Willow Glen welcomes back its cherished holiday trolley rides this December, offering a delightful way to experience the neighborhood's festive charm. From December 7 through December 18, the Willow Glen Business Association hosts these evening journeys along tree-lined streets adorned with lights. Riders glide past sidewalk cafes, boutiques, and cozy shops that give the area its small-town appeal within San Jose.
Each ride lasts 30 minutes and departs from the Bank of America lot at 1245 Lincoln Avenue, with departures at 5:15pm, 6pm, 6:45pm, 7:30pm, 8:15pm, and 9pm. The open-air trolley seats up to 32 passengers, providing views of the holiday decorations. Arrive early for check-in to secure a spot on this popular attraction.
Tickets are on sale now, with adults at $40 plus fees and children aged 2 to 12 at $20 plus fees. Kids under 2 ride free on a lap. Dress warmly and bring a blanket, as the trolley exposes riders to the elements. No food or dogs allowed, though drinks with secure lids work fine. Rides proceed in rain, possibly switching to a luxury bus with advance notice.
Private trolley reservations are open for select nights, ideal for groups celebrating the season. Contact the association at info@willowglen.org for details and pricing.
For more information or to purchase tickets, visit https://www.willowglen.org/trolley-rides
San Jose thrives on community gatherings that bring joy to residents and visitors alike. The annual Trick-or-Treat the Row Halloween Family Festival at Santana Row captures this energy perfectly. Held on October 28th from 10 AM to noon, the event turns the stylish shopping and dining district into a playground of seasonal delights for families.
Attendees can dive into a variety of activities designed for all ages. Live music sets a festive tone while pumpkin decorating stations spark creativity. Trick-or-treating along The Row offers sweet rewards, and stilt-walkers add a touch of whimsy. Balloons float through the air, rounding out the morning with even more surprises.
This free celebration encourages everyone to arrive in costumes and carry treat bags to make the most of the experience. No registration is needed, so families can simply show up and join the fun.
Dog Man: The Musical arrives at the San Jose Civic in Downtown San Jose on January 24 and 25, 2026. This production, based on Dav Pilkey's beloved book series, follows the heroic antics of a half-dog, half-policeman character who battles villains while staying true to his playful nature. Tickets go on sale October 24 at 10 a.m., with performances scheduled for Saturday at 3 p.m. and Sunday at noon, offering convenient times for weekend outings.
The story centers on Dog Man's efforts to protect the city from threats like Flippy the cyborg fish and his Beasty Buildings army, alongside Petey the evil cat and his clone. Young creators George and Harold weave the tale, racing to complete their show before lunch. Produced by TheaterWorksUSA, the musical combines humor, music, and heartfelt moments that appeal to kids and adults alike, drawing from Pilkey's other hits like Captain Underpants.
Behind the scenes, the show features book and lyrics by Kevin Del Aguila, music by Brad Alexander, and direction and choreography by Jen Wineman. The creative team includes scenic design by Timothy R. Mackabee, costumes by Heidi Leigh Hanson, lighting by David Lander, sound by Emma Wilk, and orchestrations by Lloyd Kikoler. Originally premiering off-Broadway in 2019 and returning in 2023, the production has earned acclaim for keeping audiences engaged through its lively 90-minute runtime.
For tickets, head over here.
San Jose families have a perfect opportunity to celebrate the spooky season sustainably with Green Halloween at Happy Hollow Park & Zoo on October 25 from 11 a.m. to 2 p.m. This annual event turns the zoo into a hub of Halloween excitement, where visitors can watch animals engage with themed enrichments like pumpkins filled with treats. Happy Hollow offers a welcoming space for all ages to enjoy the festivities while supporting local wildlife conservation efforts.
The day features a variety of activities designed for young explorers, including critter shows, hands-on crafts with a creepy twist, interactive games, and close-up animal encounters. Decomposing decor adds to the eerie yet educational vibe, teaching attendees about natural cycles in an engaging way. Families can participate fully, with everything included in general admission, making it an easy outing for parents looking to create memorable experiences without extra hassle.
What sets Green Halloween apart is its focus on environmental responsibility, aligning with Happy Hollow's status as a certified green facility. The event encourages reusable costumes and highlights ways to make holidays more planet-friendly, inspiring attendees to adopt similar practices at home. This approach not only entertains but also fosters a sense of community stewardship, showing how San Jose leads in blending fun with sustainability.
Tickets range from $15 to $18, with a $3 discount for those arriving in costume, rewarding creativity and participation. Members enjoy free entry, adding value for regular visitors. As San Jose continues to prioritize green initiatives, events like this strengthen the city's appeal as a family-oriented destination that values both entertainment and the environment.
Playful People Productions presents Disney's Newsies from November 8 to 16, 2025, at the Historic Hoover Theater. This Tony Award-winning musical, based on the 1899 Newsboys Strike, features two casts of teen and adult performers bringing the story to life. Set in early 20th-century New York City, the production follows charismatic newsboy Jack Kelly as he leads a group of young paper sellers in a stand against powerful publishers raising prices. The tale highlights themes of unity and justice, with reporter Katherine Plumber joining the cause to prove her worth in a male-dominated field.
The show includes memorable songs like Watch What Happens, Carrying the Banner, Seize the Day, King of New York, and Santa Fe, composed by Alan Menken with lyrics by Jack Feldman and a book by Harvey Fierstein. Directed by Katie D'Arcey and Emily Pennington, with vocal direction from Jacqueline Whitaker and choreography by Emily Pennington, the performances promise high energy and engaging dances. Two casts, named World and Sun, alternate showtimes, offering multiple chances to catch the action. Tickets range from $22 for youth under 12 to $30 for adults, making it an affordable outing for families and friends.
As part of its 15th anniversary season, Playful People Productions continues to foster inclusive theater experiences in San Jose. Founded in 2010 and operating as a nonprofit since 2017, the organization emphasizes positive discipline and creative growth for all ages. It provides classes, camps, and multi-generational shows where family members perform together, creating bonds that extend beyond the stage. Supported by grants from the City of San Jose and SVCreates in partnership with Santa Clara County, this production exemplifies the community's commitment to arts education.
The Historic Hoover Theater is located at 1635 Park Avenue and you can find more info and tickets over here.
San Jose welcomes a vibrant celebration of music and creativity this weekend with Kids Day in the Park at Plaza de César Chávez. Families can look forward to live performances from Lisa Loeb and The Hollow Trees, who join forces for a special set drawn from their new album, That’s What It’s All About. This collaboration mixes Loeb's storytelling style with the folk energy of The Hollow Trees, offering tunes that honor family traditions and classic songs. The event promises an engaging afternoon where attendees sing and dance together in the heart of the city.
Adding to the lineup, the Alphabet Rockers deliver their signature mix of melodies and meaningful lyrics. Founded in Oakland in 2007 by Kaitlin McGaw and Tommy Soulati Shepherd, this group has earned a Grammy for Best Children's Music Album along with other nominations. Their music spans animated series and global audiences, bringing positive vibes that resonate with kids and parents alike. Seeing them perform in San Jose highlights the Bay Area's rich talent pool and creates lasting memories for local families.
Beyond the stage, the festival includes plenty of activities to keep everyone entertained. Face painting stations spark imagination, while bouncy houses provide energetic playtime. Exhibits showcase interactive displays, and food trucks serve up tasty options for all ages. Held at 1 Paseo de San Antonio, this free gathering on September 20 turns Plaza de César Chávez into a family-friendly entertainment hub. For mor info and tickets, click here.
San Jose invites everyone to join the 10th anniversary of Viva CalleSJ on September 7, 2025, from 10am to 3pm, transforming nearly 10 miles of streets into car-free spaces for walking, biking, skating, and exploring. Named Las Calles, this edition combines favorite routes from the past decade, weaving through eclectic neighborhoods to foster community connections and active lifestyles. Participants of all ages and abilities can start anywhere along the path, moving at their own pace to discover local gems and enjoy the city's vibrant energy.
Activity hubs at the Municipal Rose Garden, Watson Park, and Willow Glen at Lincoln and Minnesota avenues serve as focal points with food trucks, live entertainment, and free minor bike repairs. Expect surprises like BMX shows, cultural displays, and unique sights such as vintage penny farthings or creative bike setups that add to the fun. The event encourages safe participation with rules like wearing helmets for those under 18, staying aware of surroundings, and using public transit like VTA to reach the route easily.
This milestone highlights San Jose's commitment to health, local businesses, and inclusive recreation, drawing over 100,000 people in past years to build lasting memories. Viva CalleSJ opens streets to wheelchairs, scooters, and other mobility aids, ensuring broad access while promoting sustainability.
San Jose families have a timeless favorite returning with a modern twist as Happy Hollow Park & Zoo reopens the Danny the Dragon ride after a thorough nine-month renovation. This beloved attraction, originally built in 1958, now features an updated journey through five themed lands that mirror the park's diverse habitats. Riders will glide along the half-mile track, exploring areas like a farm, jungle, and land of enchantment, all designed to create an immersive storyline that sparks wonder for visitors of all ages.
Over $600,000 was raised by donors to the Happy Hollow Foundation (I'm proud to be one of them). City staff dedicated nearly a year of skilled work to bring the vision to life, replacing the original fluorescent tunnel and storybook theme with something more engaging for today's guests. This marks the ride's first scenery refresh in 64 years, blending nostalgia with contemporary appeal to draw in new generations.
Since Happy Hollow opened in 1961, attractions like Danny the Dragon have created lasting memories, with parents and grandparents sharing stories of their own childhood rides. Now, this revitalized ride stands ready to welcome guests. The official ribbon cutting was yesterday and Danny the Dragon is now ready for visitors to enjoy immediately.
San Jose’s beloved Happy Hollow Park & Zoo is breathing new life into one of its most iconic attractions—Danny the Dragon! For over six decades, this whimsical train ride has been a cornerstone of family fun in our city, delighting generations with its quirky charm and playful journey through the park. Now, thanks to a renovation project, Danny is set to soar to new heights, and we can’t wait to see what’s in store.
The Happy Hollow Foundation recently launched a $500,000 capital campaign to “reimagine” Danny the Dragon, ensuring this treasured mascot remains a vibrant part of San Jose’s story for years to come. This renovation goes beyond a simple spruce-up—it’s a full transformation. The updated Danny will evolve from a classic train ride into an immersive experience, guiding visitors through themed “lands” that reflect the diverse habitats found at Happy Hollow.
What makes this project extra special is its focus on community. The goal is to fund the entire renovation through local support, with donors earning a unique perk: their names will be featured on “dragon scales” along the ride’s queue fence (I ordered one myself). It’s a chance for San Joseans to leave their mark on a piece of the city’s history.
Below are some of the concepts for the reimagining of the ride, which is expected to be complete later this year. If you are interested in learning more or contributing to the project, head over here!
