Starting Dec. 1, snow will fall on the front drive at Two Dole Drive every half hour from 5 to 8 p.m. It continues every evening through New Year's Day. That makes the Four Seasons Hotel Westlake Village driveway the most regular holiday event inside city limits this season, and the one you can visit on any night you choose.
Everything else on the local calendar has a fixed date. This year those dates pile up in the first week of December, and especially on Sunday, Dec. 6. That afternoon the Rotary Club of Westlake Village's holiday market is running its new second day, the city is holding its Sing-Along, and the snow at Dole Drive starts at 5 p.m. as usual. If you only plan one holiday day out this year, Sunday, Dec. 6 is the one that rewards planning.
A late-November tree lighting just over the line
The tree lighting closest to town takes place in late November at The Promenade at Westlake. The center carries the Westlake name, but Caruso lists it under Thousand Oaks. In its 2026 holiday announcement, Caruso puts the Annual Christmas Tree Lighting and Holiday Stroll on Friday, Nov. 20. The holiday market runs from 4 to 7 p.m. and the tree lighting follows at 7 p.m. The Promenade's own listing promises musical entertainment, Santa's arrival and a fireworks finale, plus strolling entertainment, kids' activities and a curated market with treats from the center's restaurants and shops. The Promenade's event page lists Saturday, Nov. 21, from 4 to 8 p.m., so check that page the week of the event for the final date and timing.
Santa's Cottage at The Promenade opens the next day and runs from Nov. 21 through Dec. 24. If you want to skate, go to The Lakes at Thousand Oaks instead. Its outdoor Holiday Ice Rink opened Nov. 6 and runs until Jan. 11, 2027.
While Santa's Cottage and the rink are running, the hotel on Dole Drive starts its own program on Dec. 1.
Inside city limits, the hotel runs the longest program
The Four Seasons is calling its 2026 season an Alpine-inspired winter village. General manager David Wilkie describes it in the hotel's festive season announcement as "a celebration designed for families, couples, and those looking to make the holidays truly unforgettable." The hotel says its workshops are meant for locals as well as hotel guests.
Food and drinks begin Dec. 1:
- Alpine Fondue at Prosperous Penny, the hotel's 1920s-inspired bar. It's Swiss Gruyere fondue with Red Fife sourdough croutons and Weiser Farms fingerling potatoes, served Monday through Friday for $55 for two, plus tax and gratuity.
- Après Ski Girl Dinner, also at Prosperous Penny. Caesar salad, fries with caviar and mimosa eggs, and steak tartare, Saturdays and Sundays from 5 p.m., $65 per person.
- Yakitori Nights at Onyx, robatayaki skewers of American Wagyu, Wednesday through Saturday from 5 p.m.
The hotel's workshops are booked through its Eventbrite page and spread across December.
| Date | Workshop | Price per person |
|---|---|---|
| Wed., Dec. 2 and Fri., Dec. 4, 5 p.m. | Wreath Making, ages 15 and up | $95 |
| Fri., Dec. 11, 6:30 p.m. | Floral & Flutes, centerpiece with champagne | $80 |
| Thu., Dec. 17, 5:30 p.m. | Behind the Line steak cooking class | $195 |
| Fri., Dec. 18, 5 p.m. | Paint & Sip | $65 |
| Tue., Dec. 22, 1 to 2:30 p.m. or 4 to 5:30 p.m. | Gingerbread Building and Photos with Santa | $55 |
Christmas Day brings two brunches, and the snowfall continues after that through Jan. 1. The Hamptons Christmas Day Brunch Buffet runs Friday, Dec. 25, from 11 a.m. to 3:30 p.m., with Santa from 12:30 to 2 p.m. It costs $250 for adults and $100 for children under 12, plus tax and gratuity, and reservations have been open on OpenTable since Sept. 25. Coin & Candor is serving a three-course prix fixe brunch that day from 11 a.m. to 4 p.m.
Notice that the wreath workshops fall on Dec. 2 and Dec. 4. They come just before the weekend when the rest of the area's holiday calendar arrives at once.
The Rotary market added a Sunday
Holidays in the Village, A European Marketplace, is presented by the Rotary Club of Westlake Village. It's held at The Oaks, 350 W. Hillcrest Drive in Thousand Oaks. In its fifth year, the festival is going from one day to two, according to Amigos805. It runs Saturday, Dec. 5, from 11 a.m. to 8 p.m. and Sunday, Dec. 6, from noon to 6 p.m. Admission and parking are free.
The same report says last year's one-day event drew more than 14,000 people. With a second day, that crowd now has two days to spread across. The marketplace has 60 artisan shops. Food and drink are served in the Festive Garden and La Place des Amis, including bratwurst, soft pretzels, French crepes and Glühwein. Sugar & Spice is the candy section, and Kris Kringle Village has face painting, Art Trek holiday crafts, a holiday train and a Village Bear Scavenger Hunt.
The Tannenbaum Christmas Tree Grove is new this year, set in the middle of the marketplace and run by the Thousand Oaks Elks Lodge. You choose a tree at the market and pick it up starting Dec. 7 at the Elks' tree lot at Carlson Building Materials, 1432 Thousand Oaks Blvd. Proceeds go to local charities. Rotary chair Mike Dutra told Amigos805 that visitors can "cross off items on your gift-giving list, enjoy great food, drinks and entertainment and be part of a wonderful community gathering."
The organizers' visitor page says Saturday late afternoon is the busiest stretch. If you'd rather avoid it, they suggest arriving when the gates open or after 6 p.m. The closest lots are on the west side of the property. The new Sunday has no evening hours, since the gates close at 6 p.m.
Sunday, Dec. 6 brings all three together
On the same Sunday, the City of Westlake Village and The Shoppes at Westlake Village hold the annual Holiday Sing-Along from 3 to 6 p.m. It's in the Fountain Courtyard at The Shoppes, 30770 Russell Ranch Road. Conejo Valley Guide's listing lists caroling and live music, a food drive for Manna, a holiday giving drive for Casa Pacifica, a book drive, raffle prizes, a photo booth, hot cocoa and face painting. The city posts updates at wlv.org/SingAlong.
Before this year, the Rotary market was a one-day event. This year its added Sunday runs at the same time as the city Sing-Along. The market's Sunday hours end at 6 p.m., the Sing-Along runs 3 to 6, and the Four Seasons snowfall starts at 5. So the afternoon works best in order, with the market first, the courtyard next and the driveway last.
| Time on Sun., Dec. 6 | Where | What's happening |
|---|---|---|
| Noon | The Oaks, 350 W. Hillcrest Dr., Thousand Oaks | Holidays in the Village opens for its second day |
| 3 p.m. | Fountain Courtyard, The Shoppes, 30770 Russell Ranch Rd. | City Holiday Sing-Along begins |
| 5 p.m. | Four Seasons Hotel Westlake Village, Two Dole Drive | First snowfall of the evening on the front drive, repeating every half hour |
| 6 p.m. | The Oaks and The Shoppes | Market and Sing-Along both end |
| 8 p.m. | Two Dole Drive | Last snowfall of the evening |
If you'd like to bring donations to the Sing-Along, pack the cans for Manna and the books for the drive before you leave for The Oaks. Bought a tree at the Tannenbaum Grove that weekend? It's ready for pickup at Carlson Building Materials the next morning.
Saturday, Dec. 5 is also an option for the market. It has the longer hours, open until 8 p.m., but the organizers expect the late afternoon to be the most crowded time. Pick Sunday if you want the shorter market day plus the Sing-Along. Pick Saturday if you want the market by itself and later hours.
Holiday plans and home plans often come up in the same conversation this time of year, especially when family is in town for the Sing-Along or the snow on Dole Drive. If you're thinking about how this season fits into your next few years in Westlake Village, I'm always happy to talk it through. Cris Epstein is glad to help, so let's connect.
