Glen Fest Returns to Willow Glen for a Day of Music, Food, and Family Fun

The third annual Glen Fest will turn the Bank of America lot on Lincoln Avenue into Willow Glen’s biggest community celebration of the year on September 26. From 11 in the morning until 6 in the evening, local food vendors, beer and wine stands, live bands, and a full Kids Court will draw neighbors together for a full day of outdoor enjoyment.

Two bands will keep the soundtrack going from early afternoon onward. The Wanderers will deliver classic rock and pop hits spanning the 1960s through today between noon and 2:30. Livewire will follow with high-energy dance covers from the 1970s and 1980s plus current favorites, taking over from 3 until 5:30 and inviting everyone to move.

A dedicated Kids Court will offer bouncy houses, face painting, appearances by local sports teams, and additional activities designed for younger visitors. The mix of live music, food, and play creates an easy setting where families can spend hours wandering the lot and nearby tree-lined streets.

Organized by the Willow Glen Business Association, the free event supports independent merchants while giving the neighborhood a signature gathering point. It transforms a central parking area into a vibrant space for eating, dancing, and connecting with people who live and work nearby.

Mrs. Roper Romp Brings Playful Energy to Downtown Willow Glen Once Again

Friends and neighbors seeking a lighthearted summer afternoon in Willow Glen will have the perfect reason to dust off the caftans and wigs this coming weekend. The third annual Mrs. Roper Romp turns the neighborhood into a stage for colorful fun inspired by the Three's Company television character known for her bold fashion and larger-than-life personality.

The gathering takes place on Saturday, July 11 from 1 to 5 PM throughout Downtown Willow Glen. Participants need no tickets or advance sign-ups. They simply choose an outfit that captures the spirit, then spend the hours shopping at local boutiques, enjoying meals at neighborhood restaurants, and strolling the sidewalks in full flamboyant style.

Willow Glen has always carried a village atmosphere with its blend of specialty stores, casual dining spots, and pedestrian-friendly blocks. This is a pretty unique event that I have never seen take place in another part of Silicon Valley. I certainly plan to sit outside at one of Willow Glen's many great restaurants and enjoy the show--watching both those participating and the confused looks from people that stumbled upon the event and have no clue what's going on.

A Night on the Avenue: Evening Delights in Downtown Willow Glen

San Jose's Willow Glen neighborhood hosts A Night on the Avenue on Saturday, February 5, 2026, from 4:00 PM to 8:00 PM along Lincoln Avenue. This free event invites residents and visitors to explore the tree-lined streets filled with sidewalk cafes, boutiques, and easy free parking. Organized by the Willow Glen Business Association, the gathering turns the area into a lively spot for an evening out with friends or family.

Participating merchants offer a range of treats and promotions to enhance the stroll. Live entertainment fills the air at Copita Tequileria y Comida, where Chef Azari presents a special menu. Nearby, Sushi Confidential provides 20 percent off food and beverages, while Aldea Home San Jose serves refreshments. Shoppers find deals like 15 percent off entire purchases at BellaJames, no sales tax plus 10 percent off at Whatnots and Dodads, and free gift bags with qualifying buys at Aldea Home.

Additional highlights include a free brain hack demo and parent tip card pack at Brain Hacks Occupational Therapy, along with 20 percent off party rentals. The event showcases Willow Glen's small-town charm within San Jose, blending diverse dining, unique shopping, and community services in one accessible location.

For full details, visit https://www.willowglen.org/a-night-on-the-avenue.