festival in September. Sunnyvale, Millbrae, Santa Clara, Los Gatos and San Carlos hold their own between June and October.
Are art and wine festivals free?
Yes. Every festival on this list was free to enter in 2026. You pay for food, drinks and anything you buy from the artists. Some festivals sell drink tokens or a separate wine lounge ticket, such as Mountain View's $65 tasting lounge in 2026.
When is the Sunnyvale Art and Wine Festival?
It is held on the first weekend of June on Murphy Avenue and the surrounding blocks of downtown Sunnyvale. The 50th festival ran June 6 and 7, 2026, with more than 200 artists. The 2027 date had not been posted as of November 2, 2026.
Which art and wine festival is easiest to reach by Caltrain?
Mountain View, Sunnyvale, San Carlos and Millbrae all sit within a short walk of a Caltrain station. Palo Alto's own festival is a short walk from Palo Alto station. Los Altos, Santa Clara's Central Park and Los Gatos need a car, bike or bus.
When do 2027 art and wine festival dates come out?
Most organizers post the next year's dates in winter or spring. None of the festivals on this list had posted 2027 dates as of November 2, 2026. Most hold the same weekend slot each year, so the usual timing in our table is a good guide until dates appear.