Just like Ebenezer Scrooge in Charles Dickens’ “A Christmas Carol,” Healdsburg has witnessed Christmases of the past, present and future. The centerpiece of Christmas Present is the majestic, bejeweled and lighted tree erected in the Plaza by the city and the tourism improvement district. It is a stunning addition to the town’s bustling crosswalks. Healdsburg’s Christmas Future will be the one celebrated without masks and COVID-19 pandemic restrictions. And, Healdsburg’s Christmases Past hold many tales of earlier spirits, cherished memories and a few episodes almost lost to history.
This year’s Plaza tree is a true holiday highlight, but does anyone remember Healdsburg’s holiday time flying elves? Before wine tasting rooms, restaurants and inns ringed the Plaza, the local holiday decorating and event budget was fairly meager. A generation ago, the fledgling downtown business association tried to compete with well-funded destinations like Coddingtown, Montgomery Village and the new Santa Rosa Mall. Out of this David versus Goliath tale was born the idea for Healdsburg to be the selected location for two of Santa’s elves to parachute onto the town’s green. Big plans were made and promotions were prepared for radio, TV and newspapers. Healdsburg — not yet discovered as a Wine Country capital — would earn a star on the Bay Area map. Except the elves never landed.
This year’s holiday tree is by far a major upgrade over all previous evergreen displays. The tree is a 50-foot-tall white fir from Grants Pass, Oregon. It is decorated with 3,000 LED lights and 502 ornaments. Including transportation costs, crane installation and decoration labor the tree cost $13,425, according to Mark Themig, community services director for the City of Healdsburg. The expenses were covered by a grant from the Healdsburg Tourism Improvement District. Themig said most of the costs are one-time and next year’s costs will depend on the size of the tree.
The city spent another $24,000 on street pole, archway, gazebo and other decorative holiday lighting.
“We tried lots of things through those years,” remembered Lynn Woznicki, who was the executive director and president of the Healdsburg Chamber of Commerce for at least two decades  (1980s and 1990s) of Healdsburg Christmases Past. “We never had enough money, but we sure did many things. We just thought if we could create something the locals would like, then maybe others would come here to shop and enjoy the holidays, too.”
In those days, Healdsburg may have been home to the region’s smallest Santa parade. Carla Howell owned Cubbyhouse, a children’s clothing shop on the Plaza. One Christmas in the mid-1980s she asked the Healdsburg Fire Department to line up their antique engine in the Bank of America parking lot at Center and Piper streets. She found a volunteer Santa and invited anyone who wanted to to march behind the red engine with Santa aboard. The “parade” ended at the Plaza and Santa would then greet children in the Plaza’s gazebo. Free photos were taken with film that was processed a few days later at the local Verbil Camera Shop. In those years, Santa also had a throne in the local J.C. Penney store, the current location of the shuttered Raven Film Center.
“We were struggling to get people to stay and shop in Healdsburg,” remembered Howell, who later was elected mayor and also served as executive director for the chamber. “We did window painting contests and had caroling in the Plaza. We tried staying open on Sundays and we tried decorating all the different trees in the Plaza, but none of them worked very well.”
Nursery owner Jerry Strong donated an evergreen that was planted in the Plaza with hopes it would grow into the town’s holiday tree. Before it reached much height, a windstorm knocked it over and it had to be removed.
“It was our Charlie Brown Christmas tree,” Howell said.
When Hotel Healdsburg was built in 2001 and other inns became popular, the city and chamber benefited from transient occupancy taxes (TOT) and the holiday event budget grew.
“We got matching funds from the redevelopment agency and from the Healdsburg Auto Dealers group,” said Woznicki. “Someone said ‘Let’s have a party’ and that’s how the very popular downtown holiday parties started.”
The Healdsburg Holiday Party was held on the Friday after Thanksgiving for over a decade. It preceded the Sonoma County Hospice candle tree lighting ceremony the same weekend.
Each year the Santa parade grew a little longer and Santa photos became digital but many of the young children’s wishes for toys and special secrets didn’t change all that much. When the original volunteer Santa named Ben died, Woznicki asked her husband, then-Healdsburg Tribune editor Ray Holley, to fill in. Holley filled the role for the next decade-plus.
Holley remembers the flying elves caper in the late 1980s. Radio ad man Jim Proctor had been hired by the downtown association to produce holiday promos and events and he concocted the flying elves promo.
“Some people at the time thought it was a ‘flying Elvis,’” Holley said. Lots of people tried to talk Proctor out of the stunt be was secretly planning to go ahead with his plan.
The stage was all set. The land where Hotel Healdsburg now sits was a vacant plot of grass and Proctor planned to have a helicopter swoop down and have two men in elves outfits parasail to the ground. Marie Butler, who was working at the chamber at the time, and a few others remember how rain and inclement weather finally convinced Proctor to call off the elf drop.

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