Planning a trip to Willow Glen and wondering what events are worth timing your visit around? Every event on Lincoln Avenue organised by the Willow Glen Business Association, from free evening street events to ticketed wine and beer walks, is listed here with dates, formats, and what to expect before you go.
Downtown Willow Glen runs a full calendar of annual events along Lincoln Avenue. Some are free and open to everyone. Others are ticketed and sell out in advance. Knowing the difference before you plan saves you the disappointment of turning up to find wristbands sold out at the door.
How Downtown Willow Glen Events Are Organised
Every event covered in this guide is organised by the Downtown Willow Glen Business Association, a non-profit representing over 250 businesses along Lincoln Avenue and the surrounding blocks. The association runs both free community events open to all and ticketed walk events where participants pay for a souvenir glass, wristband, and map to tasting sites hosted by participating businesses.
Free events: A Night on the Avenue, Glen Fest, Trick or Treat Along Lincoln Ave, Mrs Roper’s Romp, Founders Day
Ticketed events: Beer Walk, Spring Wine Walk, Holiday Bubbly Walk
All events take place on or along Lincoln Avenue, Downtown Willow Glen, San Jose, CA 95125. Updates and announcements are posted at willowglen.org and on Instagram at @downtownwillowglen.
February: A Night on the Avenue
Format: Free, no ticket required Location: Lincoln Avenue, Downtown Willow Glen
A Night on the Avenue opens the Downtown Willow Glen events calendar each February. The most recent edition ran on Saturday, February 5, 2026 from 4pm to 8pm along Lincoln Avenue, turning the street into a free evening event with special promotions, live entertainment, and extended hours at participating merchants.
At the 2026 edition, live entertainment ran at Copita Tequileriay Comida, where Chef Azari presented a special menu. Sushi Confidential offered 20 percent off food and beverages. BellaJames ran 15 percent off all purchases. Whatnots and Dodads offered no sales tax plus 10 percent off. Aldea Home served refreshments and offered free gift bags with qualifying purchases.
A Night on the Avenue draws both residents and first-time visitors. With free entry and participating merchants across the full length of Lincoln Avenue, it works as a low-commitment introduction to the neighbourhood for anyone planning a weekend in Willow Glen for the first time.Â
April: Spring Wine Walk
Format: Ticketed Location: Lincoln Avenue, Downtown Willow Glen Check-in: Bank of America parking lot, 1245 Lincoln Avenue
The Spring Wine Walk follows the same format as the Beer Walk and Holiday Bubbly Walk: one ticket, one souvenir glass, one map, and a self-guided afternoon tasting at businesses hosted along Lincoln Avenue. The 2026 Spring Wine Walk ran on April 18th from 2pm to 5pm.
Participating wineries range from Bay Area producers to Central Coast California labels. The self-guided format means attendees move at their own pace between tasting sites set up inside and outside participating Downtown Willow Glen businesses.
June: Downtown Willow Glen Beer Walk
Format: Ticketed Date 2026: Saturday, June 20, 2026 Time: 2pm to 5pm Check-in: Bank of America parking lot, 1245 Lincoln Avenue, from 12pm to 3pm
The Beer Walk is a self-guided craft beer tasting event along Lincoln Avenue. Participants receive a souvenir glass, a wristband for all tasting sites, and a printed map to every stop on the route. Tasting sites are hosted inside and outside participating businesses along the avenue.
The 2025 Beer Walk featured breweries including Fox Tale Fermentation Project, Lagunitas Brewing Co., Sierra Nevada Brewing Co., Firestone Walker Brewing Co., Fieldworks Brewing Co., Karl Strauss Brewing Company, and over a dozen others from across the Bay Area.
A few confirmed rules worth knowing before attending: drinks cannot be carried between tasting sites under California ABC regulations. ID is checked at every tasting site without exception. Tasting site bathrooms are not available to Beer Walk attendees. Port-a-lets are provided at the Bank of America parking lot. Designated drivers do not require a ticket.
July and August: Willow Glen Farmers Market Summer Season
Format: Free, no ticket required Location: Willow Glen Elementary, 1425 Lincoln Avenue Hours: Saturdays 9am to 1pm, year-round
The Willow Glen Farmers Market runs every Saturday year-round, but the summer months between June and August are when attendance peaks. The market operates on Sundays during the summer season, moving from its regular Saturday slot.Â
The market carries California-grown seasonal produce, fresh flowers, honey, dairy, fish, meats, artisanal baked goods, and over ten prepared food vendors. Live music runs every week alongside face painters and market basket raffles. For a full picture of what vendors sell and how the market runs each Saturday, the dedicated farmers market page covers hours, EBT acceptance, pet policy, and parking in detail.
September: Glen Fest and Founders Day
Glen Fest
Format: Free, no ticket required Location: Lincoln Avenue, Downtown Willow Glen Time: 11am to 6pm
Glen Fest runs in September and is the largest single-day community event on the Downtown Willow Glen calendar. The event features local and unique food trucks and food vendors, live bands across the full event day, beer, wine, and a kids court with bouncy houses, face painting, and a photo booth.
A Yelp reviewer who attended described the atmosphere: “It’s a lot of fun to spend the Saturday walking in downtown Willow Glen and just enjoying the music and the food and all of the shops. Good atmosphere, dog friendly, music was good, they had one stage with performers in front of a big crowd.”
Glen Fest draws the largest single-day crowd of the year on Lincoln Avenue. Anyone arriving early and wanting to explore the avenue before the crowds build will find the best outdoor dining spots on Lincoln Avenue worth knowing in advance.
Founders Day
Format: Free, no ticket required Location: Lincoln Avenue, Downtown Willow Glen
Founders Day falls in September and celebrates the history and cultural heritage of Willow Glen. A festive parade proceeds down Lincoln Avenue as the centrepiece of the event.
The occasion traces back to a specific piece of local history. Willow Glen operated as its own incorporated city from September 8, 1927, when residents voted to incorporate in order to prevent the Southern Pacific Railroad from routing its trunk line through the community, until September 4, 1936, when residents voted to be annexed into San Jose to connect to the city’s sewer system. Founders Day marks those nine years of independence with an annual parade and community celebration.
Few visitors know Founders Day exists. No mainstream San Jose events guide covers it. Attending gives a visitor something genuinely specific to Willow Glen that no other neighbourhood in San Jose offers. For more on the neighbourhood’s history, parks, local businesses, and hidden gems cover the side of Willow Glen most visitors never find.
October: Trick or Treat Along Lincoln Ave
Format: Free, no ticket required Location: Lincoln Avenue, Downtown Willow Glen
Trick or Treat Along Lincoln Ave is the Halloween event on the Downtown Willow Glen calendar. Participating businesses along Lincoln Avenue open their doors to families for a safe, street-level trick-or-treat experience on Halloween or the nearest Saturday.
The event draws families from across San Jose who want a walkable, community-based alternative to residential street trick-or-treating. Families visiting the neighbourhood for the first time will find the independent shops, bookstores, and local spots along Lincoln Avenue worth exploring before or after the event.
December: Holiday Bubbly Walk
Format: Ticketed, sells out in advance Date 2025: Saturday, December 6, 2025 Time: 2pm to 5pm Check-in: Bank of America parking lot, 1245 Lincoln Avenue, from 12pm to 3pm
The Holiday Bubbly Walk is the most popular ticketed event on the Downtown Willow Glen calendar and consistently sells out faster than the Beer Walk and Wine Walk. Participants stroll along Lincoln Avenue visiting over two dozen businesses for sparkling wine tastings. A souvenir glass, wristband, and printed map are included with the ticket.
At the 2025 edition, participating businesses included Copita Tequileria y Comida, Sushi Confidential, 20Twenty Wine Bar, and Mariette Chocolates. Early bird pricing for the 2025 edition was $60 plus fees through November 30, rising to $65 plus fees afterward.
Lincoln Avenue is decorated for Christmas during the Bubbly Walk, which coincides with the Willow Glen neighbourhood’s Christmas decoration tradition. Residents across multiple residential streets coordinate themed holiday displays each December, making the walk along the avenue in early December one of the more festive evenings available anywhere in the South Bay.Festive attire is encouraged by the organisers to add to the atmosphere as attendees move between tasting sites.
The Events Calendar at a Glance
Month | Event | Free or Ticketed |
February | A Night on the Avenue | Free |
April | Spring Wine Walk | Ticketed |
June | Beer Walk | Ticketed |
Jul to Aug | Farmers Market summer season | Free |
September | Glen Fest | Free |
September | Founders Day Parade | Free |
October | Trick or Treat Along Lincoln Ave | Free |
December | Holiday Bubbly Walk | Ticketed |
All events are along Lincoln Avenue, Downtown Willow Glen, San Jose, CA 95125. Dates for each year are confirmed on theDowntown Willow Glen Business Association website and on Instagram at @downtownwillowglen.
Plan Your Visit to Downtown Willow Glen
Every event on Lincoln Avenue is a reason to visit the neighbourhood, but the street rewards coming when no event is on as much as when one is. Browse local businesses, upcoming events, and neighbourhood highlights at Downtown Willow Glen.
