Festival of Trees: Celebrates Five Years of Holiday Magic and Community Giving

By Cesar A Reyes

For Bobby Gordon, founder of Festival of Trees San Diego, Christmas isn’t just one day; it’s a year-long passion project filled with planning, creativity, and community. “It’s basically Christmas for me every day in my life because of all the planning that goes into making the event happen,” he says with a laugh. When he’s not busy orchestrating one of San Diego’s most beloved holiday fundraisers, Bobby works full-time in marketing and communications, teaches at UCSD Extension, and serves as a public speaker. But it’s this event, the Festival of Trees, that has captured his heart and the hearts of the community.

This year marks the festival’s fifth anniversary, a milestone that fills Bobby with gratitude and awe. “This event has grown to become a Hillcrest holiday kick-off tradition,” he shares. “It’s evolved into something far beyond what I ever could have imagined, dreamt of, or envisioned.” What began as a small holiday fundraiser has blossomed into a citywide celebration that brings together over a hundred businesses, organizations, and individuals each year to create something truly special.

A Dream Grown Beyond Expectation

When Bobby first moved to San Diego, he immediately saw potential in the vibrant energy of Hillcrest. InsideOUT, a favorite local spot, became the festival’s first home. “I immediately envisioned the unique layout as the perfect venue for a holiday fundraiser,” he recalls. The idea was simple yet heartfelt: local organizations would donate and decorate trees, which would then be auctioned to raise funds for local charities.

The first Festival of Trees was pulled together by a small group of about six volunteers. Today, that modest team has grown into a year-round volunteer force led by Bobby Vargas, who helps ensure the event runs seamlessly. “It’s incredible to think about how far we’ve come,” Bobby says.

After a few successful years, the festival outgrew its original home and moved to Rich’s San Diego, where it found the space and atmosphere needed to elevate the experience. “Ryan Bedrosian and his team at Rich’s have been so generous and supportive,” Bobby notes. “The move gave us room for VIP seating and a more immersive experience where guests can enjoy the trees up-close.”

Adding to the excitement, the event now features the dazzling Shannel—yes, that Shannel from RuPaul’s Drag Race—as host and auctioneer for the second year in a row. “Having Shannel involved really brings the energy,” Bobby says. “It’s something we never could have predicted when we first started.”

Growing Impact, Year After Year

What began as a cheerful holiday get-together has evolved into a powerful vehicle for community support. Since its inception, the Festival of Trees has raised over $179,000 for local organizations. The first three years benefited Being Alive HIV/AIDS Services, bringing in $27,500 in year one, $40,000 in year two, and $46,000 in year three. Last year’s event hit a record $66,000 for the North County LGBTQ Resource Center.

“I never envisioned this little holiday party would raise so much or make such a meaningful impact,” Bobby admits. “We’ve always been transparent about where the money goes: once we pay for the event and required insurance, 100% of proceeds go directly to the beneficiaries.”

This volunteer-run, low-overhead event ensures that funds go where they’re needed most: supporting local HIV/AIDS resources and LGBTQ+ youth suicide prevention. “Given the current political climate—the cuts to HIV/AIDS funding, the loss of the federal LGBTQ+ suicide hotline, and the increase in polarized attacks—it’s more important than ever that we come together and support each other,” Bobby emphasizes.

What to Expect at the 2025 Festival

The fifth anniversary celebration promises to be the most spectacular yet. Guests can expect over-the-top, elaborately decorated artificial trees donated by local businesses, each one a unique work of art. These trees are auctioned live during the event—and the fun doesn’t end there. Winners don’t have to worry about hauling their new holiday centerpiece home; members of the San Diego Armada Rugby Football Club deliver each tree the very next day, just in time for Thanksgiving.

Alongside the live auction, guests can browse a robust silent auction, participate in the popular Travel Raffle offering cash prizes and airline tickets, and enjoy the official tree lighting ceremony. Naughty Santa and his crew will be on hand for photos, and the night will wrap up with an after-party hosted by Rich’s to keep the festivities going.

This year’s VIP experience is especially exclusive, featuring early access from 4–5 PM, special seating, and a custom five-year commemorative ornament. “We’re almost sold out of VIP tickets,” Bobby says, “and we’re expecting another full house for the main event.”

The main event runs from 5–8 PM on Sunday, November 23, 2025, at Rich’s San Diego. Tickets and volunteer opportunities are available now at festivaloftreessd.org.

The Heart of It All

At its core, the Festival of Trees is more than just a holiday party—it’s a reflection of what can happen when a community comes together with love, creativity, and generosity. “Giving back has always been at the heart of this event,” Bobby says. “The holidays are a natural time for reflection and connection, and through Festival of Trees, we get to celebrate that spirit while making a real difference.”

Five years in, the Festival of Trees continues to grow. But the mission remains the same: to spread joy, build community, and light up San Diego with holiday magic for a good cause.