Montclair Village Holiday Stroll returning next week with familiar fanfare

The jubilant return Dec. 9 of the annual Montclair Village Holiday Stroll will have streets of the cozy enclave teaming with the Dancing Christmas Trees, an ice queen on stilts, costumed student dancers from the Oakland Ballet’s cast of “The Nutcracker” and Santa in a winter wonderland prepared for family photo-taking.

The cherubic voices of the Pacific Boychoir Academy will mingle with the sounds of friendly greetings called out by people excited to be shopping, dining and celebrating the return of the community event after nearly 21 months of the COVID-19 pandemic. This year’s 18th stroll from 5:30 to 8 p.m. will include a toy donation drive hosted by the Oakland Fire Department, in-person interaction with Oakland District 4 City Councilmember Sheng Thao and Village plaza updates and other information from the event’s presenter, the Montclair Village Association (MVA,

The Dancing Christmas Trees from a previous Montclair Village Holiday Stroll, Oakland’s Daniela Hamann-Nazaroff, from left, and Alameda’s Jessica Martin and Carol Fitzgerald, entertain visitors to the Oakland hills’ Montclair Village during the annual holiday gathering. (Doug Duran — staff archives) 

Most importantly, dozens of local retail, service and dining establishments tucked into the walkable Village’s intimate downtown footprint will offer discounts and special activities. Winter Williams, an MVA board member and past president, is well versed in the trials and tribulations local small businesses have endured during and even before the pandemic lockdown. As a former manager at the Montclair branch of Bank of the West, she joined the association in 2006.

“The market then was coming off a difficult time. I engaged so I could do my part with more than just managing the bank branch,” Williams said.

Her two children attended Thornhill Elementary School at the time and because the nonprofit MVA supports many programs for kids, Williams felt extra motivation to volunteer. Off the board for a time, she rejoined last year because of the pandemic.

The Pacific Boychoir Academy’s voices will mingle with the sounds of friendly greetings called out by people excited to be shopping, dining and celebrating the Dec. 9 return of the Montclair Village Holiday Stroll after nearly 21 months of the COVID-19 pandemic. (photo courtesy of Melissa Rivers — BANG archives) 

“I was off for 10 years but with the shutdown’s economic impact on small businesses and my experience with small business lending — plus I’m now an entrepreneur — I realized this is one of the areas where I know how to advise and make a difference,” she said.

Williams is owner and founder of Family Dog Walkers, a licensed canine care service operated out of her home near Lake Temescal, a few miles from Montclair Village.

“I grew up all over the Bay Area and probably moved 18 times in my first 18 years. I moved here in 2002, and when I found Oakland and felt it was home, I planted roots,” said Williams.

Those roots have grown deeper during the years working and living in the Village that she describes as “community-centered, commercial, essential and welcoming.”

During the early months of the pandemic lockdown, she closed her dog walking business that includes boarding, daycare, playdates, group walks and grooming services.

“I closed because my interpretation of the county guidance was that if I didn’t have essential workers as clients, we needed to close. It was ambiguous for my industry. But I’m a banker with a compliance background and wanted to do my part as a citizen.”

This year’s 18th Montclair Village Holiday Stroll will include in-person interaction with Oakland District 4 City Councilmember Sheng Thao, above, handing out Thanksgiving meals and COVID-19 safety kits previously in Oakland; a toy donation drive hosted by the Oakland Fire Department; and Village plaza updates and other information from the event’s presenter, the Montclair Village Association. (Ray Chavez — staff archives) 

Williams gradually reopened for business, doing all the work herself until May 2021. Finally able to put four people back on the payroll part-time, she said, “It’s huge to go from vibrant business to nothing to gradually building a team again.”

For other local business owners and the overall retail and restaurant scene, change in Montclair Village has meant McCalou’s moving down the street, outdoor dining and parklets opening up, assorted remodels and merchants scrambling to offer e-commerce and online delivery and takeout services. Williams said throwing their doors completely open to actual customers will be especially thrilling after almost a 21-month hiatus.

“The stroll is for all ages, and any type of family fits in. Not all businesses are open, but of those that are, they’re decorated. It’s fun.” And those Dancing Christmas Trees? Of those Williams said, “You rush from work, and then you see them dancing all over the Village, and it melts whatever harsh shell you’ve built up.”

There will not be a trolley as in years past, and the event is stretched over several hours to reduce the chance of crowds forming and people congregating too closely when visiting businesses indoors. Pictures taken with Santa by Leah Marie Studio inside the F&M Bank location on Antioch Street will be organized to maintain safety; visiting with Councilmember Thao and community resource officers from the Oakland Police Department will take place outdoors in Village plaza on Antioch Court.

Enthusiastic participation from store owners and community members indicate Montclair’s “beloved gatherings” are returning, Williams said, and even modified versions are “better than the last year-and-a-half of canceled events.”

Asked what actions the MVA recommends beyond supporting local businesses and restaurants by shopping for holiday gifts and services and dining at Village restaurants during the stroll, Williams said, “What’s important is to stay connected. We’re coming out of COVID, and we have an opportunity to remember what we’ve learned: How very important it is to come together as a community. Montclair Village is an all-service, compact, eclectic and diverse area. This is our neighborhood, and Oakland is our city, and we have pride for both.”

Anticipating the Village plaza construction project’s pending launch and completion, Williams said the location will and allow for increased safety and access at future outdoor events.

“The association will be hosting city speaker events, children’s activities and business gatherings, the Beer and Wine Music Festival when it returns, the Lion’s Club Restaurant Walk and more.”

For full details on the 2021 Montclair Village Holiday Stroll, visit online.

Lou Fancher is a freelance writer. Contact her at

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Author: Lou Fancher